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

Description

METHYL BENZENESULFINATE is an organic compound that serves as a reagent in the synthesis of various chemical compounds, particularly sulfinyl compounds and symmetrical disulfides. It is known for its ability to facilitate the formation of these compounds, making it a valuable component in chemical reactions.

Uses

Used in Chemical Synthesis:
METHYL BENZENESULFINATE is used as a reagent for the synthesis of sulfinyl compounds, which are important intermediates in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its presence in the reaction helps to form the desired sulfinyl compounds efficiently.
Used in Symmetric Disulfide Synthesis:
METHYL BENZENESULFINATE is also used in the synthesis of symmetrical disulfides, which are compounds containing two identical thiol groups connected by a disulfide bond. These symmetrical disulfides have applications in various industries, including the production of rubber, dyes, and pharmaceuticals.

Synthesis Reference(s)

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

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

Upstream product

• 67-56-1 methanol 
• 4972-29-6 benzenesulphinyl chloride 
• 40167-15-5 N-(phenylsulphinyl)phthalimide 
• 108-98-5 thiophenol 
• 126114-20-3 O-methyl-N-(1S,2S,5S)-myrtanyl-N'-phenylisourea 
• 618-41-7 Benzenesulfinic acid 
• 126114-21-4 O-methyl-N,N'-di-(R)-α-phenylethylisourea 
• 6257-10-9 N,N'-dicyclohexyl-O-methyl isourea 
• 873-55-2 sodium benzenesulfonate 
• 74-88-4 methyl iodide 
• 100-68-5 methyl-phenyl-thioether 
• 75-05-8 acetonitrile 
• 863211-81-8 1-((S)-Benzenesulfinyl)-piperidine 
• 672-36-6 phenylsulphur trifluoride 

Downstream Products

• 67-56-1 methanol 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 108-98-5 thiophenol 
• 1859-03-6 ethyl benzenesulfinate 
• 146916-38-3 <(Oct-1-ynyl)sulfinyl>benzene 
• 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 

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.

NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (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.