15960-81-3

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL BROMOMETHYL SULFIDE is used as a key intermediate in the synthesis of pharmaceutical products for the development of inhibitors and anticancer compounds. Its role in the creation of these medications is vital due to its unique chemical properties, which allow for the formation of new bonds and reactions necessary for the production of effective drugs.
Used in Anticancer Applications:
BENZYL BROMOMETHYL SULFIDE is used as a component in the preparation of potent, orally active inhibitors of carboxypeptidase U (TAFIa). These inhibitors have potential applications in the treatment of cancer, as they can help regulate the activity of enzymes involved in tumor growth and progression.

Upstream product

• 3970-13-6 benzyl chloromethyl sulfide 
• 50-00-0 formaldehyd 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 52756-18-0 2-((benzylthio)methyl)dodecanoic acid 
• 52756-17-9 3-(benzylthio)-2-phenylpropionic acid 
• 52756-20-4 2-((benzylthio)methyl)cyclooctanone 
• 95798-35-9 (4S)-3-<(2S)-1-oxo-2-<<(phenylmethyl)thio>methyl>-3-phenylpropyl>-4-(1-methylethyl)-2-oxazolidinone 
• 142542-55-0 3-<1-oxo-2(S)-<<(phenylmethyl)thio>methyl>butyl>-4(S)-(1-methylethyl)-2-oxazolidinone 
• 95798-32-6 (4R,5S)-3-<(2R)-1-oxo-2-<<(phenylmethyl)thio>methyl>-3-phenylpropyl>-4-methyl-5-phenyl-2-oxazolidinone 
• 155896-57-4 (4S)-3-<(2S,3S)-1-oxo-2-<<(2-phenylethyl)thio>methyl>-3-phenylbutyl>-4-(1-methylethyl)-2-oxazolidinone 
• 155779-81-0 (4S)-3-<(2S,3R)-1-oxo-2-<<(2-phenylethyl)thio>methyl>-3-phenylbutyl>-4-(1-methylethyl)-2-oxazolidinone 
• 178377-76-9 methyl 5-benzylthio-3-oxopentanoate 
• 950672-58-9 (RS)-2-benzylsulfanylmethyl-2-methylmalononitrile 
• 256505-79-0 diethyl 2-(benzylthiomethyl)-2-methylmalonate 
• 950672-73-8 S-benzyl-α-methyl-L-cysteine hydrochloride 
• 138165-80-7 2-[[(Phenylmethyl)thio]methyl]-4,4,4-trifluorobutyric acid 
• 103003-94-7 2-Phenyl-3-phenylmethanesulfinyl-propionic acid 

Relevant academic research and scientific papers

An expeditious and efficient bromomethylation of thiols: Enabling bromomethyl sulfides as useful building blocks

A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.

Organoselenium Chemistry. Alkylation of Acid, Ester, Amide, and Ketone Enolates with Bromomethyl Benzyl Selenide and Sulfide: Preparation of Selenocysteine Derivatives

Bromomethyl benzyl selenide has been prepared and used for the alkylation of several carboxylic acid and amide dianions and certain ketones and ester enolates.Clean reaction could not be achieved for ketones and esters whose alkylation products were subject to selenolate elimination.The selenide reacted 18 times more slowly than bromomethyl benzyl sulfide, which alkylated ketones in fair yield even in some cases where the selenide failed.The bromomethyl benzyl sulfide alkylation products gave α-methylene ketones upon oxidation to sulfoxide and thermolysis.Several protected amino acid enolates (valine, alanine, and glycine) were alkylated with bromomethyl benzyl selenide.The product from glycine, 5b, was converted to the protected dehydroalanine 11 by oxidation and to the protected selenocysteine 10 by using bromine cleavage of the benzyl selenide.Halogen reagents (Br2, SO2Cl2) were shown to very efficiently and generally convert benzyl selenides to selenenyl halides, which were converted to diselenides or selenides by reduction or alkylation.