114438-75-4

Usage

Uses

Used in Organic Synthesis:
(2R)-2-bromo-Butanoic acid methyl ester is used as a reagent in organic synthesis for its ability to undergo nucleophilic substitution, which is crucial in various synthetic processes.
Used in Chemical Reactions:
In the chemical industry, (2R)-2-bromo-Butanoic acid methyl ester is used as a reagent to facilitate specific chemical reactions, taking advantage of its unique bromine atom and carboxylic acid functional group.

Upstream product

• 186581-53-3 diazomethane 
• 80-58-0 2-Bromobutyric acid 
• 3196-15-4 Methyl 2-bromobutyrate 
• 17642-18-1 (E)-α-bromocrotonate de methyle 
• 67-56-1 methanol 
• 2681-94-9 (2R)-2-bromobutanoic acid 

Relevant academic research and scientific papers

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.

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

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.