5787-32-6

Basic information

• Product Name: [S,(+)]-2-Bromobutane
• Synonyms: [S,(+)]-2-Bromobutane
• CAS NO: 5787-32-6
• Molecular Formula: C₄H₉Br
• Molecular Weight: 137.02
• Mol File: 5787-32-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [S,(+)]-2-Bromobutane(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(+)]-2-Bromobutane(5787-32-6)
• EPA Substance Registry System: [S,(+)]-2-Bromobutane(5787-32-6)

Safety Data

• Hazardous Substances Data: 5787-32-6(Hazardous Substances Data)

Usage

Description

[S,(+)]-2-Bromobutane, also known as (S)-2-Bromobutane, is a colorless liquid chemical compound with the molecular formula C4H9Br. It is a halogenated hydrocarbon, specifically a bromoalkane, and is recognized for its role in organic synthesis reactions. As a chiral compound, it possesses two enantiomers, with the S-(+)-enantiomer being the biologically active form. While it is utilized in various industrial applications, it is also considered moderately toxic and requires careful handling to prevent environmental hazards.

Uses

Used in Pharmaceutical Industry:
[S,(+)]-2-Bromobutane is used as a synthetic building block for the production of various pharmaceuticals. Its unique chemical properties allow it to be a valuable component in the creation of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, [S,(+)]-2-Bromobutane is used as an intermediate in the synthesis of different agrochemicals, contributing to the development of products that enhance crop protection and management.
Used as a Solvent:
Due to its properties as a halogenated hydrocarbon, [S,(+)]-2-Bromobutane is also utilized as a solvent in various chemical processes, facilitating reactions and improving the efficiency of certain industrial procedures.

Upstream product

• 78-76-2 s-butyl bromide 
• 106251-39-2 (R)-(-)-diisopropylneopentyl-sec-butyltin 
• 62736-86-1 (R)-(-)-triisopropyl-sec-butyltin 
• 14898-79-4 (2R)-butan-2-ol 
• 4221-99-2 (S)-2-butanol 

Downstream Products

• 35778-39-3 3-methyl-4-nonanone 
• 53716-55-5 L-2-deuterio-butane 
• 66292-26-0 (+)-4-methyl-1,1-diphenylhex-1-ene 
• 124292-35-9 (+)-4-methyl-3,3-diphenylhex-1-ene 
• 124292-34-8 (+)-4-methyl-3-phenylhex-1-ene 
• 81928-51-0 (C₆H₅)3SnCH(CH₃)C₂H₅ 
• 122876-32-8 trans-15,16-di-sec-butyl-1,4,8,11-ethanediylidene<14>annulene 
• 139914-65-1 C₂₄H₂₈ 
• 77080-43-4 trans-15,16-dimethyl-1,4,8,11-ethanediylidene<14>annulene 
• 139942-99-7 trans-15-sec-butyl-16-methyl-1,4,8,11-ethanediylidene<14>annulene 
• 119785-70-5 (S)-(+)-s-butyl phenyl sulfide 
• 49623-67-8 (S)-3-bromo-1-chloro-butane 
• 49623-65-6 (2S)-erythro-2-bromo-3-chloro-butane 
• 49623-68-9 (R)-1-bromo-2-chloro-butane 

Relevant articles and documents

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.

Stereochemistries and mechanisms of reactions of electrophiles with organotin compounds

The effect of solvent and electrophile on halodemetalation reactions of carbon-tin bonds has been investigated. Both stereochemical results and 119Sn NMR have been used as mechanistic probes. The effect of solvent is extreme; reactions performed in polar solvents such as acetonitrile and dimethylformamide yield cleavage products with predominantly inversion of configuration, whereas nonpolar solvents yield products with predominantly retention. Polar-aprotic solvents appear to be highly efficient in promoting inversion stereochemistry. Polar-protic solvents are not as efficient. This is explained in terms of some very specific solvation phenomena. Also, 119Sn NMR studies of several trialkyltin halides in various solvents show that these specific solvation phenomena can be qualitatively assessed. The nature of the electrophile also plays an important role in eventual stereochemistry; Br2, I2, ICl, and IBr are compared and discussed.