5787-33-7

Basic information

• Product Name: [R,(-)]-2-Bromobutane
• Synonyms: [R,(-)]-2-Bromobutane
• CAS NO: 5787-33-7
• Molecular Formula: C₄H₉Br
• Molecular Weight: 137.02
• Mol File: 5787-33-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 90.7±8.0 °C(Predicted)
• Appearance: /
• Density: 1.267±0.06 g/cm3(Predicted)
• CAS DataBase Reference: [R,(-)]-2-Bromobutane(CAS DataBase Reference)
• NIST Chemistry Reference: [R,(-)]-2-Bromobutane(5787-33-7)
• EPA Substance Registry System: [R,(-)]-2-Bromobutane(5787-33-7)

Safety Data

• Hazardous Substances Data: 5787-33-7(Hazardous Substances Data)

Usage

General Description

[R,(-)]-2-Bromobutane, also known as (R)-2-Bromobutane, is an organic compound with the chemical formula C4H9Br. It is a colorless liquid that is commonly used as a solvent and as an intermediate in organic synthesis. The compound is chiral, with the R-enantiomer being the naturally occurring form. It is commonly used in the production of pharmaceuticals, agrochemicals, and flavors, as well as in the synthesis of other organic compounds. [R,(-)]-2-Bromobutane is also known for its use as a reagent in organic chemistry reactions, particularly in nucleophilic substitution reactions. Due to its reactivity and potential health hazards, proper safety precautions should be followed when handling this compound.

Upstream product

• 14898-79-4 (2R)-butan-2-ol 
• 4221-99-2 (S)-2-butanol 
• 62736-86-1 (R)-(-)-triisopropyl-sec-butyltin 
• 106251-39-2 (R)-(-)-diisopropylneopentyl-sec-butyltin 
• 78-76-2 s-butyl bromide 
• 357-57-3 brucine 

Downstream Products

• 31688-64-9 2-(2-butyl)quinoxaline 
• 66292-26-0 (+)-4-methyl-1,1-diphenylhex-1-ene 
• 124292-35-9 (+)-4-methyl-3,3-diphenylhex-1-ene 
• 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 
• 122876-32-8 trans-15,16-di-sec-butyl-1,4,8,11-ethanediylidene<14>annulene 
• 139914-65-1 C₂₄H₂₈ 
• 53716-55-5 L-2-deuterio-butane 
• 81928-51-0 (C₆H₅)3SnCH(CH₃)C₂H₅ 
• 85181-64-2 (+)-(S)-3-(2-methylbutyl)pyridine 
• 119785-70-5 (S)-(+)-s-butyl phenyl sulfide 
• 111170-67-3 2-sec-butyl-2-(methoxycarbonyl)-1-indanone 
• 111170-67-3 2-((R)-sec-Butyl)-1-oxo-indan-2-carboxylic acid methyl ester 
• 111170-67-3 2-sec-butyl-2-(methoxycarbonyl)-1-indanone 

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.

Asymmetric Alkylation of β-Keto Esters with Optically Active Sulfonium Salts

Alkylation of the cyclic β-keto ester2-(methoxycarbonyl)-1-indanone (2) with racemic alkylsulfonium salts 1a-h gave 2-alkylindanones 3 and 4 in 60-96percent yields.The relative reactivities of the alkyl substituents of aryldialkylsulfonium salts 1e and 1f were quite different from those in SN2 alkylations.Asymmetric induction occured upon alkylation of 2 with optically active sulfonium salts. (R)-2-Ethyl-2-(methoxycarbonyl)cyclohexanone (11) was obtained in up to 16percent ee by alkylation of the enolate ion of 2-(methoxycarbonyl)cyclohexanone (9) with optically active (R)-(+)-(p-chlorophenyl)ethylmethylsulfonium d-10-camphorsulfonate (1k).Alkylation of the enolate ion of 2 with sulfonium salts containing optically active alkyl groups afforded C-alkylated products with inversion of configuration at the asymmetric alkyl carbon atom.These alkylations appear to proceed via an S-O sulfurane intermediate or a tight ion pair with subsequent stereoselective alkyl migration to the enolate.