609-12-1

Basic information

• Product Name: Ethyl 2-bromo-3-methylbutyrate
• Synonyms: TIMTEC-BB SBB005789;2-bromo-3-methyl-butanoicaciethylester;2-Bromoisovatericacidethylester;alpha-Bromoisovaleric acid ethyl ester;Butyric acid, 2-bromo-3-methyl-, ethyl ester;Ethyl 2-bromo-3-methylbutanoate;2-BROMOISOVALERIC ACID ETHYL ESTER;2-BROMOISOVALERIANIC ACID ETHYL ESTER
• CAS NO: 609-12-1
• Molecular Formula: C₇H₁₃BrO₂
• Molecular Weight: 209.08
• EINECS: 210-178-3
• Product Categories: Pharmaceutical Intermediates;Miscellaneous
• Mol File: 609-12-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 77 °C (12 mmHg)
• Flash Point: 65 °C
• Appearance: Dark gray/Powder, Crystals or Flakes
• Density: 1,276 g/cm3
• Vapor Pressure: 0.751mmHg at 25°C
• Refractive Index: 1.4485-1.4505
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Hexane (Slightly)
• BRN: 1099039
• CAS DataBase Reference: Ethyl 2-bromo-3-methylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-bromo-3-methylbutyrate(609-12-1)
• EPA Substance Registry System: Ethyl 2-bromo-3-methylbutyrate(609-12-1)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34-22-2017/8/20
• Safety Statements: 24/25-45-36/37/39-26
• RIDADR: 3265
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 609-12-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Ethyl 2-Bromoisovalerate (cas# 609-12-1) is a compound useful in organic synthesis.

InChI:InChI=1/C7H13BrO2/c1-4-10-7(9)6(8)5(2)3/h5-6H,4H2,1-3H3/t6-/m0/s1

Synthetic route

ethanol (64-17-5) + 2-bromoisovaleric acid (10323-40-7, 565-74-2) → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
With sulfuric acid for 16h; Reflux;	92%
With sulfuric acid for 2h; Heating;	81%
With sulfuric acid In benzene for 48h; Heating;	80%
With sulfuric acid for 36h; Heating / reflux;	55%
With sulfuric acid

2-bromo-3-methyl-butyryl bromide (26464-05-1) + ethanol (64-17-5) → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
at 60℃; for 1h;	62%
at 80℃;

3-methylbutyric acid (503-74-2) + ethanol (64-17-5) → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
(i) SOCl2, (ii) Br2, I2, (iii) /BRN= 1718733/; Multistep reaction;
(i) SOCl2, (ii) Br2, (iii) /BRN= 1718733/; Multistep reaction;

Ethyl isovalerate (108-64-5) → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
(i) cyclohexyl-isopropyl-amine <li salt="">, THF, (ii) Br2</li>; Multistep reaction;

potassium salt of isopropylmalonic acid monoethyl ester → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
With tetrachloromethane; bromine Destillation des Reaktionsprodukts unter vermindertem Druck;

tetrachloromethane (56-23-5) + bromine (7726-95-6) + potassium 2-(ethoxycarbonyl)-3-methylbutanoate → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
Destillieren des Reaktionsprodukts unter vermindertem Druck;

1,1-Dichloro-3-methyl-1-butene (32363-91-0) → ethyl 2-bromoisovalerate (609-12-1)

Conditions	Yield
With methanesulfonic acid; bromine; chlorine In ethanol

ethyl 2-bromoisovalerate (609-12-1) + phenylacetonitrile (140-29-4) → ethyl 2-isopropyl-3-oxo-4-phenylbutanoate (176519-53-2)

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: phenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	100%
With zinc In tetrahydrofuran for 0.166667h; Heating;	92%
With iodine; zinc In tetrahydrofuran Inert atmosphere;	90%

ethyl 2-bromoisovalerate (609-12-1) + 3,5-dimethylphenylacetonitrile (39101-54-7) → ethyl 4-(3,5-dimethylphenyl)-2-isopropyl-3-oxobutanoate (210645-97-9)

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: 3,5-dimethylphenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	100%
Stage #1: ethyl 2-bromoisovalerate; 3,5-dimethylphenylacetonitrile With zinc In tetrahydrofuran for 1h; Heating / reflux; Stage #2: With potassium carbonate In water for 0.75h; Stage #3: With hydrogenchloride In water for 0.75h;	52%
With hydrogenchloride; zinc 1.) THF; Multistep reaction;
Stage #1: ethyl 2-bromoisovalerate; 3,5-dimethylphenylacetonitrile With iodine; zinc In tetrahydrofuran for 0.5h; Addition; reduction; Heating; Stage #2: With potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Hydrolysis; Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 0.5h; Hydrolysis;
Stage #1: ethyl 2-bromoisovalerate; 3,5-dimethylphenylacetonitrile With zinc In tetrahydrofuran Stage #2: With hydrogenchloride

ethyl 2-bromoisovalerate (609-12-1) + 4-Methoxybenzenethiol (696-63-9) → 2-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid ethyl ester (212768-71-3)

Conditions	Yield
With potassium carbonate In acetone for 8h; Heating;	99%
	99%
	99%
	99%
	99%

ethyl 2-bromoisovalerate (609-12-1) + 4-sulfanylphenol (637-89-8) → ethyl isopropyl [4-(hydroxyphenyl)sulfanyl]acetate (287393-36-6)

Conditions	Yield
	99%
With triethylamine In chloroform at 20℃;

ethyl 2-bromoisovalerate (609-12-1) + 4-Methoxybenzenethiol (696-63-9) + 2-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid ethyl ester (212768-71-3) → N-hydroxy-2-(4-methoxy-phenylsulfanyl)-3-methyl-butyramide

Conditions	Yield
	99%

ethyl 2-bromoisovalerate (609-12-1) + benzenesulfonamide (98-10-2) → 2-bromo-3-methyl-N-(phenylsulfonyl)butanamide

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate; benzenesulfonamide In toluene at 50℃; for 0.166667h; Sealed tube; Stage #2: With titanium tetrachloride In toluene at 115℃; for 8h; Solvent; Reagent/catalyst; Sealed tube;	98%

ethyl 2-bromoisovalerate (609-12-1) + 3,5-dimethoxyphenylacetonitrile (13388-75-5) → ethyl 4-(3,5-dimethoxyphenyl)-2-isopropyl-3-oxobutyrate

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate With zinc In tetrahydrofuran for 0.166667h; Reflux; Stage #2: 3,5-dimethoxyphenylacetonitrile In tetrahydrofuran for 0.5h; Reflux;	94%

ethyl 2-bromoisovalerate (609-12-1) → 2-iodo-3-methyl-butyric acid ethyl ester (33666-91-0)

Conditions	Yield
With sodium iodide In acetone Heating / reflux;	93%
With sodium iodide In acetone Heating / reflux;	93%
With sodium iodide In acetone Heating / reflux;	93%

ethyl 2-bromoisovalerate (609-12-1) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → ethyl 3-methyl-2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;	93%
With caesium carbonate In acetonitrile for 4h; Reflux;	79%

ethyl 2-bromoisovalerate (609-12-1) + 1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) → 2-(2-Acetyl-5-methoxy-phenoxy)-3-methyl-butyric acid ethyl ester (176642-59-4)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide Ambient temperature;	91%

ethyl 2-bromoisovalerate (609-12-1) → ethyl 2,2-dibromo-3-methylbutanoate (404392-16-1)

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: With 1,2-dibromo-1,1,2,2-tetrafluoroethane In tetrahydrofuran; hexane at -78℃; for 0.5h;	91%

ethyl 2-bromoisovalerate (609-12-1) + 4-bromobenzyl mercaptan (19552-10-4) → (4-bromophen-yl-4-methylsulfanyl)-3-methylbutanoic acid ethyl ester (796739-75-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 0℃; for 2h;	90%

ethyl 2-bromoisovalerate (609-12-1) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 2-(3,4-Dihydro-naphthalen-1-yl)-3-methyl-butyric acid ethyl ester (143837-09-6)

Conditions	Yield
With zinc	89%
With hydrogen cation; zinc	82%

ethyl 2-bromoisovalerate (609-12-1) + 4-fluorophenylacetonitrile (459-22-3) → ethyl 4-(4-fluorophenyl)-2-isopropyl-3-oxobutanoate (1254831-88-3)

Conditions	Yield
With iodine; zinc In tetrahydrofuran Inert atmosphere;	89%

ethyl 2-bromoisovalerate (609-12-1) + naphthalen-2-ylamine (91-59-8) → (RS)-ethyl α-N-(2-naphthyl)valinate (99631-76-2)

Conditions	Yield
With sodium carbonate at 140℃; for 2h;	88%

ethyl 2-bromoisovalerate (609-12-1) + Hexanethiol (111-31-9) → ethyl 2-hexylsulfanyl-3-methyl-butanoate (1137737-29-1)

Conditions	Yield
With potassium carbonate In acetone for 4h; Reflux;	88%

2-(2-methyl-1,3-dioxolane-2-yl)ethan-1-amine (62240-37-3) + ethyl 2-bromoisovalerate (609-12-1) → (2-(2-methyl-1,3-dioxolan-2-yl)ethyl)valine ethyl ester

Conditions	Yield
With triethylamine In ethyl acetate; acetonitrile at 20℃;	87.8%
With triethylamine In ethyl acetate; acetonitrile at 20℃;	87.8%

2-(2-methyl-1,3-dioxolane-2-yl)ethan-1-amine (62240-37-3) + ethyl 2-bromoisovalerate (609-12-1) → (2-(2-methyl-1,3-dioxolane-2-yl)ethyl)valine ethyl ester

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	87.8%
With triethylamine In acetonitrile at 20℃;	87.8%
With triethylamine In acetonitrile at 20℃;	87.8%

ethyl 2-bromoisovalerate (609-12-1) + 2-butyl-1-[(3'-hydroxybiphenyl-4-yl)methyl]-4-spirocyclohexyl-1H-imidazol-5(4H)-one → 2-butyl-1-[(3'-((1-ethoxycarbonyl-1-(1,1-dimethylmethyl)-methyl)oxy)biphenyl-4-yl)methyl]-4-spirocyclohexyl-1H-imidazol-5(4H)-one

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	87.2%

ethyl 2-bromoisovalerate (609-12-1) + 1-((1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-yl)thiourea (1191465-55-0) → 2-((1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-ylamino)-5-isopropylthiazol-4(5H)-one (1334758-82-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 150℃; for 1h; Microwave irradiation;	87%

1-benzofurane (271-89-6) + ethyl 2-bromoisovalerate (609-12-1) → C15H18O3

Conditions	Yield
With 2,4,6-trimethyl-pyridine; copper(l) iodide; tris[(2-pyridylmethyl)amine] In 1,4-dioxane at 110℃; for 48h;	87%

ethyl 2-bromoisovalerate (609-12-1) + 1-(methyl)-thiourea (598-52-7) → 5-isopropyl-2-(methylamino)-1,3-thiazol-4(5H)-one

Conditions	Yield
With sodium methylate In methanol Reflux;	86%

ethyl 2-bromoisovalerate (609-12-1) + 2-Hydroxybenzophenone (117-99-7) → 2-(2-Benzoyl-phenoxy)-3-methyl-butyric acid ethyl ester

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 70℃; for 3h;	82%

ethyl 2-bromoisovalerate (609-12-1) + p-nitrobenzenesulfonamide (6325-93-5) → 2-bromo-3-methyl-N-[(4-nitrophenyl)sulfonyl]butanamide

Conditions	Yield
Stage #1: ethyl 2-bromoisovalerate; p-nitrobenzenesulfonamide In toluene at 50℃; for 0.166667h; Sealed tube; Stage #2: With titanium tetrachloride In toluene at 115℃; for 24h; Solvent; Sealed tube;	82%

ethyl 2-bromoisovalerate (609-12-1) + 5-(1-(2-chlorobenzene)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazole-2-mercaptan → ethyl 2-(5-(1-(2-chlorobenzyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazole-2-thioether)-3-methylbutyrate

Conditions	Yield
With sodium hydroxide; monophenylthiourea In water; toluene at 80℃; for 5h;	81.7%

ethyl 2-bromoisovalerate (609-12-1) + potassium ethyl xanthogenate (140-89-6) → 2-Ethoxythiocarbonylsulfanyl-3-methyl-butyric acid ethyl ester

Conditions	Yield
In acetone 1.) 1 h, room temperature, 2.) 2 h, 50 deg C, 3.) overnight;	81%

ethyl 2-bromoisovalerate (609-12-1) → dl-2-bromo-3-methyl-1-butanol (84984-06-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h;	80%
With lithium aluminium tetrahydride; diethyl ether

ethyl 2-bromoisovalerate (609-12-1) + 1-(3-phenylisoquinolin-1-yl)thiosemicarbazide (1214257-75-6) → C28H32N4O3S (1214258-01-1)

Conditions	Yield
With sodium acetate In ethanol for 8h; Reflux;	80%

ethyl 2-bromoisovalerate (609-12-1) + (4-fluorophenyl)(1H-pyrrol-2-yl)methanone (13169-73-8) → ethyl 2-{2-[(4-fluorophenyl)carbonyl]-1H-pyrrol-1-yl}-3-methylbutanoate (1528751-84-9)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	80%

Upstream product

• 503-74-2 3-methylbutyric acid 
• 64-17-5 ethanol 
• 10323-40-7 2-bromoisovaleric acid 
• 26464-05-1 2-bromo-3-methyl-butyryl bromide 
• 108-64-5 Ethyl isovalerate 
• 32363-91-0 1,1-Dichloro-3-methyl-1-butene 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 

Downstream Products

• 858492-12-3 α-(toluene-4-sulfonyl)-isobutyric acid ethyl ester 
• 21883-61-4 2-phenylamino-3-methylbutanoic acid 
• 90921-53-2 2,2-dimethyl-3-oxo-2,3-dihydro-4H-1,4-benzothiazine 
• 137514-34-2 Ethyl 2-(2-acetylphenoxy)-3-methylbutanoate 
• 176519-53-2 ethyl 2-isopropyl-3-oxo-4-phenylbutanoate 
• 609-12-1 (S)-ethyl 2-bromoisovalerate 
• 91007-67-9 Meso-α,α'Diisopropyl-Bernsteinsaeure 
• 108-64-5 Ethyl isovalerate 
• 91007-67-9 (+/-)-2,3-Diisopropyl-bernsteinsaeure 
• 148515-21-3 ethyl 2-(diethoxyphosphoryl)-3-methylbutyrate 
• 149950-60-7 Emivirine 
• 176519-55-4 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 21474-92-0 2-Formyl-3-methylbuttersaeure-ethylester 

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