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

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 
• 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 
• 4221-99-2 (S)-2-butanol 

Downstream Products

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

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.

N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity

A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives we examined, the N-sec-butylthio β-lactam derivative 5g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochemistry within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams 15a-d, the 3R,4S-lactams 15c, d are more active than the 3S,4R-stereoisomers 15a, b in agar diffusion experiments. The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target.

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).

Stereochemistry of Friedel-Crafts Alkylation of Benzene with Optically Active 2-Chlorobutane

The alkylation of benzene with (+)-2-chlorobutane (1) by Lewis acid catalyst gave stereospecifically (-)-2-phenylbutane (2) with inversion of configuration at low temperature for short reaction time.A lowering of the stereospecificity of the reaction was found to be partly due to the racemization of (+)-1- and (-)-2.