[ CAS No. 77-92-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 77-92-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 77-92-9 ]

SDS Specification

Alternatived Products of [ 77-92-9 ]

Product Details of [ 77-92-9 ]

CAS No. :	77-92-9	MDL No. :	MFCD00011669
Formula :	C₆H₈O₇	Boiling Point :	-
Linear Structure Formula :	HOC(COOH)(CH₂CO₂H)₂	InChI Key :	KRKNYBCHXYNGOX-UHFFFAOYSA-N
M.W :	192.12	Pubchem ID :	311
Synonyms :		Chemical Name :	2-Hydroxypropane-1,2,3-tricarboxylic acid

Calculated chemistry of [ 77-92-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	7.0
Num. H-bond donors :	4.0
Molar Refractivity :	37.47
TPSA :	132.13 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-1.49
Log Po/w (XLOGP3) :	-1.72
Log Po/w (WLOGP) :	-1.25
Log Po/w (MLOGP) :	-1.48
Log Po/w (SILICOS-IT) :	-1.6
Consensus Log Po/w :	-1.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	0.38
Solubility :	463.0 mg/ml ; 2.41 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.54
Solubility :	55.3 mg/ml ; 0.288 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.71
Solubility :	9900.0 mg/ml ; 51.5 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.18

Safety of [ 77-92-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P304+P340+P312-P305+P351+P338-P337+P313-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77-92-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 77-92-9 ]
Downstream synthetic route of [ 77-92-9 ]

[ 77-92-9 ] Synthesis Path-Upstream 1~5

1
[ 77-92-9 ]
[ 71-36-3 ]
[ 77-94-1 ]

Yield	Reaction Conditions	Operation in experiment
95.3%	Stage #1: at 80℃; for 3 h; Inert atmosphere Stage #2: at 130℃;	Step 1, Preparation of choline-based acidic ionic liquid: 0.5mol choline chloride was heated under agitation flask was added 500mL, 0.25mol of citric acid was added, under a nitrogen atmosphere, the conditions of temperature 80 3h, after cooling to give choline-based acidic ionic liquid;Step 2, the esterification reaction: to a stirred with a mechanical, a thermometer, a reflux condenser and a four-necked flask was added 1.0mol trap n-butanol and a step in the choline-based acidic ionic liquid was heated to reflux with stirring the reaction water was separated from the trap, the reaction of the reaction to dryness stopped when re-entering the trap, choline chloride precipitates from the reaction system; the stirring was heated at reflux temperature of 130 , the stirring rate to 1000rpm;Step 3, separated choline chloride: The reaction system of Step II reaction was filtered to obtain a solid product and a liquid phase of choline chloride;Step 4, tributyl citrate purification: step 3 of the liquid product was subjected to atmospheric distillation, and then using mass concentration of 8percent NaHCO₃Mass concentration of the solution or NaOH solution (also can be mass concentration of 1percent to 3percent of 1percent to 5percent Na₂CO₃Alternatively the solution pH) after the residue was washed atmospheric distillation residue to a value of 6, followed by activated carbon was added to the residue decolorized after washing, the activated carbon was removed by filtration, and then the residue was distilled under reduced pressure after filtration, the pressure is 260 Pa, the fraction collected 197 ~ 200 obtain tributyl citrate; the atmospheric distillation temperature of 119 deg.] C; mass of the activated carbon was 5.0percent by mass of citric acid in step a.
94.1%	at 95 - 143℃; for 6.33333 h;	A 1 L four-necked flask equipped with a stirrer, thermometer, condenser and distillate receiver was charged with 192.0 g (1.0 mole) of anhydrous citric acid, 267.0 g (3.6 moles) of butanol and 1.9 g of sulfuric acid. The mixture was heated to 95°C over a period of 20 minutes while being stirred at atmospheric pressure. While recovering butanol and water generated as by-products of esterification in the receiver, stirring was continued for 3 hours until the reaction temperature reached 105°C. Subsequently, while recovering butanol and water generated as by-products of esterification in the receiver, 222.0 g (3.0 moles) of additional butanol was added at a reaction temperature of 101 to 143°C over a period of 3 hours to complete the reaction. After the completion of the reaction, the reaction product was cooled to 60°C, and at the same temperature (60°C), neutralized by adding sodium carbonate in an amount corresponding to twice the acid value of the reaction product (i.e., 2.0 g) and 120.0 g of water. Subsequently, the organic layer was washed with 120.0 g of water and heated to 120°C. Excess butanol was recovered until the pressure reached about 4 kPa, and steam distillation was performed at the same pressure at 120°C for 1 hour to remove low-boiling components from the reaction product, to thereby obtain 329.0 g of a colorless transparent liquid. The yield was 94.1percent and the acid value of the product was 0.025 (mg KOH/g).
84.4%	With toluene-4-sulfonic acid In toluene at 90 - 110℃; for 4 h;	With a stirrer,Trap,Snake-shaped condenser,Necked flask equipped with a stirrer and a thermometer, 3.6 mol (266.4 g) of n-butanol was added,Citric acid 0.6 mol (210 g),P-toluenesulfonic acid (9.53 g)Toluene 50 ml.During heating from 90 ° C to 110 ° C,From the first drop of water began to reflux for 4 hours.During the reaction, the lower water layer of the water separator was continuously released and measured with a graduated cylinderWater quantity.After the esterification reaction, the excess toluene and ethanol were distilled off under reduced pressure,The reaction product is then distilled under reduced pressure to give tributyl citrate.After completion of the reaction,The product esterification rate was 96.3percentThe yield of tributyl citrate was 84.4percent.

Reference： [1] Tetrahedron, 2006, vol. 62, # 2-3, p. 422 - 433
[2] RSC Advances, 2018, vol. 8, # 66, p. 37835 - 37840
[3] Angewandte Chemie - International Edition, 2009, vol. 48, # 1, p. 168 - 171
[4] Green Chemistry, 2014, vol. 16, # 11, p. 4649 - 4653
[5] Patent: CN104447306, 2016, B, . Location in patent: Paragraph 0044-0048; 0052
[6] Patent: EP1491523, 2004, A1, . Location in patent: Page 16
[7] RSC Advances, 2014, vol. 4, # 100, p. 57297 - 57307
[8] Patent: CN106278881, 2017, A, . Location in patent: Paragraph 0017; 0018
[9] Archives of Biochemistry, 1950, vol. 28, p. 274,275
[10] Industrial and Engineering Chemistry, 1955, vol. 47, p. 797
[11] Journal of Pharmacy and Pharmacology, 1950, vol. 2, p. 229
[12] Bulletin of the Chemical Society of Ethiopia, 2011, vol. 25, # 1, p. 147 - 150

2
[ 77-92-9 ]
[ 71-36-3 ]
[ 118068-28-3 ]
[ 142-96-1 ]
[ 77-94-1 ]
[ 101996-65-0 ]

Reference： [1] Patent: EP1849764, 2007, A1, . Location in patent: Page/Page column 21-22

3
[ 7664-93-9 ]
[ 77-92-9 ]
[ 71-36-3 ]
[ 77-94-1 ]

Reference： [1] Industrial and Engineering Chemistry, 1955, vol. 47, p. 797

4
[ 748-97-0 ]
[ 77-92-9 ]
[ 54965-24-1 ]
[ 54965-24-1 ]

Yield	Reaction Conditions	Operation in experiment
7.5 g	Stage #1: With hydrogenchloride In water; isopropyl alcohol for 5 h; Reflux Stage #2: at -5 - 10℃; for 10 h;	1) 20 g of raw material (formula I) was added to the three-necked flask, 180 ml of isopropyl alcohol was added, dissolved by stirring, 50 ml of hydrochloric acid was added, and the mixture was heated under reflux for 5 hours. HPLC to monitor the E isomer greater than 35percent (HPLC Figure 1), cooled to room temperature crystallization 2h, Filtration, filter cake can be recycled, the filtrate by adding 120ml of water, if solid, filter, take the filtrate, adjust the pH to sodium with sodium hydroxide, There is a solid precipitation, extracted with ethyl acetate to the organic layer without obvious color, pure water to weak alkaline, Dried over anhydrous sodium sulfate and filtered to dryness to give 10 g of an oily substance, i.e., a mixture of Z-tamoxifen and e-tamoxifen, with an E isomer content greater than 65percent (HPLC Figure 2); 10 ml of the above sample was added with 10 ml of acetone. After stirring and stirring, 5 g of citric acid was added, stirred and dissolved, cooled at -5-10 ° C for 10 h, The filter cake was washed with acetone to give 12 g of a mixture of tamoxifen citrate and tamoxifen citrate (E isomer content greater than 70percent) (HPLC Figure 3); Take the above 12g solid, add 60ml of water and 12ml of ethanol, dissolved in activated carbon after decolorization 0.5h, hot filter, the filtrate -5-25 ° C cooling crystallization, Filtration, filter cake with acetone beating washing, drying, 8g E-tamoxifen citrate (content greater than 98.5percent, HPLC shown in Figure 4); according to the above method for secondary recrystallization, So that 7.5gE-tamoxifen citrate (content of more than 99.5percent, HPLC Figure shown in Figure 5).

