[ CAS No. 541-59-3 ] {[proInfo.proName]}

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Quality Control of [ 541-59-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 541-59-3 ]

SDS Specification

Alternatived Products of [ 541-59-3 ]

Product Details of [ 541-59-3 ]

CAS No. :	541-59-3	MDL No. :
Formula :	C₄H₃NO₂	Boiling Point :	-
Linear Structure Formula :	HN(CO)₂C₂H₂	InChI Key :	PEEHTFAAVSWFBL-UHFFFAOYSA-N
M.W :	97.07	Pubchem ID :	10935
Synonyms :		Chemical Name :	1H-Pyrrole-2,5-dione

Calculated chemistry of [ 541-59-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	25.87
TPSA :	46.17 ?2

Pharmacokinetics

GI absorption :	High
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) :	-7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.5
Log Po/w (XLOGP3) :	-0.29
Log Po/w (WLOGP) :	-1.18
Log Po/w (MLOGP) :	-0.58
Log Po/w (SILICOS-IT) :	0.34
Consensus Log Po/w :	-0.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.26
Solubility :	53.4 mg/ml ; 0.551 mol/l
Class :	Very soluble
Log S (Ali) :	-0.22
Solubility :	58.5 mg/ml ; 0.603 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.27
Solubility :	52.6 mg/ml ; 0.542 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 541-59-3 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P501-P272-P260-P270-P264-P280-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	2923
Hazard Statements:	H301-H314-H317	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 541-59-3 ]

* 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 [ 541-59-3 ]
Downstream synthetic route of [ 541-59-3 ]

