70288-61-8

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-BROMOHEXANOATE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new medications and enhance the properties of existing ones.
Used in Flavor and Fragrance Industry:
METHYL 2-BROMOHEXANOATE is used as a building block in the production of flavoring agents and fragrances, capitalizing on its fruity odor to create desirable scents and tastes.
Used in Organic Synthesis:
METHYL 2-BROMOHEXANOATE is used as a reagent in organic synthesis, playing a crucial role in the formation of more complex chemical compounds for various applications.

InChI:InChI=1/C7H13BrO2/c1-3-4-5-6(8)7(9)10-2/h6H,3-5H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 91423-84-6 (2S)-2-bromohexanoic acid 
• 186581-53-3 diazomethane 
• 616-05-7 2-bromohexanoic acid 
• 5445-19-2 methyl 2-bromohexanoate 
• 13894-63-8 methyl (E)-hex-2-enoate 
• 931382-07-9 C₇H₁₁BrO₂ 
• 931382-06-8 C₇H₁₁BrO₂ 

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.

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.