31562-43-3

Basic information

• Product Name: tert-Butylsulfinyl chloride
• Synonyms: TERT-BUTYLSULFINYL CHLORIDE 97;T-BUTYLSULFINYL CHLORIDE, 97%;tert-Butylsulfinyl chloride;2-Methyl-2-propanesulfinyl chloride;2-METHYLPROPANE-2-SULFINIC CHLORIDE;tert-Butylsulfinyl chloride 97%
• CAS NO: 31562-43-3
• Molecular Formula: C₄H₉ClOS
• Molecular Weight: 140.63
• Product Categories: Sulfinyl Halides;Organic Building Blocks;Sulfur Compounds;Sulfinyl Halides;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 31562-43-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 53-54 °C19 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 1.135 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.65mmHg at 25°C
• Refractive Index: n20/D 1.4830(lit.)
• CAS DataBase Reference: tert-Butylsulfinyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butylsulfinyl chloride(31562-43-3)
• EPA Substance Registry System: tert-Butylsulfinyl chloride(31562-43-3)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 31562-43-3(Hazardous Substances Data)

Usage

Uses

tert-butylsulfinyl chloride can react with primary and secondary amines to form tert-butylsulfinamides, which on oxidation forms base stable tert-butylsulfonamide. It can also react with 1-thiosugars to form the corresponding carbohydrate thionolactones.

General Description

tert-Butylsulfinyl chloride can be synthesized by using tert-butylmagnesium chloride as the starting material via a multi-step synthesis process.

InChI:InChI=1/C4H9ClOS/c1-4(2,3)7(5)6/h1-3H3

Upstream product

• 1133989-31-7 N-(1-methylcyclohexyl)-tert-butanesulfinamide 
• 247236-71-1 (R_S)-2-methyl-N-((R)-1-phenylethyl)propane-2-sulfinamide 
• 10490-22-9 tert-butylsulfonyl chloride 

Downstream Products

• 628-13-7 pyridine hydrochloride 
• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 
• 507-20-0 tertiary butyl chloride 
• 10490-22-9 tert-butylsulfonyl chloride 
• 31562-41-1 di-tert-butyl thiosulfonate 
• 62383-66-8 tert-butylsulfenic tert-butylsulfinic dithioanhydride 
• 112882-05-0 2-Methyl-propane-2-sulfonic acid 2-benzyloxy-ethyl ester 
• 3144-09-0 methanesulfonamide 
• 75975-45-0 trifluoromethane sulfonic anhydride 
• 75975-41-6 C₅H₁₃NO₄S₂ 
• 89523-58-0 C₁₁H₁₆OS₂ 
• 89523-59-1 S-phenyl 2-methylpropane-2-sulfinothioate 
• 76699-24-6 N,2-dimethylpropane-2-sulfinamide 

Relevant articles and documents

The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2.

Aminohydroxylation of olefins with tert-alkyl sulfonamides

Tert-alkyl sulfonamides chloramine salts are used as nitrogen sources in the catalytic aminohydroxylation and/or aziridination of olefins. The tert-alkyl sulfonamides chloramine salts are close to Chloramine T with respect to their reactivity as nitrogen sources with olefins. However, unlike the tosyl sulfonyl amine group of Chloramine T, the resulting t-alkyl sulfonylamino functionalities can be easily converted to an unprotected amine under mild acidic conditions making the method a simple and cost efficient approach for producing unsubstituted hydroxy amine and/or aziridine products.