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alpha-Toluenesulfonyl chloride

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alpha-Toluenesulfonyl chloride Basic information
Synthesis
Product Name:alpha-Toluenesulfonyl chloride
Synonyms:α-Toluenesulfonyl chloride ,98%;Benzylsulfonyl chlorideDISC 06/12/2000;Phenylmethanesulphonyl chloride;alpha-Toluenesulfonyl chloride, 98% 5GR;NSC 41894;Toluen-alphaSulfonyl chloride;ALPHA TOLUENE SULHONYL CHLORIDE;Benzenemethanesulfonylchloride
CAS:1939-99-7
MF:C7H7ClO2S
MW:190.65
EINECS:217-717-1
Product Categories:Building Blocks;Chemical Synthesis;Pharmaceutical Intermediates;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Benzene derivatives;Benzenesulfonyl chloride
Mol File:1939-99-7.mol
alpha-Toluenesulfonyl chloride Structure
alpha-Toluenesulfonyl chloride Chemical Properties
Melting point 92-94 °C(lit.)
Boiling point 120 °C / 10mmHg
density 1.3264 (estimate)
refractive index 1.624-1.626
storage temp. Inert atmosphere,2-8°C
solubility soluble in Toluene
form Crystalline Powder
color Almost white
Water Solubility decomposes
Sensitive Moisture Sensitive
BRN 972806
InChI1S/C7H7ClO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
InChIKeyOAHKWDDSKCRNFE-UHFFFAOYSA-N
SMILESClS(=O)(=O)Cc1ccccc1
CAS DataBase Reference1939-99-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenemethanesulfonyl chloride(1939-99-7)
EPA Substance Registry SystemBenzenemethanesulfonyl chloride (1939-99-7)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45
RIDADR UN 3261 8/PG 2
WGK Germany 3
F 10-21
Hazard Note Corrosive
TSCA TSCA listed
HazardClass 8
PackingGroup II
HS Code 29049020
Storage Class8A - Combustible corrosive hazardous materials
Hazard ClassificationsSkin Corr. 1B
MSDS Information
ProviderLanguage
Benzylsulfonyl chloride English
SigmaAldrich English
ACROS English
ALFA English
alpha-Toluenesulfonyl chloride Usage And Synthesis
Synthesis

Starting with benzaldehyde, a benzothiourea structure is generated through reduction, chlorination, and substitution reactions. Finally, alpha-Toluenesulfonyl chloride is obtained via sulfonyl chloride reaction.

Sulfoyl chloride reaction yields alpha-Toluenesulfonyl chloride

Chemical Propertiesalmost white crystalline powder
Usesa-Toluenesulfonyl Chloride inhibits intracellular protein breakdown in the L1210 ascites leukemia in mouse. It also functions as a reagent for the protection of amino groups as benzylsulfonamides which can be cleaved off through reduction.
Synthesis Reference(s)The Journal of Organic Chemistry, 16, p. 621, 1951 DOI: 10.1021/jo01144a013
Synthesis, p. 1203, 1992 DOI: 10.1055/s-1992-26333
General DescriptionPhenylmethanesulfonyl chloride is an aliphatic sulfonyl chloride. It reacts with triethylamine in methylene chloride or ether to yield trans-stilbene and cis diphenylethylene sulfone. Its reaction with 1,1-bis(diethylamino)ethane has been studied. Addition of phenylmethanesulfonyl chloride to 1,3-diphenyl-2-pyrrolidinopropene in the presence of water was studied.
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