3343-66-6

Usage

InChI:InChI=1/C11H12BrNO3S/c1-7(14)13-10(11(15)16)6-17-9-4-2-8(12)3-5-9/h2-5,10H,6H2,1H3,(H,13,14)(H,15,16)

Upstream product

• 68724-10-7 S-(4-bromo-phenyl)-cysteine 
• 108-24-7 acetic anhydride 
• 71-43-2 benzene 
• 68724-10-7 S-(p-bromophenyl)-L-cysteine 
• 616-91-1 N-acetylcystein 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 589-87-7 1,4-bromoiodobenzene 
• 75-36-5 acetyl chloride 
• 5429-56-1 N-Acetamidoacrylic acid 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 4775-80-8 (R)-2-acetamido-3-(phenylthio)propanoic acid 
• 68724-10-7 S-(4-bromo-phenyl)-cysteine 

Relevant academic research and scientific papers

Metal-free S-arylation of cysteine using arenediazonium salts

A mild chemoselective method for S-arylation of cysteine has been developed in an open-flask procedure under metal-free conditions using arenediazonium salts in methanol.

Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature

The third generation of aminobiphenyl palladacycle pre-catalyst “G3-Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.

Synthesis of Mercapturic Acid Derivatives of Putative Toxic Metabolites of Bromobenzene

The synthesis and characterization of nine isomerically defined S-arylmercapturic acids of interest in connection with the metabolism of the model hepatotoxin bromobenzene is described.Included are three S-(bromophenyl)-, two S-(bromohydroxyphenyl)-, and three S-(bromodihydroxyphenyl)mercapturic acids of defined substitution pattern.In addition, several related compounds with two or no bromine atoms are described.These syntheses depend on two basic methods, 1,4-addition of various arene thiols to acetamidoacrylic acid or the 1,4-addition of N-acetyl-L-cysteine to various benzoquinone derivatives.In addition, we describe a method for efficient conversion of the mercapturic acids to thioanisole derivatives, regioisomers of which can be separed and detected at low levels by capillary gas-liquid chromatography.