[ 541-59-3 ] Synthesis Path-Upstream 1~1

1
[ 541-59-3 ]
[ 399-52-0 ]
[ 198474-05-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With zinc(II) chloride In acetonitrile at 85℃; for 24.1667 h;	Alternatively, a mixture of 5-fluoroindole (5.00 g, 5.00 g, 35.5 mmol, 96 mass percent, 1.00) and maleimide (1.5 equiv., 5.17 g, 53.3 mmol, 1.50) was charged in a 50 mL vessel, and then acetonitrile (3 L/kg, 15.0 mL, 1 1.7 g, 286 mmol, 100 mass percent) and zinc chloride (1.05 equiv., 5.08 g, 37.3 mmol, 100 mass percent) were added. The reaction was heated to 85°C over 10 min and then maintained at 85°C for 24 hrs. While still at 85 °C, water (6 L/kg, 30.0 mL, 30.0 g, 1670 mmol, 100 mass percent) was added slowly, while maintaining the temperature above 80°C. Yellow solids precipitated. The reaction mixture was cooled to 50°C over 1 hour followed by stirring at 50°C for 2 hours, then cooled 10°C over 1 hour. The reaction was stirred at 10°C for 1 hour. The solids were filtered off, then the filter cake was washed 2 times with 5 ml 1 :1 ACN/water to afford isolated compound (6.85 g, 6.85 g, 29.5 mmol, 83.1 percent Yield). For purification, the resulting isolated compound was charged (6.85 g, 6.85 g, 29.5 mmol, 100 mass percent) into a vessel, followed by addition of tetrahydrofuran (6 L/kg, 41.1 mL, 36.4 g, 505 mmol, 100 mass percent). This mixture was heated to 66°C to form a homogeneous solution. Heptane (4 L/kg, 27.4 mL, 18.7 g, 187 mmol, 100 mass percent, was added slowly at 66°C ; solids began to precipitate after 5 volumes. The mixture was cooled to 25°C over 3 hours, then filtered and washed with heptane, followed by drying in the high vacuum oven overnight. Isolated compound (4.93 g, 4.93 g, 21.2 mmol, 100 mass percent, 72.0percent Yield). This isolated compound is charged 2 (1.00 g, 4.3 mmol, 100 mass percent,) into a 50ml vessel and tetrahydrofuran (6 L/kg, 6 mL, 100 mass percent) and heptane (6 L/kg, 6 mL, 100 mass percent) were added. The slurry was stirred at 25°C for 48 hrs. The solids were filtered off and dried in the high vacuum oven overnight. The Isolated compound : (0.89 g, 3.83 mmol, 100 mass percent, 89.00percent Yield).
83.1%	With zinc(II) chloride In acetonitrile at 85℃; for 24 h;	Route B: (0356) Alternatively, a mixture of 5-Fluoroindole (5.00 g, 5.00 g, 35.5 mmol, 96 mass percent, 1.00) and Maleimide (1.5 equiv., 5.17 g, 53.3 mmol, 1.50) was charged in a 50 mL vessel, and then Acetonitrile (3 L/kg, 15.0 mL, 11.7 g, 286 mmol, 100 mass percent) and Zinc Chloride (1.05 equiv., 5.08 g, 37.3 mmol, 100 mass percent) were added. The reaction was heated to 85° C. over 10 min and then maintained at 85° C. for 24 hrs. While still at 85° C., Water (6 L/kg, 30.0 mL, 30.0 g, 1670 mmol, 100 mass percent) was added slowly, while maintaining the temperature above 80° C. Yellow solids precipitated. The reaction mixture was cooled to 50° C. over 1 hour followed by stirring at 50° C. for 2 hours, then cooled 10° C. over 1 hour. The reaction was stirred at 10° C. for 1 hour. The solids were filtered off, then the filter cake was washed 2 times with 5 ml 1:1 ACN/water to afford isolated compound (6.85 g, 6.85 g, 29.5 mmol, 83.1percent Yield). (0357) For purification, the resulting isolated compound was charged (6.85 g, 6.85 g, 29.5 mmol, 100 mass percent) into a vessel, followed by addition of Tetrahydrofuran (6 L/kg, 41.1 mL, 36.4 g, 505 mmol, 100 mass percent). This mixture was heated to 66° C. to form a homogeneous solution. Heptane (4 L/kg, 27.4 mL, 18.7 g, 187 mmol, 100 mass percent, was added slowly at 66° C.; solids began to precipitate after 5 volumes. The mixture was cooled to 25° C. over 3 hours, then filtered and washed with heptane, followed by drying in the high vacuum oven overnight. Isolated compound (4.93 g, 4.93 g, 21.2 mmol, 100 mass percent, 72.0percent Yield). (0358) This isolated compound is charged 2 (1.00 g, 4.3 mmol, 100 mass percent) into a 50 ml vessel And Tetrahydrofuran (6 L/kg, 6 mL, 100 mass percent) and Heptane (6 L/kg, 6 mL, 100 mass percent) were added. The slurry was stirred at 25° C. for 48 hrs. The solids were filtered off and dried in the high vacuum oven overnight. The Isolated compound: (0.89 g, 0.89 g, 3.83 mmol, 100 mass percent, 89.00percent Yield).
83.1%	Stage #1: With zinc(II) chloride In acetonitrile at 85℃; for 24 h; Microwave irradiation Stage #2: at 10 - 80℃; for 4 h;	Alternatively, a mixture of 5-Fluoroindole (5.00 g, 5.00 g, 35.5 mmol, 96 mass percent, 1.00) and Maleimide (1.5 equiv., 5.17 g, 53.3 mmol, 1.50) was charged in a 50 mL vessel, and then Acetonitrile (3 LIkg, 15.0 mL, 11.7 g, 286 mmol, 100 mass percent) and Zinc Chloride (1.05 equiv., 5.08 g, 37.3 mmol, 100 mass percent) were added. The reaction washeated to 85°C over 10 mm and then maintained at 85°C for 24 hrs. While still at 85°C, Water (6 L/kg, 30.0 mL, 30.0 g, 1670 mmol, 100 mass percent) was added slowly, while maintaining the temperature above 80°C. Yellow solids precipitated. The reaction mixture was cooled to 50°C over 1 hour followed by stirring at 50°C for 2 hours, then cooled 10°C over 1 hour. The reaction was stirred at 10°C for 1 hour. The solids werefiltered off, then the filter cake was washed 2 times with 5 ml 1:1 ACN/water to afford isolated compound (6.85 g, 6.85 g, 29.5 mmol, 83.1percent Yield).For purification, the resulting isolated compound was charged (6.85 g, 6.85 g, 29.5mmol, 100 mass percent) into a vessel, followed by addition of Tetrahydrofuran (6 L/kg, 41.1mL, 36.4 g, 505 mmol, 100 mass percent). This mixture was heated to 66°C to form ahomogeneous solution. Heptane (4 L/kg, 27.4 mL, 18.7 g, 187 mmol, 100 mass percent, wasadded slowly at 66°C; solids began to precipitate after 5 volumes. The mixture wascooled to 25°C over 3 hours, then filtered and washed with heptane, followed by dryingin the high vacuum oven overnight. Isolated compound (4.93 g, 4.93 g, 21.2 mmol, 100mass percent, 72.0percent Yield). This isolated compound is Form 2 shown in FIG. 2.

