68930-15-4

Basic information

• Product Name: 1-(benzyloxy)-1H-1,2,3-benzotriazole
• Synonyms: 1-(benzyloxy)-1H-1,2,3-benzotriazole
• CAS NO: 68930-15-4
• Molecular Formula: C₁₃H₁₁N₃O
• Molecular Weight: 225.24594
• Mol File: 68930-15-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(benzyloxy)-1H-1,2,3-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzyloxy)-1H-1,2,3-benzotriazole(68930-15-4)
• EPA Substance Registry System: 1-(benzyloxy)-1H-1,2,3-benzotriazole(68930-15-4)

Safety Data

• Hazardous Substances Data: 68930-15-4(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 62244-77-3 1-Hydroxy-1,2,3-benzotriazole potassium salt 
• 30223-22-4 S-benzyl-S-methyl-sulfodiimine 
• 2592-95-2 benzotriazol-1-ol 
• 21978-63-2 1H-benzo[d][1,2,3]triazol-1-yl 4-methanebenzenesulfonate 
• 100-51-6 benzyl alcohol 
• 42181-97-5 benzyl <(18)O> alcohol 
• 100-39-0 benzyl bromide 
• 108-88-3 toluene 

Downstream Products

• 95-14-7 1,2,3-Benzotriazole 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 62-53-3 aniline 
• 1227476-15-4 Azobenzene 
• 100-51-6 benzyl alcohol 
• 92-51-3 cyclohexylcyclohexane 
• 1821-36-9 N-phenyl-2-cyclohexylamine 
• 946-80-5 (benzyloxy)benzene 
• 140-29-4 phenylacetonitrile 

Relevant articles and documents

Highly symmetrical amino acid-derived N,N′-diacylated sulfodiimines

A mild and efficient method for the coupling of sulfodiimines with N-protected amino acids has been developed, yielding the corresponding N,N′-diacylated sulfodiimines with up to 94% yield.

Ultrasound accelerated synthesis of: O-alkylated hydroximides under solvent- A nd metal-free conditions

A novel, sustainable, environmentally friendly, high substrate scope, efficient, solvent-free and metal catalyst-free method for the cross-dehydrogenative coupling (CDC) reaction between N-hydroxyphthalimide (NHPI) and benzyl/ether compounds is described. This coupling reaction proceeds through ultrasound acceleration. Compared to conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions.

Facile synthesis of 1-Alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4- methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO- and AtO- produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO- is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd πallyl complexes by departure of BtO- has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.