Reference： [1] Patent: CN103992234, 2016, B, . Location in patent: Paragraph 0055-0059

5
[ 10540-29-1 ]
[ 77-92-9 ]
[ 54965-24-1 ]

Reference： [1] Pharmaceutical Research, 2006, vol. 23, # 4, p. 806 - 812

[ 77-92-9 ] Synthesis Path-Downstream 1~10

1
[ 20150-34-9 ]
[ 77-92-9 ]
ferrous bisglycinate citrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 55 - 60℃; for 4.0h;	One mole of ferrous oxide is reacted with two moles of sodium glycinate in the presence of citric acid in an aqueous solution to form <strong>[20150-34-9]ferrous bisglycinate</strong>. The <strong>[20150-34-9]ferrous bisglycinate</strong> is further reacted in a 1:1 molar ratio with citric acid to form <strong>[20150-34-9]ferrous bisglycinate</strong> citric acid chelate. Specifically, two moles of sodium glycinate (194.1 g) were dissolved in one liter of 0.5 M citric acid, and the mixture was brought to 55-60° C. Next, 1.0 mole (71.8 g) of ferrous oxide was added to the mixture, and the mixture was allowed to react for 1 hour forming <strong>[20150-34-9]ferrous bisglycinate</strong>. Next, one mole of citric acid (192.1 g) was added to the reaction mixture. After a 4 hour reaction time, the composition was cooled 40° C. and spray dried to obtain about 394.0 g of <strong>[20150-34-9]ferrous bisglycinate</strong> citrate at 100percent yield.

Reference： [1]Patent: US2007/270591,2007,A1 .Location in patent: Page/Page column 5

2
[ 34846-90-7 ]
[ 19472-74-3 ]
[ 77-92-9 ]
4-(2-bromo-phenyl)-4-cyano-but-3-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium chloride; sodium t-butanolate; In tetrahydrofuran;	Example 3 4-(2-BROMO-PHENYL)-4-CYANO-BUT-3-ENOIC ACID METHYL ESTER A solution of 2-bromo-phenylacetonitrile (6.62 mL, 51.0 mmol) and methyl-3-methoxyacrylate (5.32 mL, 49.5 mmol) in tetrahydrofuran (10 ml) was added to a suspension of sodium tert-butoxide (5.05 g, 51.0 mmol) in tetrahydrofuran (70 mL) at 0° C. over 10 minutes under a stream of nitrogen. The reaction mixture was warmed to room temperature and after 15 minutes diluted with methyl tert-butyl ether (240 mL). To the mixture was added 0.2 N aqueous citric acid until the aqueous layer had a pH of 2 (80 mL). The organic layer was separated and washed with a saturated aqueous solution of sodium chloride (2*80 mL), dried over anhydrous sodium sulfate, filtered through a pad of Celite and silica (4:1) and concentrated in vacuo to provide 4-(2-bromo-phenyl)-4-cyano-but-3-enoic acid methyl ester as a pale yellow oil (13.8 g, 96percent). Major isomer 1H NMR (400 MHz, CDCl3) delta7.59 (dd, 1H, J =7.6, 1.2), 7.57-719 (m, 3H), 6.71 (t, 1H, J=7.1), 3.71 (s, 3H), 3.61 (d, 2H, J=7.1); 13C NMR (100 MHz, CDCl3) delta169.7, 144.4, 133.7, 131.4, 131.1, 128.3, 122.5, 118.1, 117.3, 115.3, 52.7, 36.6; IR (ATR, neat) 1737, 1434, 1319, 1199, 1171, 1026, 755 cm-1. Minor isomer 1H NMR (400 MHz, CDCl3) delta7.61 (dd, 1H, J=7.6, 1.0), 7.57-7.19 (m, 3H), 6.9 (t,1H, J=7.5), 3.64 (s, 3H), 3.06 (d, 2H, J=7.5).

