3393-00-8

Basic information

• Product Name: 4-bromo-4'-methylsulfanyl-biphenyl
• Synonyms: 4-bromo-4'-methylsulfanyl-biphenyl
• CAS NO: 3393-00-8
• Molecular Formula: C₁₃H₁₁BrS
• Molecular Weight: 279.19544
• Mol File: 3393-00-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 371.6 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: /
• Density: 1.44 g/cm³
• CAS DataBase Reference: 4-bromo-4'-methylsulfanyl-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-4'-methylsulfanyl-biphenyl(3393-00-8)
• EPA Substance Registry System: 4-bromo-4'-methylsulfanyl-biphenyl(3393-00-8)

Safety Data

• Hazardous Substances Data: 3393-00-8(Hazardous Substances Data)

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 624-92-0 Dimethyldisulphide 
• 92-86-4 4-(4-bromophenyl)bromobenzene 

Downstream Products

• 220805-21-0 4'-bromo-4-mercaptobiphenyl 
• 875272-89-2 (S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid 
• 501944-48-5 C₁₃H₁₃BO₂S 
• 82955-03-1 2-(4-(methylthio)phenyl)adamantan-2-ol 

Relevant articles and documents

The Alkyne Moiety as a Latent Electrophile in Irreversible Covalent Small Molecule Inhibitors of Cathepsin K

Irreversible covalent inhibitors can have a beneficial pharmacokinetic/pharmacodynamics profile but are still often avoided due to the risk of indiscriminate covalent reactivity and the resulting adverse effects. To overcome this potential liability, we introduced an alkyne moiety as a latent electrophile into small molecule inhibitors of cathepsin K (CatK). Alkyne-based inhibitors do not show indiscriminate thiol reactivity but potently inhibit CatK protease activity by formation of an irreversible covalent bond with the catalytic cysteine residue, confirmed by crystal structure analysis. The rate of covalent bond formation (kinact) does not correlate with electrophilicity of the alkyne moiety, indicative of a proximity-driven reactivity. Inhibition of CatK-mediated bone resorption is validated in human osteoclasts. Together, this work illustrates the potential of alkynes as latent electrophiles in small molecule inhibitors, enabling the development of irreversible covalent inhibitors with an improved safety profile.

Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

A selective metal-halogen exchange/electrophilic quench protocol on 4,4′-dibromobiphenyl 4 that proceeds under non-cryogenic conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor.