69043-96-5

Basic information

• Product Name: METHYL 2-BROMOBUTYRATE
• Synonyms: DL-METHYL 2-BROMOBUTYRATE;METHYL 2-BROMO-N-BUTYRATE;METHYL 2-BROMOBUTANOATE;ALPHA-BROMOBUTYRIC ACID METHYL ESTER;2-BROMO-N-BUTYRIC ACID METHYL ESTER;Butanoic acid, 2-bromo-, methyl ester;Einecs 221-699-0;Nsc 21974
• CAS NO: 69043-96-5
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• EINECS: 221-699-0
• Product Categories: ACID BASED BROMO COMPOUNDS
• Mol File: 69043-96-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 137-138 °C50 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Liquid
• Density: 1.573 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.452(lit.)
• CAS DataBase Reference: METHYL 2-BROMOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-BROMOBUTYRATE(69043-96-5)
• EPA Substance Registry System: METHYL 2-BROMOBUTYRATE(69043-96-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• F: 19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 69043-96-5(Hazardous Substances Data)

Usage

General Description

Methyl 2-Bromobutyrate is a chemical compound often used in the synthesis of various pharmaceuticals and organic compounds. Its molecular formula is C5H9BrO2 and it is also referred to as 2-Bromobutyric acid methyl ester. This colorless liquid possesses a fruity, spicy scent and is typically packaged under nitrogen. Methyl 2-Bromobutyrate is not classified as hazardous, but should be handled with care due to its potential for skin and eye irritation on contact, and respiratory irritation if inhaled. It should be stored in a cool, dry and well-ventilated area away from incompatible substances such as oxidizing agents, bases, and heat sources.

Upstream product

• 141-75-3 butyryl chloride 
• 67-56-1 methanol 
• 107-92-6 butyric acid 
• 22118-12-3 2-bromobutanoyl chloride 
• 186581-53-3 diazomethane 
• 80-58-0 2-Bromobutyric acid 
• 3196-15-4 Methyl 2-bromobutyrate 
• 17642-18-1 (E)-α-bromocrotonate de methyle 
• 2681-94-9 (2R)-2-bromobutanoic acid 

Downstream Products

• 99972-21-1 2-pentachlorophenoxy-butyric acid methyl ester 
• 68039-27-0 methyl 2-ethyl-3-oxohexanoate 
• 90794-35-7 2-(2-iodo-phenoxy)-butyric acid 
• 90794-36-8 2-(4-iodo-phenoxy)-butyric acid 
• 90888-05-4 2-(3-Iod-phenoxy)-buttersaeure 
• 554-24-5 2-(2,4,6-triiodo-phenoxy)-butyric acid 
• 91349-85-8 2-(3,5-diiodo-4-methoxy-phenoxy)-butyric acid 
• 90917-53-6 2-(3,5-diiodo-phenoxy)-butyric acid 
• 90917-51-4 2-(2,5-diiodo-phenoxy)-butyric acid 
• 90917-52-5 2-(3,4-diiodo-phenoxy)-butyric acid 
• 90842-74-3 2-(3,4,5-triiodo-phenoxy)-butyric acid 
• 91349-84-7 2-(3,5-diiodo-2-methoxy-phenoxy)-butyric acid 
• 90800-03-6 2-(3,6-dichloro-2,4-diiodo-phenoxy)-butyric acid 
• 13794-14-4 2-phenoxybutyric acid 

Relevant articles and documents

GC separation of enantiomers of alkyl esters of 2-bromo substituted carboxylic acids enantiomers on 6-tbdms-2,3-di-alkyl- β- And γ-cyclodextrin stationary phases

The gas chromatographic separation of enantiomers of 2-Br carboxylic acid derivatives was studied on four different 6-TBDMS-2,3-di-O-alkyl- β- and -γ-CD stationary phases. The differences in thermodynamic data {ΔH and -ΔS} for the 15 structurally related

Enoate reductase-mediated preparation of methyl (S)-2-bromobutanoate, a useful key intermediate for the synthesis of chiral active pharmaceutical ingredients

Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of α-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.

Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar = 4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to α-bromoesters 9 with minimal racemisation, α-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.