22157-31-9

Basic information

• Product Name: (R)-sec-Butyl chloride
• Synonyms: (R)-sec-Butyl chloride;[R,(-)]-2-Chlorobutane
• CAS NO: 22157-31-9
• Molecular Formula: C₄H₉Cl
• Molecular Weight: 0
• Mol File: 22157-31-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 69.2°C at 760 mmHg
• Appearance: /
• Density: 0.87g/cm³
• Vapor Pressure: 147mmHg at 25°C
• Refractive Index: 1.393
• CAS DataBase Reference: (R)-sec-Butyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-sec-Butyl chloride(22157-31-9)
• EPA Substance Registry System: (R)-sec-Butyl chloride(22157-31-9)

Safety Data

• Hazardous Substances Data: 22157-31-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H9Cl/c1-3-4(2)5/h4H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 4221-99-2 (S)-2-butanol 
• 78-86-4 s-butyl chloride 
• 66610-39-7 (S)-2-methoxy-butane 
• 7646-78-8 tin(IV) chloride 
• 75-36-5 acetyl chloride 
• 123-91-1 1,4-dioxane 
• 22598-58-9 chlorosulfurous acid (R)-sec-butyl ester 
• 109-99-9 tetrahydrofuran 

Relevant articles and documents

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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.

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.