Reference： [1] Patent: WO2016/181349, 2016, A1, . Location in patent: Page/Page column 26
[2] Patent: US2015/329525, 2015, A1, . Location in patent: Paragraph 0352-0358
[3] Patent: WO2016/181275, 2016, A1, . Location in patent: Page/Page column 20; 21
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9617 - 9629
[5] Tetrahedron, 2005, vol. 61, # 23, p. 5599 - 5614
[6] Patent: WO2016/181348, 2016, A1, . Location in patent: Page/Page column 31-32

[ 541-59-3 ] Synthesis Path-Downstream 1~11

1
[ 541-59-3 ]
[ 2028-85-5 ]
[ 21724-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; copper dichloride; In water; acetone; at 0 - 20℃;pH 3 - 3.5;	Preparation 1: 3-(4-bromophenyl)-1H-pyrrole-2,5-dione (P1) A solution of hydrochloric acid (37percent, 27 ml.) in water (11 ml_) was added to 4-bromo aniline (15 g) at room temperature with vigorous stirring and the formed precipitate was allowed to stir for further 30 minutes. Temperature was reduced to 0 0C and a solution of sodium nitrite (6.60 g) in water (17 ml_) was added dropwise to the stirred suspension. At the end of diazotisation, a clear yellow solution was obtained. Maleimide (16.90 g) in acetone (70 mL) was added dropwise at 0 0C and then the pH of the solution was adjusted to 3-3.5 by adding sodium acetate. Copper (II) chloride (1.76 g) was added to the vigorously stirred mixture. The reaction mixture was allowed to stir at 0 0C for 1 h and overnight at room temperature. Acetone was removed in vacuo, the residue was filtered and dried overnight in vacuo to give the crude title compound (14.12 g) which was used without further purification.MS (mlz): 251 [M-H]".

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2313
[2]Patent: WO2007/22935,2007,A1 .Location in patent: Page/Page column 34

2
[ 541-59-3 ]
[ 557-24-4 ]

Reference： [1]Journal of Pharmaceutical Sciences,1984,vol. 73,p. 1767 - 1771
[2]Bulletin des Societes Chimiques Belges,1937,vol. 46,p. 197

3
[ 541-59-3 ]
[ 57497-39-9 ]
C₈H₁₃N₂O₃ [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 1865 - 1868

4
[ 541-59-3 ]
[ 106-40-1 ]
diazonium salt [ No CAS ]
[ 21724-96-9 ]
[ 101422-55-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2313

5
[ 5926-51-2 ]
[ 20781-20-8 ]
[ 541-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid;	Scheme C-6 illustrates the synthesis of the maleimide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of <strong>[5926-51-2]bromomaleic anhydride</strong> B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78.
	In acetic acid;	Scheme C-6 illustrates the synthesis of the maleimide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of <strong>[5926-51-2]bromomaleic anhydride</strong> B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78.

Reference： [1]Patent: US6423713,2002,B1
[2]Patent: US6514977,2003,B1

6
[ 557-24-4 ]
[ 541-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	COMPARATIVE EXAMPLE 2 The same procedure as in Example 7 was repeated, except that the washed reaction mixture was directly cooled to 30 C. without conducting distillation of toluene. The precipitate thus formed was collected by filtration and dried at 70 C. for 48 hours. There was obtained 67.6 g (apparent yield: 97.2%) of a pale yellow maleimide powder. The resulting maleimide contained 13.1% toluene and 1.8% mono<strong>[557-24-4]maleamic acid</strong>, had a melting point of 140 to 145 C., and exhibited a non-crystallization rate of 0%.
	With sodium acetate; In acetic anhydride;	General Procedure for the Synthesis of N-Substitutedmaleimides and Succmimides. A reaction mixture containing the appropriate <strong>[557-24-4]maleamic acid</strong> (5.23 mmol) in 5 mL of acetic anhydride and sodium acetate (3 mmol) was heated at 90 C. for 2 hours. The reaction was cooled and quenched with water. The aqueous solution was extracted with Et2 O (3*40 mL). The combined ether extracts were dried (Na2 SO4), filtered and the solvent was evaporated. The residue was chromatographed on silica gel with EtOAc/hexane. The fractions containing the pure product were combined and concentrated to afford essentially pure maleimide. The product was further recrystallized from isopropanol/water. In the case of the aspirin analogs 13 and 14 purification on silica gel was not needed as the compounds were crystallized from CHC/3 /hexane.
		The continuously stirred solution of <strong>[557-24-4]maleamic acid</strong> 13 in presence of a nitrogen atmosphere was heated in an oil bath maintained at 150-160 for 1.5 h and then at 170-180 for 1.5 h. The reaction was allowed to cool and then poured over crushed ice. Light gray solid obtained on maceration was filtered, washed with water, and dried to give the maleimide 14, m.p. 152-155 C.

With maleic anhydride; malic acid; In 1-methyl-pyrrolidin-2-one; toluene; at 95℃; for 8.0h;Inert atmosphere;

In a glass reaction vessel, under nitrogen atmosphere, a dimer diamine (manufactured by Croda Japan KK "Preamine 1075", molecular weight: 549): 1.0 mol, a mixture composed of toluene and NMP A solvent (mass ratio: toluene / NMP = 80/20) was added and stirred. Next, to this solution , 2.10 mol of maleic anhydride was added, followed by stirring at 25 C. for 1 hour, To obtain a <strong>[557-24-4]maleamic acid</strong> solution. Thereafter, to this solution, 1.8 mol of maleic acid and 1.8 mol of maleic anhydride were added, While stirring, the liquid temperature was raised to 95 C., the heating was continued for 8 hours while maintaining the same temperature, and then cooled to obtain an orange yellow solution. The solid content concentration in this reaction is, 30% by mass. When the NMR of this solution was measured under the above conditions and the conversion was calculated, The conversion rate was 92% Except for using 1,12-dodecanediamine as the diamine, As a result of carrying out the reaction in the same manner as in Example 3, the conversion was 95%.

Reference： [1]Patent: US5371236,1994,A
[2]Patent: US5475021,1995,A
[3]Patent: US4550177,1985,A
[4]Patent: JP2017/66132,2017,A .Location in patent: Paragraph 0021; 0025

7
[ 7647-01-0 ]
[ 557-24-4 ]
[ 541-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In methanol; chloroform;	This crude <strong>[557-24-4]maleamic acid</strong> was chromatographed on 60 g of 230-400 mesh silica gel, eluding with CHCl3 /25% NH4 OH in MeOH (4:1). After 90 mls of column volume were voided, 3 ml fractions (numbers 38-80) were collected. NMR was consistent with the desired <strong>[557-24-4]maleamic acid</strong> intermediate. 85 mg of this <strong>[557-24-4]maleamic acid</strong> was dissolved in 4 ml of CHCl3. 151 mul of 1.6 mm acetic anhydride was added followed by 46 mg of anhydrous sodium acetate and the mixture was stirred overnight at 20-25. TLC revealed product formation which was worked up by evaporation under reduced pressure to yield crude product. The entire crude was chromatographed on a medium pressure sytem utilizing a 25 g (230-400 mesh) silica gel column, eluted with CH2 Cl2 /10% NH4 OH in MeOH (8:1). The column volume fraction plus fractions numbers 1-8, yielded the title compound. MS (M+H)+: 508.3570 (PLA2)

Reference： [1]Patent: US4917826,1990,A

8
[ 108-31-6 ]
[ 1336-21-6 ]
amine ether steroid 3-[(3-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-yl)oxy]-1-propanamine [ No CAS ]
[ 557-24-4 ]
[ 541-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; chloroform; o-xylene; N,N-dimethyl-formamide;	EXAMPLE 241 1H-Pyrrole-2,5-dione, 1-[3-[(3-melthoxyestra-1,3,5(10)-trien-17-yl)oxy]propyl] 100 mg of the amine ether steroid 3-[(3-methoxyestra-1,3,5(10)-trien-17-yl)oxy]-1-propanamine and 34 mg of maleic anhydride were slurried in 10 ml of o-xylene and refluxed for 1 hour. TLC (CHCl3 /4.2M NH3 in MeOH (12:1)) revealed all starting material gone. After 2 hours total reflux the reaction was stopped and allowed to stand for 2 days. TLC (CHCl3 /25% NH4 OH in MeOH (4:1)) revealed that the maleiamic acid was formed. The reaction mixture was placed on the high vacuum, evaporated under reduced pressure to produce crude product (120 mg). The 120 mg of <strong>[557-24-4]maleamic acid</strong> was slurried in 2 ml of xylene and 1 ml DMF, 9 mg of Amberlyst 15 resin were added and the reaction mixture was heated to reflux. After 3 hours of reflux, TLC (CHCl3 /4.2M NH3 in MeOH (12:1)) revealed no product formation, therefore the mixture was refluxed overnight. TLC in CHCl3 /25% NH4 OH in MeOH (4:1) revealed product formation and that some of the <strong>[557-24-4]maleamic acid</strong> was present. The reaction was cooloed and then was evaporated under reduced pressure under high vacuum to produce crude product (129 mg). The entire crude was chromatographed on 25 g of 230-400 mesh silica gel eluding with 100% CHCl3. After 50 ml (1 column volume) was collected, 2 ml fractions were taken. Fraction numbers 3-9 yielded 10 mg of product. MS C26 H33 NO3: Theory 423.2409, Measured 423.2386. (PLA2)

Reference： [1]Patent: US4917826,1990,A

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 17 Imidization of the Maleamic Acid 30a to the Imide 31a A magnetically stirred DMAC solution of the tetrakismaleamic acid 30a in a nitrogen atmosphere was thermally cyclodehydrated in situ. The heating was performed in an oil bath maintained at 140-145 C. for 1 h and then at 160-165 C. for 1 h. After cooling, the light-brown solution was poured dropwise into continuously stirred cold methanol. The light-yellow solid obtained was macerated with fresh methanol, filtered, and dried to give the desired maleimide 31a (5.8 g).

10
[ 541-59-3 ]
[ 541-41-3 ]
[ 55750-49-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 4-methyl-morpholine; In water; ethyl acetate;	1) Ethyl-2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 9.7 g (0.1 mol) of maleimide are solubilized in 50 ml of ethyl acetate and 1.1 ml of N-methylmorpholine at 5 C. 1.1 ml of ethyl chloroformate are added dropwise. The mixture is stirred for 1/2 hour. The insoluble material is removed by filtration. The filtrate is washed with 50 ml of water. The organic phase is dried over MgSO4 and is then concentrated under vacuum. The oil obtained is purified on Merck Geduran silica gel (40-63 mum). Elution: CH2Cl2/ACOEt 66/34. 16.9 g are isolated with a yield of 50%. Mass spectrum: M/z=170.1 (ES+) theoretical M=169
41%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 4h;	Ethyl chloroformate (0.38 ml, 4 mmol) was added dropwise to a stirred solution maleimide (0.3 g, 3 mmol) and triethylamine (0.5 ml, 3.5 mmol) in dimethylformamide (2 ml) at 0-5 C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3*10 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum. The residue was purified in chloroform and hexane on a silica gel column to give N-ethoxycarbonyl-maleimide (yield 41%). 1H NMR (CDCl3) delta 1.34 (3H, t, CH3), 4.27 (2H, q, CH2), 6.21 (1H, d, CH=), 6.72 (1H, d, CH=).

Reference： [1]Organic Letters,2015,vol. 17,p. 5846 - 5849
[2]Chemical Communications,2014,vol. 50,p. 859 - 861
[3]Patent: US2010/297025,2010,A1
[4]Patent: US9273304,2016,B2 .Location in patent: Page/Page column 16

11
[ 541-59-3 ]
[ 106-40-1 ]
[ 21724-96-9 ]

Yield	Reaction Conditions	Operation in experiment
57%		A solution of hydrochloric acid (37percent, 13 mL) in water (5.5 mL) was added to 4-bromoaniline (7.48 g, 43.52 mmol) at r.t. with vigorous stirring and the formed precipitate was allowed to stir for 30 min. The reaction mixture was cooled to 0 °C and a solution of sodium nitrite (3.30 g, 47.87 mmol) in water (9 mL) was added dropwise. At the end of diazotization, a clear yellow solution was obtained. Maleimide (8.45 g, 87.05 mmol) in acetone (35 mL) was added dropwise at 0 °C and then the pH of the solution was adjusted to 3-3.5 by adding sodium acetate. CuCl2 (0.88 g, 6.57 mmol) was added to the vigorously stirred mixture. The reaction mixture was stirred at 0 °C for Ih and overnight at r.t. After completion of the reaction as confirmed by TLC, solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 4: 6 EtOAc: Pet. ether) to afford the title compound as a yellow solid (5.8 g, 57percent). ESIMS (m/z): 252.3 (M+l)
57%		Step 1: Preparation of 3-(4-bromophenyl)-1H-pyrrole-2,5-dioneA solution of hydrochloric acid (37percent, 13 mL) in water (5.5 mL) was added to 4-bromoaniline (7.48 g, 43.52 mmol) at r.t. with vigorous stirring and the formed precipitate was allowed to stir for 30 min. The reaction mixture was cooled to 0° C. and a solution of sodium nitrite (3.30 g, 47.87 mmol) in water (9 mL) was added dropwise. At the end of diazotization, a clear yellow solution was obtained. Maleimide (8.45 g, 87.05 mmol) in acetone (35 mL) was added dropwise at 0° C. and then the pH of the solution was adjusted to 3-3.5 by adding sodium acetate. CuCl2 (0.88 g, 6.57 mmol) was added to the vigorously stirred mixture. The reaction mixture was stirred at 0° C. for 1 h and overnight at r.t. After completion of the reaction as confirmed by TLC, solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether) to afford the title compound as a yellow solid (5.8 g, 57percent).ESIMS (m/z): 252.3 (M+1)

Reference： [1]RSC Advances,2016,vol. 6,p. 23438 - 23447
[2]Patent: WO2010/150281,2010,A2 .Location in patent: Page/Page column 69
[3]Patent: US2012/165320,2012,A1 .Location in patent: Page/Page column 43-44

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Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? 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 Amines ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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Related Functional Groups of
[ 541-59-3 ]

Amides

[ 930-88-1 ]

1-Methyl-1H-pyrrole-2,5-dione

Similarity: 0.90

[ 4144-22-3 ]

1-(tert-Butyl)-1H-pyrrole-2,5-dione

Similarity: 0.79

[ 952292-18-1 ]

1-(4-Aminobutyl)-1H-pyrrole-2,5-dione hydrochloride

Similarity: 0.76

[ 1187-59-3 ]

N-Methylacrylamide

Similarity: 0.73

[ 54641-27-9 ]

N-(2-Aminoethyl)acrylamide hydrochloride

Similarity: 0.72

Related Parent Nucleus of
[ 541-59-3 ]

Pyrrolines

[ 930-88-1 ]

1-Methyl-1H-pyrrole-2,5-dione

Similarity: 0.90

[ 4144-22-3 ]

1-(tert-Butyl)-1H-pyrrole-2,5-dione

Similarity: 0.79

[ 952292-18-1 ]

1-(4-Aminobutyl)-1H-pyrrole-2,5-dione hydrochloride

Similarity: 0.76

[ 25021-08-3 ]

2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Similarity: 0.68

[ 7423-55-4 ]

3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid

Similarity: 0.65

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. 541-59-3 ] {[proInfo.proName]}

Quality Control of [ 541-59-3 ]

Related Doc. of [ 541-59-3 ]

Product Details of [ 541-59-3 ]

Calculated chemistry of [ 541-59-3 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 541-59-3 ]

Application In Synthesis of [ 541-59-3 ]

[ 541-59-3 ] Synthesis Path-Upstream 1~1

[ 541-59-3 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 541-59-3 ]

Amides

Related Parent Nucleus of [ 541-59-3 ]

Pyrrolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 541-59-3 ]

Related Parent Nucleus of
[ 541-59-3 ]