29624-04-2

Basic information

• Product Name: Benzenesulfinic acid, phenylmethyl ester
• CAS NO: 29624-04-2
• Molecular Formula: C13H12O2S
• Molecular Weight: 232.303
• Mol File: 29624-04-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Benzenesulfinic acid, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfinic acid, phenylmethyl ester(29624-04-2)
• EPA Substance Registry System: Benzenesulfinic acid, phenylmethyl ester(29624-04-2)

Safety Data

• Hazardous Substances Data: 29624-04-2(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 100-39-0 benzyl bromide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-09-9 benzenesulfonyl chloride 
• 873-55-2 sodium benzenesulfonate 
• 100-51-6 benzyl alcohol 
• 1666-16-6 N-benzylidene-N'-benzenesulfonylhydrazone 
• 80-17-1 benzenesufonyl hydrazide 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 618-41-7 Benzenesulfinic acid 
• 6738-17-6 (Z)-benzyl N,N'-dicyclohexylcarbamimidate 

Downstream Products

• 1193-82-4 racemic methyl phenyl sulfoxide 
• 100-51-6 benzyl alcohol 

Relevant articles and documents

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.).

Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism

Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.

Wittig Ylide Mediated Decomposition of N -Sulfonylhydrazones to Sulfinates

N-Sulfonylhydrazones generate sulfinates selectively when treated with a stabilized Wittig ylide in a polar aprotic solvent at elevated temperature. The transition metal and base free decomposition method is applicable to N-sulfonylhydrazones generated from a number of aromatic and heteroaromatic aldehydes and ketones. In the case of N-tosylhydrazones derived from O-allyl and O-propargyl salicylaldehydes, selective formation of sulfinate occurs over intramolecular [3 + 2]-cycloaddition reaction.