22156-91-8

Basic information

• Product Name: [S,(+)]-2-Chlorobutane
• Synonyms: [S,(+)]-2-Chlorobutane
• CAS NO: 22156-91-8
• Molecular Formula: C₄H₉Cl
• Molecular Weight: 0
• Mol File: 22156-91-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [S,(+)]-2-Chlorobutane(CAS DataBase Reference)
• NIST Chemistry Reference: [S,(+)]-2-Chlorobutane(22156-91-8)
• EPA Substance Registry System: [S,(+)]-2-Chlorobutane(22156-91-8)

Safety Data

• Hazardous Substances Data: 22156-91-8(Hazardous Substances Data)

Upstream product

• 78-86-4 s-butyl chloride 
• 4221-99-2 (S)-2-butanol 
• 78-92-2 (S)-(-)-sec-butyl alcohol 
• 22598-58-9 chlorosulfurous acid (R)-sec-butyl ester 
• 108-88-3 toluene 
• 14898-79-4 (2R)-butan-2-ol 

Downstream Products

• 583-48-2 3,4-dimethylhexane 
• 81928-51-0 (C₆H₅)3SnCH(CH₃)C₂H₅ 
• 2432-39-5 (R)-S-sec-butyl ethanethioate 
• 1595-16-0 1-sec-butyl-4-methylbenzene 
• 1595-06-8 2-sec-butyltoluene 
• 1772-10-7 2-(m-tolyl)butane 
• 135-98-8 (2R)-sec-butylbenzene 

Relevant articles and documents

Stereochemical dissection of a carbene fragmentation reaction

The fragmentation of (S)-3-(2-butoxy)-3-chlorodiazirine (9) in acetonitrile proceeds via N2 loss to (5)-2-butoxy-chlorocarbene (10) and thence via CO scission to a 2-butyl cation/chloride anion pair (11) that collapses to (5)-2-chlorobutane (12) with ～56% net retention. In 1-butanol, ion pair 11 affords 55% chloride 12 by ion pair return with 82% net retention and 45% of (R)-2-butyl 1-butyl ether (13) by ion pair solvolysis with ～71% net inversion.

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.

Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation

The reactivity of bismuth(III) halides (BiX3; X=Cl, Br and I) towards a series of alcohols has been investigated. Three different reactions have been studied, namely: halogenation, dehydration and etherification. The behaviour of these bismuth derivatives was found to depend on the nature of the halide bonded to the bismuth atom. Their reactivities can be interpreted on the basis of the Hard and Soft Acids and Bases (HSAB) principle. A mechanism is proposed which involves the formation of a complex of the alcohol with Bi(III).