7425-63-0

Basic information

• Product Name: Methyl Bromopyruvate
• Synonyms: 3-Bromo-2-oxopropionic acid methyl ester;Methyl bromopyruvate ,90%;Methyl broMide acetone;BrCH2COCO2Me;Methyl bromopyruvate, Methyl 3-bromo-2-oxopropionate;Methyl broMopyruvate technical;3-bromo-2-oxoPropanoic acid methyl ester;METHYL BROMOPYRUVATE
• CAS NO: 7425-63-0
• Molecular Formula: C₄H₅BrO₃
• Molecular Weight: 180.98
• Product Categories: C2 to C5;Carbonyl Compounds;Esters
• Mol File: 7425-63-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 5°C(lit.)
• Boiling Point: 84°C/10mmHg(lit.)
• Flash Point: 125 °C
• Appearance: /
• Density: 1.70 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.65mmHg at 25°C
• Refractive Index: n20/D 1.480
• Storage Temp.: 2-8°C
• BRN: 1754888
• CAS DataBase Reference: Methyl Bromopyruvate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl Bromopyruvate(7425-63-0)
• EPA Substance Registry System: Methyl Bromopyruvate(7425-63-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• F: 19
• Hazardous Substances Data: 7425-63-0(Hazardous Substances Data)

Usage

Uses

Methyl bromopyruvate was used in the synthesis of 2-(4-amino-4-carboxybutyl)thiazole-4-carboxylic acid and methyl-1-(bromomethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate.

General Description

Methyl bromopyruvate is an inhibitor of carbonic anhydrase.

InChI:InChI=1/C4H5BrO3/c1-8-4(7)3(6)2-5/h2H2,1H3

Synthetic route

(S)-Methyl lactate (27871-49-4) → methyl 3-bromo-2-oxopropanoate (7425-63-0)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane for 6h; Reflux;	61%

pyruvic acid methyl ester (600-22-6) → methyl 3-bromo-2-oxopropanoate (7425-63-0)

Conditions	Yield
With tetrachloromethane; bromine am Licht;
With pyridine; bromine at 40 - 50℃;
With bromine at 65℃; unter Durchleiten von CO2;

methanol (67-56-1) + bromopyruvic acid (1113-59-3) → methyl 3-bromo-2-oxopropanoate (7425-63-0)

Conditions	Yield
With hydrogenchloride at 20℃; for 15h;
hydrogenchloride In water at 30 - 40℃; for 9h;

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 2-chloro-6-methoxynicotinthioamide → 2-chloro-6-methoxy-3-[4-(methoxycarbonyl)thiazol-2-yl]pyridine

Conditions	Yield
With pyridine In ethanol at 80℃; for 3.5h; Inert atmosphere;	100%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + (R)-tert-butyl 1-amino-3-phenyl-1-thioxopropan-2-ylcarbamate → (R)-methyl 2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazole-4-carboxylate (101924-70-3)

Conditions	Yield
With calcium carbonate In ethanol at 20℃; Hantzsch cyclization; Inert atmosphere;	99%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + thiourea (17356-08-0) → methyl 2-amino-1,3-thiazole-4-carboxylate (118452-04-3)

Conditions	Yield
In methanol for 2h; Hantzsch Thiazole Synthesis; Reflux;	93%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 2,2-diethoxythioacetamide (73956-15-7) → methyl 2-(diethoxymethyl)thiazole-4-carboxylate

Conditions	Yield
In methanol for 1.5h; Molecular sieve; Reflux;	91%
With hydrogenchloride In methanol; water at 65℃; for 3.25h; Molecular sieve;

carbon disulfide (75-15-0) + 2-amino-benzthiazole (136-95-8) + methyl 3-bromo-2-oxopropanoate (7425-63-0) → methyl 3-(benzo[d]thiazol-2-yl)-2-thioxo-2,3-dihydrothiazole-4-carboxylate

Conditions	Yield
In toluene Reflux;	90%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 6-methoxybenzo[d]thiazole-2-carbothioamide (71368-35-9) → 2-(6-methoxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid methyl ester (7775-89-5)

Conditions	Yield
In methanol at 20℃; for 39h; Reflux;	88%
In methanol

methyl 3-bromo-2-oxopropanoate (7425-63-0) + (S)-N-(tert-butoxycarbonyl)-O-(tert-butyldiphenylsilyl)serinethioamide → methyl (S)-2-(1-tert-butoxycarbonylamino-2-tert-butyldiphenylsiloxy)ethylthiazole-4-carboxylate

Conditions	Yield
Stage #1: methyl 3-bromo-2-oxopropanoate; (S)-N-(tert-butoxycarbonyl)-O-(tert-butyldiphenylsilyl)serinethioamide With potassium hydrogencarbonate In 1,2-dimethoxyethane at 0 - 20℃; Stage #2: With 2,6-dimethylpyridine; trifluoroacetic anhydride In 1,2-dimethoxyethane at 0 - 20℃;	88%
Stage #1: methyl 3-bromo-2-oxopropanoate; (S)-N-(tert-butoxycarbonyl)-O-(tert-butyldiphenylsilyl)serinethioamide With potassium hydrogencarbonate In 1,2-dimethoxyethane at 0 - 20℃; for 3h; Stage #2: With 2,6-dimethylpyridine; trifluoroacetic anhydride In 1,2-dimethoxyethane at 0℃; for 1h;	88%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + (R)-3-t-butoxycarbonyl-2,2-dimethylthiazolidine-4-carbothioamide (246265-78-1) → 2',2'-dimethyl-4',5'-dihydro-[2,4']bithiazolyl-4,3'-dicarboxylic acid 3'-tert-butyl ester 4-methyl ester (924288-22-2)

Conditions	Yield
Stage #1: methyl 3-bromo-2-oxopropanoate; (R)-3-t-butoxycarbonyl-2,2-dimethylthiazolidine-4-carbothioamide With potassium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 22h; Inert atmosphere; Stage #2: With pyridine; trifluoroacetic anhydride In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere;	86%
Stage #1: methyl 3-bromo-2-oxopropanoate; (R)-3-t-butoxycarbonyl-2,2-dimethylthiazolidine-4-carbothioamide With potassium hydrogencarbonate In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: With pyridine; trifluoroacetic anhydride In tetrahydrofuran Cooling with ice;	79%
Stage #1: methyl 3-bromo-2-oxopropanoate; (R)-3-t-butoxycarbonyl-2,2-dimethylthiazolidine-4-carbothioamide With potassium hydrogencarbonate In tetrahydrofuran at 20℃; Stage #2: With pyridine; trifluoroacetic anhydride In ethyl acetate Cooling with ice;

5-bromo-3-(trifluoromethyl)pyridin-2-amine (79456-34-1) + methyl 3-bromo-2-oxopropanoate (7425-63-0) → 6-Bromo-8-trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid methyl ester (1121058-16-9)

Conditions	Yield
at 50℃; for 3h;	82%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 3-trifluoromethyl-1,2-dihydro-pyridin-2-ylamine (1379165-19-1) → 8-trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid methyl ester (1206972-73-7)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	80%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + tryptamine hydochloride (343-94-2) → methyl 1-(bromomethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate (1189356-88-4)

Conditions	Yield
With pyrographite In methanol for 18h; Pictet-Spengler condensation; Reflux; Inert atmosphere;	78%
In methanol at 80℃;

6-hydroxybenzothiazole-2-thiocarboxamide (36727-08-9) + methyl 3-bromo-2-oxopropanoate (7425-63-0) → dehydroluciferin methyl ester (36727-10-3)

Conditions	Yield
In methanol 1.) 25 deg C, 21 h, 2.) reflux, 1.3 h;	77%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + benzenecarbothioamide (2227-79-4) → 2-phenyl-1,3-thiazole-4-carboxylic acid methyl ester (7113-02-2)

Conditions	Yield
In tetrahydrofuran for 18h; Reflux;	77%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + urea (57-13-6) → C5H6N2O3 (1000576-38-4)

Conditions	Yield
In ethanol at 90℃;	75%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + C13H22N2O4S → C17H24N2O6S

Conditions	Yield
Stage #1: methyl 3-bromo-2-oxopropanoate; C13H22N2O4S With potassium hydrogencarbonate In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: With pyridine; trifluoroacetic anhydride In tetrahydrofuran Cooling with ice;	75%
Stage #1: methyl 3-bromo-2-oxopropanoate; C13H22N2O4S With potassium hydrogencarbonate In tetrahydrofuran at 20℃; Stage #2: With pyridine; trifluoroacetic anhydride In ethyl acetate Cooling with ice;

N-tert-butoxycarbonyl-O-(4-methoxybenzyl)thiothreoninamide + methyl 3-bromo-2-oxopropanoate (7425-63-0) → methyl 2-[(S)-1-(tert-butoxycarbonylamino)-(R)-2-(4-methoxybenzyl)propyl]thiazole-4-carboxylate

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-O-(4-methoxybenzyl)thiothreoninamide; methyl 3-bromo-2-oxopropanoate With potassium hydrogencarbonate In 1,2-dimethoxyethane at 0℃; for 1h; Hantzsch reaction; Stage #2: With 2,6-dimethylpyridine; trifluoroacetic anhydride In 1,2-dimethoxyethane at 0℃; for 2h; Further stages.;	74%

pyridine (110-86-1) + methyl 3-bromo-2-oxopropanoate (7425-63-0) + 3-cyclohexylimino-2-(diisopropoxy-phosphoryloxy)-acrylic acid ethyl ester (1146344-31-1) → C19H24N2O4 (1259393-58-2)

