134627-85-3

Upstream product

• 94-08-6 4-methylbenzoic acid ethyl ester 
• 29546-14-3 4-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N,N-dimethylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 

Downstream Products

• 2844-21-5 (E)-1-(4-methylphenyl)-2-(4-dimethylaminophenyl)-ethene 
• 300679-47-4 2-Benzotriazol-1-yl-2-(4-dimethylamino-phenyl)-1-p-tolyl-ethanol 

Relevant academic research and scientific papers

Benzotriazole-Mediated Stereoselective Olefination of Carboxylic Esters: Transformation of α-Amino Acid Esters into Chiral Allylamines

Diastereoselective trans-olefinations of carboxylic esters 3a-h have been accomplished using benzylic or allylic benzotriazole derivatives 1a-e to prepare α-(benzotriazol-1-yl) ketones 4a-i, for the subsequent reduction of 4a-i, and finally for low-valent titanium-effected dehydroxybenzotriazolylation.1 N-Protected α-amino acid esters 9a-c and 15 thus give allylamines 13a-e and 19 with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed.

Benzotriazole: A novel synthetic auxiliary

Benzotriazole and aldehydes react reversibly to give addition products: in the presence of amines and other NH-compounds water can be eliminated to form products of type Bt-CHR-NR′R″. The latter are versatile intermediates for the preparation of primary, secondary, and tertiary amines and in the alkylation of hydroxylamines, hydrazines, amides, thioamides, and sulfonamides. Polyfunctional amines and other polyfunctional compounds can also be prepared, and they enable significant extending of Mannich reaction. Similar oxygen compounds Bt-CRR′-OR″ enable new syntheses of ethers and esters. Reactions in which benzotriazole is eliminated rather than substituted open up new pathways to enamines, enol ethers, and nitrones. The methodology is capable of extension to a variety of vinylogous systems including benzenoid and heteroaromatic derivatives. In addition to acting as a versatile leaving group, benzotriazolyl residues activate neighboring CH bonds to proton loss and a variety of such applications is described.

Benzotriazole as a Synthetic Auxiliary: Advantageous Syntheses of Substituted Diarylmethanes and Heterocyclic Analogues

4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation.Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dy