670-98-4

Basic information

• Product Name: METHYL BENZENESULFINATE
• Synonyms: MeOS(O)Ph;Methylebenzenesulfinate;METHYL BENZENESULFINATE;Benzenesulfinicacidmethylester;Methyl benzenesulphinate;Methyl phenylsulfinate;Methyl benzenesulfinate 98%
• CAS NO: 670-98-4
• Molecular Formula: C₇H₈O₂S
• Molecular Weight: 156.2
• Product Categories: Organic Building Blocks;Sulfonates/Sulfinates;Sulfur Compounds
• Mol File: 670-98-4.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 79-83°C 0,3mm
• Flash Point: 91°C
• Appearance: Colorless to pale yellow/Liquid
• Density: 1,194 g/cm3
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: METHYL BENZENESULFINATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL BENZENESULFINATE(670-98-4)
• EPA Substance Registry System: METHYL BENZENESULFINATE(670-98-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 670-98-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 670-98-4 differently. You can refer to the following data:
1. Methyl Benzenesulfinate is a reagent used in the synthesis of sulfinyl compounds.
2. Methyl benzenesulfinate may be employed for the synthesis of symmetrical disulfides.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 723, 1973Tetrahedron Letters, 13, p. 5313, 1972 DOI: 10.1016/S0040-4039(01)85238-2

General Description

Methyl benzenesulfinate is an ester of aromatic sulfinic acid. It reacts smoothly with thionyl chloride at room temperature to afford sulfinyl chloride and methyl chlorosulfonate.

InChI:InChI=1/C7H8O2S/c1-9-10(8)7-5-3-2-4-6-7/h2-6H,1H3

Upstream product

• 67-56-1 methanol 
• 618-41-7 Benzenesulfinic acid 
• 39574-20-4 2-benzenesulfonyl-pyridine N-oxide 
• 24244-60-8 2-(phenylsulfonyl)pyridine 
• 75-05-8 acetonitrile 
• 672-36-6 phenylsulphur trifluoride 
• 100-51-6 benzyl alcohol 
• 108-98-5 thiophenol 
• 80-17-1 benzenesufonyl hydrazide 
• 4972-29-6 benzenesulphinyl chloride 
• 882-33-7 diphenyldisulfane 
• 931-59-9 benzenesulfenyl chloride 
• 98-09-9 benzenesulfonyl chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 67-56-1 methanol 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 108-98-5 thiophenol 
• 98877-49-7 3-(phenylsulfinyl)bicyclo<3.2.0>hept-en-2-one 
• 111119-47-2 3β-methoxy-16ξ-phenylsulfinyl-5α-androstan-17-one 
• 111119-49-4 16ξ-phenylsulfinyl-3β-phenylsylfinyloxy-5β-androstan-17-one 
• 49833-32-1 1-phenyl-1-(phenylsulfinyl)-ethene 
• 87295-68-9 Z-3-(benzenesulfinyl)-2-ethylprop-2-en-1-ol 
• 87309-96-4 Z-3-benzenesulfinyl-2-phenylprop-2-en-1-ol 
• 73509-29-2 t-2,t-7-dimethyl-4-(phenylsulfinyl)-t-8-(t-butyloxy)-r-1H-bicyclo<5.3.0>decan-5-one 
• 111263-94-6 (3S,5R,8R,9S,10S,13S,14S)-16-Benzenesulfinyl-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-one 
• 149705-58-8 5-Benzenesulfinyl-3-methoxymethoxymethyl-6,7-dihydro-5H-benzofuran-4-one 
• 55980-76-2 2-(phenylsullfinyl)cyclopentanone 
• 111119-48-3 3β-hydroxy-16ξ-phenylsulfinyl-5-androsten-17-one 3-tetrahydropyranyl ether 

Relevant articles and documents

Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides

In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.

Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates

The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).

Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides

It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry.