392690-75-4

Basic information

• Product Name: (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole
• CAS NO: 392690-75-4
• Molecular Weight: 318.17
• Mol File: 392690-75-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole(392690-75-4)
• EPA Substance Registry System: (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole(392690-75-4)

Safety Data

• Hazardous Substances Data: 392690-75-4(Hazardous Substances Data)

Upstream product

• 591-20-8 3-Bromophenol 
• 95093-95-1 S-(+)-4-(oxiranylmethoxy)-9H-carbazole 
• 52602-39-8 9H-carbazol-4-ol 

Relevant articles and documents

Synthesis of Glycoborine, Glybomine A and B, the Phytoalexin Carbalexin A and the β-Adrenoreceptor Antagonists Carazolol and Carvedilol

We describe a regioselective synthesis of 4- or 5-substituted carbazoles by oxidative cyclisation of meta-oxygen-substituted N-phenylanilines. Using the regiodirecting effect of a pivaloyloxy group, we prepared 4-hydroxycarbazole, a precursor for the enantiospecific synthesis of the β-adrenoreceptor antagonists (?)-(S)-carazolol (5) and (?)-(S)-carvedilol (6). Regioselective palladium(II)-catalysed cyclisation of different diarylamines led to total synthesis of glycoborine (7) and the first total syntheses of the phytoalexin carbalexin A (8), glybomine A (9) and glybomine B (10). For glybomine B (10), a 5-hydroxycarbazole was converted into the corresponding triflate and utilized for introduction of a prenyl substituent.