3196-15-4

Basic information

• Product Name: 2-Bromobutyric acid methyl ester
• Synonyms: 2-BROMOBUTYRIC ACID METHYL ESTER;2-BROMO-N-BUTYRIC ACID METHYL ESTER;Methyl-2-bromo butryrate;2-Bromomethylbutyrate;METHYL 2-BROMOBUTYRATE, 1X1ML, MTBE, &;Methyl2-bromobutyrate,97%;(R,S)-2-Bromo-butyric acid methyl ester;2-bromo-butanoic acid methyl ester
• CAS NO: 3196-15-4
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• EINECS: 221-699-0
• Product Categories: 500 Series Drinking Water Methods;EPA;Method 552;C2 to C5;Carbonyl Compounds;Esters;ester series
• Mol File: 3196-15-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 116 °C
• Boiling Point: 137-138 °C50 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: clear slightly yellow liquid
• Density: 1.573 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.43mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in alcohol and ether, slightly soluble in water.
• BRN: 1720826
• CAS DataBase Reference: 2-Bromobutyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobutyric acid methyl ester(3196-15-4)
• EPA Substance Registry System: 2-Bromobutyric acid methyl ester(3196-15-4)

Safety Data

• Hazard Codes: C,Xi,F
• Statements: 34-38-11
• Safety Statements: 26-36/37/39-45-24-16-9
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3196-15-4(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow liquid

Uses

Different sources of media describe the Uses of 3196-15-4 differently. You can refer to the following data:
1. Methyl 2-bromobutyrate is used in the synthesis of racemic indene ester via Reformatsky reaction with 5-methoxy-1-indanone. (E)-2-methoxymethylene-butyric acid methyl ester via reformatsky reaction with α,α-dichloromethyl methyl ether in the presence of zinc dust.
2. Methyl 2-bromobutyrate has been employed as reagent in the synthesis of: racemic indene ester via Reformatsky reaction with 5-methoxy-1-indanone(E)-2-methoxymethylene-butyric acid methyl ester via Reformatsky reaction with α,α-dichloromethyl methyl ether in the presence of zinc dust(E)-2-methoxymethylene-butyryl chloride

InChI:InChI=1/C5H9BrO2/c1-3-4(6)5(7)8-2/h4H,3H2,1-2H3/t4-/m1/s1

Upstream product

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

Downstream Products

• 13794-14-4 2-phenoxybutyric acid 
• 100942-47-0 Methyl 2-(phenylthio)butanoate 
• 6508-07-2 2-(2.4.6-Trichlorphenoxy)-buttersaeure-methylester 
• 186258-88-8 2-[(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-pent-4-enyl-[1,3]dioxan-5-yloxy]-butyric acid methyl ester 
• 186258-87-7 2-[(2R,4S,5R)-4-But-3-enyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-butyric acid methyl ester 
• 195526-30-8 7-bromo-2-ethyl-4-methyl-benzo[f][1,4]oxazepine-3,5-dione 
• 195526-01-3 2-(2,4-diiodo-6-methylcarbamoyl-phenoxy)-butyric acid methyl ester 
• 195525-99-6 2-(2,4-dibromo-6-methylcarbamoyl-phenoxy)-butyric acid methyl ester 
• 107-01-7 butene-2 
• 874479-85-3 C₅₃H₅₂O₁₆S 
• 653563-74-7 methyl 2-(4-(benzyloxy)phenoxy)butanoate 
• 959416-84-3 methyl 2-(2-formyl-6-methoxy-4-nitrophenoxy)butanoate 
• 6098-56-2 2-Keto-buttersaeure-methylester-2.4-dinitro-phenylhydrazon 
• 1242053-82-2 C₂₂H₂₁NO₄ 

Relevant articles and documents

Cobalt-bisoxazoline-catalyzed asymmetric kumada cross-coupling of racemic α-bromo esters with aryl grignard reagents

The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt-bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone.

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.