54697-52-8

Basic information

• Product Name: 2,3-dimethylthiirane 1,1-dioxide
• CAS NO: 54697-52-8
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.1701
• Mol File: 54697-52-8.mol

Chemical Properties

• Boiling Point: 639.7°C at 760 mmHg
• Flash Point: 511.8°C
• Density: 1.204g/cm³
• Vapor Pressure: 1.46E-15mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: 2,3-dimethylthiirane 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethylthiirane 1,1-dioxide(54697-52-8)
• EPA Substance Registry System: 2,3-dimethylthiirane 1,1-dioxide(54697-52-8)

Safety Data

• Hazardous Substances Data: 54697-52-8(Hazardous Substances Data)

Upstream product

• 594-44-5 Ethanesulfonyl chloride 

Relevant articles and documents

Episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates

Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and Bu′-P4 phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2. The structure of a trisilylated episulfone product, 2a, was determined by X-ray crystallography. In the absence of Me3SiCl, reaction of episulfones with lithium diisopropylamide results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.

Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines. 2. Formation of Episulfones, Sulfonylsulfene - Amine S,N-Adducts and Chlorsulfines from Primary Sulfonyl Chlorides and Tertiary Amines

The reaction of primary sulfonyl chlorides 1b-m with the tertiary amine bases quinuclidine, DABCO, Me3N, Et3N, Bu3N, EtiPr2N, and 1,2,2,6,6-pentamethylpiperidine is studied in acetonitrile solution between -40 and 80 deg C.The 2,3-dialkylthiirane 1,1-dioxides 4 (trans/cis > 1) and the alkenes 5 1> are obtained in high yields with Et3N at -40 deg C.The stereochemistry is influenced by the amine base B in the ring-closure reaction and partially by epimerization of the episulfones 4.Hindered bases favor the cis, β-branched sulfonyl chlorides the trans isomer.Competing formation of the sulfonylsulfene - amine S,N-adducts 7 is only observed with quinuclidine, DABCO, and Me3N, which are also the most active amines in the epimerization of the cis-2,3-diarylthiirane 1,1-dioxides 4.Methanesulfonyl chloride (1a) yields the mesylsulfene - amine S,N-adducts 7a with Me3N and Et3N in MeCN, but thiirane 1,1-dioxide (4a) with EtiPr2N in MeCN or with Et3N in Et2O.Formation of chlorosulfines 10 is favored by higher temperature (T > 20 deg C), hindered amine bases and β-branched sulfonyl chlorides.Isolation of 10g and 10h in high yields shows that tert-alkylchlorosulfines are rather stable sulfines.