67592-77-2

Basic information

• Product Name: Silane, bromodimethyl(4-methylphenyl)-
• CAS NO: 67592-77-2
• Molecular Formula: C9H13BrSi
• Molecular Weight: 229.192
• Mol File: 67592-77-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Silane, bromodimethyl(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, bromodimethyl(4-methylphenyl)-(67592-77-2)
• EPA Substance Registry System: Silane, bromodimethyl(4-methylphenyl)-(67592-77-2)

Safety Data

• Hazardous Substances Data: 67592-77-2(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 75-78-5 dimethylsilicon dichloride 
• 2097-02-1 bis(4-methylphenyl)dimethylsilane 

Relevant articles and documents

Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone

Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.