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

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

• 4972-29-6 benzenesulphinyl chloride 
• 14642-79-6 benzyloxy-trimethylsilane 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 126114-22-5 O-benzyl-N,N'-di-(R)-α-phenylethylisourea 
• 6738-17-6 (Z)-benzyl N,N'-dicyclohexylcarbamimidate 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 80-17-1 benzenesufonyl hydrazide 
• 873-55-2 sodium benzenesulfonate 
• 98-09-9 benzenesulfonyl chloride 
• 100-39-0 benzyl bromide 

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.).

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

Metal- And oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols

An efficient and eco-friendly electrochemical synthesis of various sulfinic esters from thiols and alcohols via sequential S-H/S bond cleavage and double S-O bond formation under mild reaction conditions has been developed. Stoichiometric oxidants, metal catalysts, activating agents and even added bases were avoided in this method, and the only by-product generated from this reaction was dihydrogen gas which could serve as a green source of energy. Various functional groups are compatible with this green protocol which can be easily conducted on a gram-scale.

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.

Facile aerobic photo-oxidative synthesis of sulfinic esters

A mild and efficient one-pot visible light-induced method has been developed for the synthesis of sulfinic esters. Sulfinic esters are important structural elements that are frequently found in pharmaceutical agents and biologically active natural products. The routine procedure in the drug discovery and development process to prepare and fully characterize sulfinic esters make them a drug candidate for biological evaluation.

A sustainable oxidative esterification of thiols with alcohols by a cobalt nanocatalyst supported on doped carbon

Here, we developed a new cobalt nanocatalyst supported on N-SiO2-doped activated carbon (Co/N-SiO2-AC), which exhibits excellent catalytic performance towards the oxidative esterification of (hetero)aryl and alkyl thiols with alcohols. A wide array of sulfinic esters were efficiently afforded in an exclusive chemoselective manner. The developed synthetic method proceeds with the merits of mild reaction conditions, broad substrate scope, operational simplicity, good functional group tolerance, earth-abundant and reusable cobalt catalysts, the utilization of renewable alcohols as the coupling partners and molecular O2 as the sole oxidant, which offers a practical method for sustainable synthesis of sulfinic esters.

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.

Copper-Catalyzed Aerobic Formation of Unstable Sulfinyl Radicals for the Synthesis of Sulfinates and Thiosulfonates

Copper-catalyzed aerobic coupling of thiols and alcohols affords sulfinates and thiosulfonates. These products are assumed to form via sulfinyl radicals which are not commonly found in oxidative coupling reactions of thiols. A reaction mechanism involving sulfinyl radicals is proposed, and mass and electron paramagnetic resonance (EPR) experimental results are provided.

Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates

A Cu-catalyzed aerobic oxidative reaction between sulfonyl hydrazides and alcohols has been developed. In this reaction, sulfonyl hydrazides act as the sulfinic acid precursors to react with alcohols, resulting in sulfinic esters with up to 72 % yield. This catalytic system tolerates a wide range of sulfonyl hydrazide substrates, and represents a new strategy for the transformation of readily available sulfonyl hydrazides.

An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides

(Chemical Equation Presented) In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellen