51594-57-1

Basic information

• Product Name: (R)-Epibromohydrine
• Synonyms: (2R)-2-(Bromomethyl)oxirane;(R)-2-(Bromomethyl)oxirane;(R)-Epibromohydrine;[R,(-)]-2-Bromomethyloxirane;(R)-(-)-Epibromohydrin
• CAS NO: 51594-57-1
• Molecular Formula: C₃H₅BrO
• Molecular Weight: 136.98
• Mol File: 51594-57-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 138 °C
• Appearance: /
• Density: 1.744±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-Epibromohydrine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Epibromohydrine(51594-57-1)
• EPA Substance Registry System: (R)-Epibromohydrine(51594-57-1)

Safety Data

• Hazardous Substances Data: 51594-57-1(Hazardous Substances Data)

Usage

Description

(R)-Epibromohydrine, also known as (R)-1,2-Epoxy-3-bromopropane, is a chemical compound that serves as a crucial intermediate in the synthesis of pharmaceuticals and fine chemicals. As a chiral compound, it exists in two enantiomeric forms, (R)and (S)-, with the (R)-enantiomer being predominantly utilized in industrial applications. Characterized by its high reactivity due to the epoxide and bromine functional groups, (R)-Epibromohydrine readily participates in nucleophilic substitution reactions with various nucleophiles, such as amines and thiolates. However, it is also recognized as a hazardous substance that can cause skin and respiratory irritation, necessitating careful handling in controlled environments.

Uses

Used in Pharmaceutical Synthesis:
(R)-Epibromohydrine is used as a key intermediate for the production of various pharmaceuticals and fine chemicals. Its unique reactivity allows for the creation of a wide range of compounds with different therapeutic applications.
Used in Chemical Synthesis:
(R)-Epibromohydrine is utilized as a building block in the synthesis of complex organic molecules, taking advantage of its propensity to undergo nucleophilic substitution reactions with a variety of nucleophiles.
Used in Research and Development:
In the field of research and development, (R)-Epibromohydrine is employed as a versatile compound for exploring new chemical reactions and developing innovative synthetic pathways.
Used in Industrial Processes:
(R)-Epibromohydrine is used as a critical component in various industrial processes, particularly in the manufacturing of specialty chemicals and pharmaceutical products.

Upstream product

• 83398-54-3 Toluene-4-sulfonic acid (R)-3-bromo-2-hydroxy-propyl ester 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 83165-36-0 (2S)-2,3-dibromopropan-1-ol 
• 96-21-9 1,3-dibromo-2-hydroxypropane 

Relevant articles and documents

Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium

A gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20?mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99% ee and 34.5% yield. Moreover, AbHHDH catalyzed the azidolysis of epoxides with low to moderate (S)-enantioselectivity. The highest enantioselectivity (E = 18.6) was observed when (R,S)-benzyl glycidyl ether was used as the substrate. A sequential kinetic resolution catalyzed by HHDH was employed for the synthesis of chiral 1-chloro-3-phenoxy-2-propanol. We prepared enantiopure (S)-isomer with a high enantiopurity of ee > 99% and a yield of 30.7% (E-value: 21.3) by kinetic resolution of 20?mM substrate. The (S)-isomer with 99% ee readily obtained from 40 to 150?mM (R,S)-1-chloro-3-phenoxy-2-propanol. Taken together, the results of this study demonstrate the applicability of this HHDH for the production of optically active compounds. [Figure not available: see fulltext.].

Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography

Molecular organic cage compounds have attracted considerable attention due to their potential applications in gas storage, catalysis, chemical sensing, molecular separations, etc. In this study, a homochiral pentyl cage compound was synthesized from a condensation reaction of (S,S)-1,2-pentyl-1,2-diaminoethane and 1,3,5-triformylbenzene. The imine-linked pentyl cage diluted with a polysiloxane (OV-1701) was explored as a novel stationary phase for high-resolution gas chromatographic separation of organic compounds. Some positional isomers were baseline separated on the pentyl cage-coated capillary column. In particular, various types of enantiomers including chiral alcohols, esters, ethers and epoxides can be resolved without derivatization on the pentyl cage-coated capillary column. The reproducibility of the pentyl cage-coated capillary column for separation was investigated using nitrochlorobenzene and styrene oxide as analytes. The results indicate that the column has good stability and separation reproducibility after being repeatedly used. This work demonstrates that molecular organic cage compounds could become a novel class of chiral separation media in the near future.

Enzymatic dynamic kinetic resolution of epihalohydrins

The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N 3- are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N3-, combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N3- was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N 3- and Br-, the product (S)-1-azido-3-bromo-2- propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks.