20047-41-0

Basic information

• Product Name: [R,(+)]-2-Bromopropanoic acid methyl ester
• Synonyms: [R,(+)]-2-Bromopropanoic acid methyl ester;[R,(+)]-2-Bromopropionic acid methyl ester
• CAS NO: 20047-41-0
• Molecular Formula: C₄H₇BrO₂
• Molecular Weight: 167
• Mol File: 20047-41-0.mol

Chemical Properties

• Boiling Point: 145.9±8.0 °C(Predicted)
• Appearance: /
• Density: 1.496±0.06 g/cm3(Predicted)
• CAS DataBase Reference: [R,(+)]-2-Bromopropanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [R,(+)]-2-Bromopropanoic acid methyl ester(20047-41-0)
• EPA Substance Registry System: [R,(+)]-2-Bromopropanoic acid methyl ester(20047-41-0)

Safety Data

• Hazardous Substances Data: 20047-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
[R,(+)]-2-Bromopropanoic acid methyl ester is used as an intermediate in the pharmaceutical industry for the synthesis of a wide range of pharmaceuticals. Its versatile chemical structure allows for the creation of diverse medicinal compounds, contributing to the development of new treatments and therapies.
Used in Chemical Synthesis:
In the chemical industry, [R,(+)]-2-Bromopropanoic acid methyl ester serves as a building block for the preparation of various organic compounds. Its reactivity and structural properties make it a valuable component in the synthesis of specialty chemicals and materials.
Used as a Reagent in Chemical Reactions:
[R,(+)]-2-Bromopropanoic acid methyl ester is also utilized as a reagent in chemical reactions, facilitating specific transformations and providing a means to obtain desired products with greater efficiency and selectivity.
Used as a Solvent in Laboratory Applications:
Due to its solubility properties, [R,(+)]-2-Bromopropanoic acid methyl ester is employed as a solvent in various laboratory applications. It aids in the dissolution of certain substances and can be used in the performance of chemical analyses and experiments.
It is crucial to note that the handling and storage of [R,(+)]-2-Bromopropanoic acid methyl ester require caution due to its flammability and potential health hazards, ensuring the safety of both individuals and the environment.

Upstream product

• 67-56-1 methanol 
• 32644-15-8 (S)-2-bromopropanoic acid 
• 7148-74-5 (S)-2-bromopropionyl chloride 
• 17392-83-5 (R)-Methyl lactate 
• 5445-17-0 Methyl 2-bromopropionate 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 186581-53-3 diazomethane 
• 590-92-1 3-Bromopropionic acid 

Downstream Products

• 54656-63-2 methyl (2R)-2-methoxypropanoate 
• 74254-54-9 (-)-(S)-methyl 3,3-bis(benzyloxycarbonyl)-2-methylvalerate 
• 115880-50-7 (R)-2-phenoxypropanoic acid methyl ester 
• 153545-97-2 (R)-(+)-2-(4-methylphenoxy)propanoate 
• 99210-92-1 (R)-2-(4-chlorophenoxy)propanoic acid methyl ester 
• 140146-14-1 (R)-methyl 2-(3-chlorophenoxy) propionate 
• 153546-07-7 methyl (R)-2-(3-nitrophenoxy)propionate 
• 140146-13-0 (R)-methyl 2-(2-chlorophenoxy) propionate 
• 153472-86-7 (R)-methyl 2-(4-phenoxyphenoxy)propanoate 

Relevant articles and documents

USE OF PYRAZOLOPYRIMIDINE DERIVATIVES FOR THE TREATMENT OF PI3K-DELTA RELATED DISORDERS

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HETEROCYCLYLAMINES AS PI3K INHIBITORS

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Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction

The development of efficient methods for the asymmetric Mukaiyama aldol reaction in aqueous solution has received great attention. We have developed a new series of chiral lanthanide-containing complexes that produce Mukaiyama aldol products with outstanding enantioselectivities. In this paper, we describe an optimized ligand synthesis, trends in stereoselectivity that result from changing lanthanide ions, and an exploration of substrate scope that includes aromatic and aliphatic aldehydes and silyl enol ethers derived from aromatic and aliphatic ketones.

A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions

The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral β-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded β-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.

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.

Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates

Enolates of (S)-N,N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee.

Design and synthesis of aromatic inhibitors of anthranilate synthase

Anthranilate synthase catalyses the conversion of chorismate to anthranilate, a key step in tryptophan biosynthesis. A series of 3-(1-carboxy-ethoxy) benzoic acids were synthesised as chorismate analogues, with varying functionality at C-4, the position of the departing hydroxyl group in chorismate. Most of the compounds were moderate inhibitors of anthranilate synthase, with inhibition constants between 20-30 μM. The exception was 3-(1-carboxy-ethoxy) benzoic acid, (C-4 = H), for which K1 = 2.4 μM. These results suggest that a hydrogen bonding interaction with the active site general acid (Glu309) is less important than previously assumed for inhibition of the enzyme by these aromatic chorismate analogues. The Royal Society of Chemistry 2005.

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.

Difference in the behavior of methyl (S)-α-bromopropionate in its addition to trimethylvinylsilane depending on the method of initiation

The addition of methyl (S)-2-bromopropionate to trimethylvinylsilane initiated by systems based on iron pentacarbonyl affords a racemic adduct and is accompanied by racemization of the unreacted chiral ester. In the presence of benzoyl peroxide, the reaction proceeds similarly, but no racemization of the starting chiral ester occurs.

Process for the preparation of brominated compounds, especially from alcohols

A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.