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[ CAS No. 70-23-5 ] {[proInfo.proName]}

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Chemical Structure| 70-23-5

Chemical Structure| 70-23-5

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Quality Control of [ 70-23-5 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 70-23-5 ]

Product Citations

Product Citations Expand+

Single-Source Precursors for the Controlled Aqueous Synthesis of Bismuth Oxyhalides

Gordon, Matthew N. ; Liu, Yanyao ; Brown, M. Kevin , et al. Inorg. Chem.,2023,62(24):9640-9648. DOI: 10.1021/acs.inorgchem.3c01114 PubMed ID: 37265371

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Abstract: Bismuth oxyhalides are a promising class of photocatalysts for harvesting solar energy. These materials are often synthesized in aqueous media with poor synthetic control resulting from the extremely fast nucleation and growth rates of the particles. These fast rates are caused by the rapid precipitation of bismuth salts with free halide ions. We have developed water-soluble precursors combining bismuth with either chlorine or bromine atoms in the same metal-organic complex. With the application of heat, halide ions are released, which then precipitate with bismuth ions as BiOX (X = Cl, Br). By controlling the halide ion formation rate, the nucleation and growth rates of BiOX materials can be tuned to provide synthetic control. The diverse potential of these precursors is demonstrated by synthesizing BiOX in three ways: aqueous colloidal synthesis, solid-state decomposition, and fabrication of films of BiOX via spray pyrolysis of the aqueous precursor solutions. These broadly applicable single-source precursors will enhance the ability to synthesize future BiOX materials with controlled morphologies.

Purchased from AmBeed: 70-23-5

Indole C6 Functionalization of Tryprostatin B Using Prenyltransferase CdpNPT

Gardner, Eric D. ; Dimas, Dustin A. ; Finneran, Matthew C. , et al. Catalysts,2020,10(11):1247. DOI: 10.3390/catal10111247 PubMed ID: 33643664

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Abstract: Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization However, the inability to perform late-stage modification of the indole ring has limited the structure-activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymic approach for the late-stage modification of tryprostatin B using a cyclic dipeptide N-prenyltransferase (CdpNPT) from Aspergillus fumigatus, which generates novel analogs functionalized with allylic, benzylic, heterocyclic, and diene moieties. Notably, this biocatalytic functionalizational study revealed high selectivity for the indole C6 position. Seven of the 11 structurally characterized analogs were exclusively C6-alkylated, and the remaining four contained predominant C6-regioisomers. Of the 24 accepted substrates, 10 provided >50% conversion and eight provided 20-50% conversion, with the remaining six giving <20% conversion under standard conditions. This study demonstrates that prenyltransferase-based late-stage diversification enables direct access to previously inaccessible natural product analogs.

Keywords: biocatalysts ; chemoenzymatic synthesis ; late-stage functionalization ; prenyltransferase ; tryprostatin

Purchased from AmBeed: 71989-31-6 ; 3189-13-7 ; 3945-69-5 ; 70-23-5 ; 556-82-1

Product Details of [ 70-23-5 ]

CAS No. :	70-23-5	MDL No. :	MFCD00000204
Formula :	C₅H₇BrO₃	Boiling Point :	No data available
Linear Structure Formula :	BrCH₂COCO₂C₂H₅	InChI Key :	VICYTAYPKBLQFB-UHFFFAOYSA-N
M.W :	195.01	Pubchem ID :	66144
Synonyms :

Calculated chemistry of [ 70-23-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	35.5
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	0.51
Log Po/w (MLOGP) :	0.46
Log Po/w (SILICOS-IT) :	1.01
Consensus Log Po/w :	0.93

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.52
Solubility :	5.95 mg/ml ; 0.0305 mol/l
Class :	Very soluble
Log S (Ali) :	-1.67
Solubility :	4.21 mg/ml ; 0.0216 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.57
Solubility :	5.24 mg/ml ; 0.0269 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.99

Safety of [ 70-23-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501	UN#:	3265
Hazard Statements:	H302+H312-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 70-23-5 ]

* 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 [ 70-23-5 ]
Downstream synthetic route of [ 70-23-5 ]

[ 70-23-5 ] Synthesis Path-Upstream 1~1

1
[ 70-23-5 ]
[ 24241-18-7 ]
[ 87597-21-5 ]

Yield	Reaction Conditions	Operation in experiment
50.6%	at 20 - 110℃;	Step A: Preparation of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10 C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a2(S0₄) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz, CDCl₃): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6%	at 110℃; for 3 h;	Step A: Preparation of ethyl 6,8-dibromoimidazo[ 1 , 2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3, 5-dibrompyrazine (20 g, 79mmol) in dimethyicarbonate (1 33 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na₂(S0₄) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz, CDC ): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6%	at 20 - 110℃; for 3 h;	Intermediate Example 1 -2: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2- yl)methanolStep A: Preparation of ethyl 6,8-dibromoimidazo[1 , 2-a]pyrazi^'ne-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a₂(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz, CDCI3): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.

50.6%	at 110℃;	Step A: Preparation of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3,5-di brom pyrazi ne (20 g, 79m mol ) i n dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na₂(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 3/4) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz, CDCl₃): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6%	at 20 - 110℃;	To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110° C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na₂(SO₄) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6percent) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz,
50.6%	at 110℃; for 3 h;	To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110° C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na₂(SO₄) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6percent) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: ¹H-NMR (300 MHz, CDCl₃: δ=8.30 (s, 1H), 8.27 (s, 1H), 4.48 (q, 2H), 1.43 (tr, 3H) ppm.

Reference： [1] Patent: WO2012/80232, 2012, A1, . Location in patent: Page/Page column 36-37
[2] Patent: WO2012/80228, 2012, A1, . Location in patent: Page/Page column 42-43
[3] Patent: WO2012/80234, 2012, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2012/80236, 2012, A1, . Location in patent: Page/Page column 64
[5] Patent: US2013/281460, 2013, A1, . Location in patent: Paragraph 0270-0271
[6] Patent: US2013/267527, 2013, A1, . Location in patent: Paragraph 0245-0246

[ 70-23-5 ] Synthesis Path-Downstream 1~3

1
[ 70-23-5 ]
[ 62-55-5 ]
[ 79836-78-5 ]

Reference： [1]Patent: EP1186604,2002,A1 .Location in patent: Page 110

2
[ 70-23-5 ]
[ 42182-27-4 ]
[ 1354555-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃;	Synthesis of 7-cyano-imidazo[l,2-a]pyridine-2-carboxylic acid and 7-carbamoyl- imidazo[l,2-a]pyridine-2-carboxylic acid; To a solution of <strong>[42182-27-4]2-amino-4-cyanopyridine</strong> (4.00 g, 33.6 mmol) in THF (100 mL) add ethyl bromopyruvate (6.55 g, 33.6 mmol). Stir the mixture at rt overnight. A light yellow suspension forms. After filtration and washing with THF, dissolve the light yellow solid in EtOH (50 mL) and heat to reflux for 4 h. Concentrate in vacuo to afford the desired product 7-cyano-imidazo[l,2-a]pyridine-2-carboxylic acid ethyl ester as a solid (6.21 g, 28.9 mmol).

Reference： [1]Patent: WO2012/6203,2012,A1 .Location in patent: Page/Page column 59

3
[ 70-23-5 ]
[ 17583-10-7 ]
ethyl 9-oxo-7-thia-2,5-diazatricyclo[6.4.0.0²^,⁶]dodeca-1⁽⁸⁾,3,5-triene-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 75 - 80℃; for 1h;	Example 83 Ethyl 9-oxo-7-thia-2,5-diazatricyclo[6.4.0.02'6]dodeca-l(8),3,5-triene-4-carboxylate Ethyl 3-bromo-2-oxopropanoate (3.85 mL, 30.5 mmol) was added dropwise to a solution of 2-amino-4,5,6,7-tetrahydro-l,3-benzothiazol-7-one (4.27 g, 25.4 mmol) in anhydrous DMF (90 mL) and stirred at 75-80°C for 60 min. The solution was cooled to room temperature and about half of the solvent was removed under reduced pressure. The remaining solution was diluted with EtOAc (100 mL) and washed with water (5 x 100 mL). The organic layer was concentrated in vacuo to yield a yellow residue which was chromatographed on silica (eluent: 50 to 90percent EtOAc in heptane) to afford the title compound as a yellow solid (2.60g, 74percent purity, 29percent yield); 1H NMR (250 MHz, DMSO-d6) delta 1.31 (t, 3H), 2.23 (p, 2H), 2.57 - 2.70 (m, 2H), 3.12 (t, 2H), 4.30 (q, 2H), 8.69 (s, 1H).

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2764 - 2778
[2]Patent: WO2016/42172,2016,A1 .Location in patent: Page/Page column 125

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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

Ghs Hazard Statements

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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