153529-51-2

Basic information

• Product Name: [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester
• Synonyms: [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester
• CAS NO: 153529-51-2
• Molecular Weight: 354.409
• Mol File: 153529-51-2.mol

Chemical Properties

• CAS DataBase Reference: [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester(153529-51-2)
• EPA Substance Registry System: [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester(153529-51-2)

Safety Data

• Hazardous Substances Data: 153529-51-2(Hazardous Substances Data)

Upstream product

• 21978-58-5 7-methyl-benzotriazol-1-ylamine 
• 100-52-7 benzaldehyde 
• 153529-47-6 1-(tert-butyloxycarbonylamino)-7-methylbenzotriazole 
• 153529-46-5 1-[Bis(tert-butoxycarbonyl)amino]-7-methylbenzotriazole 

Downstream Products

• 153529-60-3 7-(2'-hydroxy-2'-phenylethyl)-1H-benzotriazol-1-amine 

Relevant articles and documents

Directed deprotonation of 7-methyl-1-aminobenzotriazole: An approach to ortho-substituted benzyne precursors

Lateral deprotonation of N-Boc-1-amino-7-methylbenzotriazole 7 using BuLi-TMEDA leads to the synthetically useful dianion 18, which can be alkylated and which condenses smoothly with a range of aldehydes, ketones and epoxides to provide derivatives (19, 20 and 21 respectively), which are potentially useful in the generation of substituted benzynes.

A route to ortho-substituted benzyne precursors by deprotonation of 7-methyl-1-aminobenzotriazole derivatives

Double deprotonation of N-Boc-7-methyl-1-aminobenzotriazole 6 using (n)BuLi-TMEDA-THF [-78°C -> 0°C) results in an essentially quantitative conversion to the dianionic intermediate 7. Trapping at the carbon-centred anion occurs selectively under suitable conditions with alkylating agents, aldehydes and ketones to give good the excellent yields of the 7-substituted-1-aminobenzotriazoles 8-15, precursors of ortho-substituted benzynes.