Reference： [1]Patent: US2003/60624,2003,A1

3
[ 6066-82-6 ]
[ 20806-43-3 ]
[ 77-92-9 ]
N-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]-β-D-phenylalanine diphenylmethyl ester hydrochloride [ No CAS ]
[ 219812-98-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;palladium dihydroxide; In N-methyl-acetamide; methanol; acetonitrile;	EXAMPLE 24 (S)-3-[(2S,3R,4R,5S)-5-(O-benzyl-L-seryl)amino-2,3,4 6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid To a solution of O-benzyl-N-benzyloxycarbonyl-L-serine (329 mg) in acetonitrile (5 ml) were added N-hydroxysuccinimide (115 mg) and N,N'-dicyclohexylcarbodimide (206 mg) at room temperature and the mixture was stirred at room temperature for 3 hours. The formed insoluble solid was filtrated off and the filtrate was concentrated under reduced pressure. The residue was dissolved in dimethylformamide (5 ml), followed by addition of triethylamine (0.139 ml) and diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate hydrochloride (545 mg) at room temperature and stirred at room temperature for 15 hours. To the mixture was added 10% aqueous citric acid solution and the whole was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively and dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was subjected to flush silica gel column chromatography, followed by elution with methanol-ethyl acetate (1:20). The effective fractions were combined and concentrated under reduced pressure. The residue was dissolved in methanol (30 ml) and stirred at room temperature with palladium hydroxide on carbon (100 mg) under hydrogen atmosphere(3-4 atm) at room temperature for 6 hours. After filtration, the filtrate was concentrated under reduced pressure to give a residue, which was passed through a column of DIAION CHP-20P (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-diethylether to afford the title compound (97 mg). 1H-NMR(DMSO-d6) delta: 2.55-2.90(2H,m), 3.20-5.40(10H,m), 4.50(2H,s), 7.10-7.50(10H,m), 7.84(1H,d,J=8.8 Hz), 8.29(1H,d,J=11.4 Hz).

Reference： [1]Patent: US6423869,2002,B1

4
[ 248921-66-6 ]
[ 56602-33-6 ]
[ 86499-35-6 ]
[ 77-92-9 ]
[ 145486-02-8 ]

Yield	Reaction Conditions	Operation in experiment
480 mg (100%)	With triethylamine; In dichloromethane; ethyl acetate;	Step A: 2(R)-t-Butoxycarbonylamino-3-(t-butoxy)-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide To a solution of 200 mg (1.13 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step B) in 8 mL of dry methylene chloride was added 0.206 mL (1.48 mmol) of triethylamine, 553 mg (1.25 mmol) of <strong>[248921-66-6]BOC-D-serine t-butyl ether</strong> followed by 602 mg (1.36 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate. The reaction mixture was stirred at room temperature for 2 hours then diluted with 100 mL of ethyl acetate, washed with 25 mL of 5% aqueous citric acid, 25 mL of saturated sodium bicarbonate and 25 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvents removed under vacuum. The residue was purified by flash chromatography on silica gel, eluding with ethyl acetate/hexane (55:45) to afford 480 mg (100%) of the product as a white foam. 1 H NMR (200 MHz,CDCl3): 1.20 (s,9H), 1.47 (s,9H), 1.92 (m,1H), 2.55-3.02 (m,3H), 3.38 (t,8 Hz,1H), 3.78 (m,1H), 4.15 (m,1H), 4.52 (m,1H), 5.45 (s,1H), 7.00 (m,1H), 7.10-7.35 (m,3H), 7.68 (d,4 Hz,1H), 8.05 (s,1H). FAB-MS: calculated for C22 H33 N3 O5 419; found 420 (M+H,20%), 426 (M+Li,40%).

Reference： [1]Patent: US5206235,1993,A

5
[ 4530-20-5 ]
[ 2886-33-1 ]
[ 144-55-8 ]
[ 77-92-9 ]
[ 543-27-1 ]
[ 56612-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In ethyl acetate; N,N-dimethyl-formamide;	1. t-Butyloxycarbonyl-glycyl-L-aspartic acid dibenzyl ester t-Butyloxycarbonyl-glycine (7.1 g) was dissolved in ethyl acetate (50 ml), cooled to -10 to -15 C. with stirring and treated with N-methylmorpholine (5.6 ml) followed by isobutyl chloroformate (5.18 ml). The mixture was stirred at -15 C. for 10 minutes. Meanwhile, L-aspartic acid dibenzyl ester p-tosylate salt (2.1 g) was dissolved in dimethyl formamide (80 ml), cooled to -10 C. and neutralized by adding N-methylmorpholine (5.6 ml). This solution was added to the above solution of the preformed mixed anhydride and the reaction mixture allowed to warm slowly to room temperature with stirring over 3 hours. The reaction mixture was then diluted with ethyl acetate (300 ml) and the solution washed with brine (twice) followed by 4% aqueous sodium bicarbonate, water, 5% aqueous citric acid and finally with water to neutrality. The organic phase was dried (magnesium sulfate) and then evaporated to an oil. Yield: 20 g. The product was homogeneous by TLC (System: chloroform:methanol:acetic acid, 360:32:8; Rf =0.8).

Reference： [1]Patent: US4929601,1990,A

6
[ 34619-03-9 ]
[ 2799-07-7 ]
[ 101-83-7 ]
[ 77-92-9 ]
[ 26988-59-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In 1,4-dioxane;	A. N-boc-S-trityl-cysteine, dicyclohexylammonium salt (XX) To a solution of S-trityl cysteine (see Hiskey and Adams, J. Org. Chem., 30:1340, (1965)) (36.3 g, 0.10 mol) in dioxane (200 ml) and 1M aqueous NaOH (100 ml, 0.10 mol) was added di-t-butyl carbonate (25.36 g, 0.12 mol). The resulting opaque solution became warm and effervesced and the pH fell from 12 to 8 over one hour. After stirring for 90 min, 50percent aqueous citric acid (40 ml) was added and the resulting mixture (pH 4) was extracted with ether. The ether was washed with water, then saturated brine, dried (MgSO4), filtered and evaporated to give N-BOC-S-(triphenylmethyl)-cysteine as an oil. Half of this material was dissolved in ether (200 ml) and treated with dicyclohexylamine (10 ml, 50 mmol) to give compound (XX) as a white precipitate which was filtered off, washed with ether and dried (25.1 g, 78percent), mp 205°-207°.

Reference： [1]Patent: US4673562,1987,A

7
[ 443-82-3 ]
[ 77-92-9 ]
[ 1190890-19-7 ]

Yield	Reaction Conditions	Operation in experiment
19%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	Step Atert-butyl (4-fluoro-1,3-dihydro-2H-isoindol-2-yl)methylcarbamate3-Fluoro-ortho-xylene (1.99 g, 16.03 mmol), N-bromosuccinimide (6.98 g, 39.22 mmol) and benzoyl peroxide (0.24 g) were added to carbon tetrachloride (60 ml), and the mixture was heated under reflux for 45 min.The reaction mixture was cooled, diluted with hexane, and the insoluble material was filtered off.The obtained solution was concentrated under reduced pressure.Using the obtained oil, the reaction was performed according to the method of Reference Example 17, step B.After completion of the reaction, 10percent aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane=1:1 mixed solvent, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate.The insoluble material was filtered off, and the solution was concentrated under reduced pressure.The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (826 mg, yield 19percent) as a pale-yellow oil.1H-NMR (300 MHz, CDCl3); delta(ppm) 1.41 (s, 9H), 3.09 (s, 3H), 4.47 (s, 2H), 4.48 (s, 2H), 6.87 (t, J=8.6, 1H), 6.94 (d, J=7.2, 1H), 7.1-7.2 (m, 1H).

