19552-10-4

Usage

Uses

Used in Chemical Synthesis:
4-BROMOBENZYL MERCAPTAN is used as a synthetic intermediate for the production of various organic compounds. Its ability to undergo desulfurization reactions makes it a valuable precursor in the synthesis of other molecules.
Used in Pharmaceutical Industry:
4-BROMOBENZYL MERCAPTAN is used as a building block for the development of pharmaceutical compounds. Its unique structure can be exploited to create new drugs with potential therapeutic applications.
Used in Chemical Research:
4-BROMOBENZYL MERCAPTAN serves as a research tool in the field of organic chemistry. It can be used to study the reactivity of different functional groups and to develop new synthetic methodologies.
Used in the Synthesis of 4-Bromotoluene:
4-BROMOBENZYL MERCAPTAN is used as a starting material for the synthesis of 4-bromotoluene via desulfurization with molybdenum hexacarbonyl [Mo(CO)6] in tetrahydrofuran. This reaction is an example of its utility in chemical synthesis, particularly in the production of substituted aromatic compounds.

InChI:InChI=1/C7H7BrS/c8-7-3-1-6(5-9)2-4-7/h1-4,9H,5H2

Upstream product

• 17356-08-0 thiourea 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 46123-94-8 S-(4-bromo-benzyl)-isothiourea 
• 111039-41-9 4-bromobenzyl carbamimidothioate monohydrobromide 
• 108-24-7 acetic anhydride 
• 873-75-6 4-bromobenzenemethanol 
• 351003-15-1 thioacetic acid S-(4-bromo-benzyl)ester 
• 237763-11-0 methanesulfonic acid 4-bromo-benzyl ester 
• 589-17-3 p-bromobenzyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 1892-20-2 4-bromobenzyl carbamate 
• 131887-59-7 [(4-Bromo-benzylsulfanyl)-dimethylamino-methylene]-dimethyl-ammonium; iodide 

Downstream Products

• 63875-87-6 p-Brombenzyl-2-hydroxyethyldisulfid 
• 17742-50-6 2-(4-bromobenzylthio)acetic acid 
• 106-38-7 para-bromotoluene 
• 19829-56-2 4,4'-dibromobibenzyl 
• 433289-55-5 cis-N-Boc-4-(4-bromobenzyl thio)-L-proline 
• 29673-86-7 -benzyl-disulfid 
• 80813-32-7 5-(4-bromobenzylthiomethyl)-6-carbamoyluracil 
• 796739-73-6 3-(4-bromophenylmethylsulfanyl)-2,2-dimethylpropanoic acid methyl ester 
• 433289-54-4 Cis-4-(4-bromobenzyl thio)-L-proline Methyl Ester 
• 220666-28-4 [ReO(η(3)-(SCH2CH2)2S)(C6H4Br-4-CH2S)] 
• 1068660-70-7 3-(4-bromobenzylsulfanyl)-cyclohex-2-enone 
• 79-46-9 2-nitropropane 
• 1149523-88-5 C₇H₆BrNOS 
• 1174738-54-5 4-(4-bromobenzylsulfanyl)pyridine-2-carboxylic acid 

Relevant academic research and scientific papers

SULFUR EXTRUSION FROM DISULFIDES BY CARBENES

The present invention relates to a method for preparing a compound T having a thioether group from a compound D having a disulfide group in the presence of a carbene.

Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans

The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).

Benzylic Thio and Seleno Newman-Kwart Rearrangements

The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.

Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols

In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.

Preparation and in-vitro evaluation of 4-benzylsulfanylpyridine-2- carbohydrazides as potential antituberculosis agents

A set of 4-benzylsulfanylpyridine-2-carbohydrazides was synthesized and evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis, non-tuberculous mycobacteria, and multidrug-resistant M. tuberculosis. The activities expressed as the minimum inhibitory concentration (MIC) fall into a range of 2 to 125 μmol/L, most often 4 to 32 μmol/L. The results revealed that the substituents on the benzyl moiety do not influence the antimycobacterial efficacy. The substances exhibited similar activities against sensitive and resistant strains of M. tuberculosis. Furthermore, compounds show low antiproliferative effect and cytotoxicity.

Thioacetate deprotection

A method of thioacetate deprotection by providing a compound of the formula R1—S—CO—R2, and reacting the compound with a quaternary ammonium cyanide salt in the presence of a protic solvent in an inert atmosphere to convert the compound to a product of the formula R1—SH. R1 is an organic group in which the bonding to sulfur is through a saturated carbon, and R2 is an aliphatic group.

Mild and efficient methods for the conversion of benzylic bromides to benzylic thiols

Very mild and efficient methods are established for the conversion of the benzylic bromides at room temperature to their corresponding benzylic thiols with high yields (94-99%) in 1 h under N2.

Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide

A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols.

Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide func

One pot rapid synthesis of thiols from alcohols under mild conditions

Thiols are prepared in high yields from corresponding alcohols using Ph3P, NBS in acetone and followed by addition of polymer supported hydrosulfide under mild condition.