Conditions	Yield
Stage #1: pyridine; methyl 3-bromo-2-oxopropanoate In acetonitrile at 60℃; for 0.5h; Stage #2: 3-cyclohexylimino-2-(diisopropoxy-phosphoryloxy)-acrylic acid ethyl ester With potassium carbonate In acetonitrile at 20℃;	74%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 3-amino-4-bromo-6-(4-fluorophenyl)pyridazine (1421637-26-4) → methyl 8-bromo-6-(4-fluorophenyl)imidazo[1,2-b]pyridazine-2-carboxylate

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 17h;	73%
In N,N-dimethyl-formamide at 75℃; for 4h; Temperature;	19.9 g

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 8-trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid methyl ester (1206972-73-7)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 3h;	72%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 6-chloro-4-isopropenylpyridazin-3-amine → methyl 6-chloro-8-isopropenylimidazo[1,2-b]pyridazine-2-carboxylate

Conditions	Yield
In N,N-dimethyl-formamide at 75℃; for 3h;	72%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + acetoacetic acid methyl ester (105-45-3) → dimethyl 2-methylfuran-3,4-dicarboxylate (6141-60-2)

Conditions	Yield
at 50℃; Feist-Benary Furan Synthesis;	72%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + tert-butyl (S)-(1-amino-1-thioxopropan-2-yl)carbamate (141041-86-3, 96929-01-0, 140903-30-6) → methyl (S)-2-[1-(tert-butoxycarbonylamino)ethyl]thiazole-4-carboxylate

Conditions	Yield
Stage #1: methyl 3-bromo-2-oxopropanoate; tert-butyl (S)-(1-amino-1-thioxopropan-2-yl)carbamate With potassium hydrogencarbonate In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: With pyridine; trifluoroacetic anhydride In tetrahydrofuran Cooling with ice;	72%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 6-chloro-4-(trifluoromethyl)pyridazin-3-amine (1610008-47-3) → methyl 6-chloro-8-(trifluoromethyl)imidazo[1,2-b]pyridazine-2-carboxylate

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 5h;	70%

6-chloro-pyridazin-3-ylamine (5469-69-2) + methyl 3-bromo-2-oxopropanoate (7425-63-0) → methyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylate

Conditions	Yield
In N,N-dimethyl acetamide at 50℃; for 1.5h; Inert atmosphere;	65.66%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + thioacetamide (62-55-5) → methyl 2-methyl-1,3-thiazole-4-carboxylate (6436-60-8)

Conditions	Yield
In methanol at 20℃; Inert atmosphere; Heating;	65%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 2-aminobenzothioamide (2454-39-9) → methyl 2-(2-aminophenyl)thiazole-4-carboxylate

Conditions	Yield
In N,N-dimethyl-formamide at 65℃; for 2h; Inert atmosphere;	65%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + thiophenol (108-98-5) → Methyl 2-oxo-3-phenylthiopropionate (115413-26-8)

Conditions	Yield
With pyridine In diethyl ether at 0 - 5℃; for 0.5h;	64%

4-bromo-6-chloro-3-pyridazineamine (446273-59-2) + methyl 3-bromo-2-oxopropanoate (7425-63-0) → methyl 8-bromo-6-chloroimidazo[1,2-b]pyridazine-2-carboxylate

Conditions	Yield
In N,N-dimethyl acetamide; N,N-dimethyl-formamide at 70℃; for 18h;	62%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + N1-(1-methyl-1H-pyrazol-5-yl)benzene-1,2-diamine → methyl 4-(bromomethyl)-1-methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine-4-carboxylate

Conditions	Yield
With trifluoroacetic acid In acetonitrile at 20℃; for 12h; Pictet-Spengler Synthesis;	61%

Upstream product

• 67-56-1 methanol 
• 1113-59-3 bromopyruvic acid 
• 27871-49-4 (S)-Methyl lactate 
• 600-22-6 pyruvic acid methyl ester 

Downstream Products

• 62235-61-4 2-bromomethyl-3-oxo-3,4-dihydroquinoxaline 
• 92868-78-5 dimethyl 2,2′-(1,4-phenylene)dithiazole-4-carboxylate 
• 115413-26-8 Methyl 2-oxo-3-phenylthiopropionate 
• 6436-60-8 methyl 2-methyl-1,3-thiazole-4-carboxylate 
• 1000576-38-4 C₅H₆N₂O₃ 
• 448906-42-1 ITE 
• 6141-60-2 dimethyl 2-methylfuran-3,4-dicarboxylate 
• 572910-59-9 methyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylate 
• 7113-02-2 2-phenyl-1,3-thiazole-4-carboxylic acid methyl ester 
• 1206981-34-1 methyl 8-chloroimidazo[1,2-a]pyrazine-2-carboxylate 
• 1315324-53-8 methyl 2-((2S)-1-((2S,4R)-2-((2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl-carbamoyl)-4-(2-(4-(trifluoromethyl)phenyl)benzofuro[3,2-d]pyrimidin-4-yloxy-)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylamino)thiazole-4-carboxylate 

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