Reference： [1]Patent: US2012/196824,2012,A1

8
[ 14769-73-4 ]
[ 77-92-9 ]
[ 32339-82-5 ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 634 - 640

9
[ 77-92-9 ]
[ 851983-85-2 ]
(3β)-17-(1H-benzimidazol-1-yl)androst-5,16-dien-3-ol citrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 25℃; for 12h;	202.7 mg of the compound of the formula (I) was suspended in 10 mL of acetonitrile, 119.0 mg of citric acid was added and the mixture was stirred at room temperature (25 ± 2C) for 12 hours, and the solid was collected.

Reference： [1]Patent: CN105732759,2016,A .Location in patent: Paragraph 0130; 0131; 0132

10
[ 247069-27-8 ]
[ 18621-18-6 ]
[ 101799-75-1 ]
[ 77-92-9 ]
[ 442526-91-2 ]

Yield	Reaction Conditions	Operation in experiment
93.58%		Ethyl 2,4,5-trifluorobenzoylacetate (20.0 g, 0.081 mol) was added to a 250 mL reaction flask.Triethylorthoformate (21.6 mL, 0.130 mol), acetic anhydride (32.5 mL, 0.344 mol), stirring,Heating was started and the temperature of the feed was raised to 130 C. for 4.0 hours.After the reaction was completed, the solvent was distilled off under reduced pressure to obtain an oily liquid.Add 70 mL of N-methylpyrrolidone to make the oily liquidThe solution was dissolved, <strong>[247069-27-8]3,5-difluoro-2,6-diaminopyridine</strong> (13.8 g, 0.095 mol) was added, and the feed solution was warmed to 50C.Stir and stir for 1.5h. After the addition of anhydrous lithium chloride (6.12 g, 0.146 mol), DBU (11.37 g, 0.075 mol) was added, and the reaction temperature was controlled at 35 C. for 2.0 h.3-Hydroxyazetidine hydrochloride (8.45 g, 0.077 mol) was added, DBU (26.82 g, 0.176 mol) was slowly added, and the temperature was 35 C. for 2.5 h.After the reaction is complete, transfer to a 500 mL reaction flask and add 25 mL of ethyl acetate.Slowly add 145 mL of 10% citric acid solution.After the addition was completed, the temperature was adjusted to 20C, and the crystals were crystallized for 4.0 hours. The crystals were collected, and the mixture was collected by suction filtration. The cake was collected and dried in an oven at 60C to obtain 38.35 g of the intermediate I. The yield was 93.58%.

Reference： [1]Patent: CN107778293,2018,A .Location in patent: Paragraph 0035; 0036

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Technical Information

? Appel Reaction ? Arndt-Eistert Homologation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Heat of Combustion ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Jones Oxidation ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Preparation of Alcohols ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alcohols ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Ritter Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Swern Oxidation ? Ugi Reaction

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Sodium 2-hydroxypropane-1,2,3-tricarboxylate

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[ 18996-35-5 ]

Sodium 3,4-dicarboxy-3-hydroxybutanoate

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[ 13748-90-8 ]

(S)-2-Hydroxy-4-methylpentanoic acid

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Alcohols

[ 6100-05-6 ]

Potassium 2-hydroxypropane-1,2,3-tricarboxylate hydrate

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[ 3458-72-8 ]

2-Hydroxy-1,2,3-propanetricarboxylic acid triammonium salt

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Sodium 2-hydroxypropane-1,2,3-tricarboxylate

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Sodium 3,4-dicarboxy-3-hydroxybutanoate

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[ 77-95-2 ]

(1α,3R,4α,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid

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Sodium 3,4-dicarboxy-3-hydroxybutanoate

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1-Hydroxycyclohexanecarboxylic acid

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 77-92-9 ] {[proInfo.proName]}

Quality Control of [ 77-92-9 ]

Related Doc. of [ 77-92-9 ]

Product Details of [ 77-92-9 ]

Calculated chemistry of [ 77-92-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 77-92-9 ]

Application In Synthesis of [ 77-92-9 ]

[ 77-92-9 ] Synthesis Path-Upstream 1~5

[ 77-92-9 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 77-92-9 ]

Aliphatic Chain Hydrocarbons

Alcohols

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 77-92-9 ]