5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole

Description

5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole is an intermediate in the synthesis of Losartan and Valsartan. Utilized for various purposes, 5-[4′-Bromomethyl-(1,1′-biphenyl)-2-yl]-1-triphenylmethyltetrazole has found application as a fluorescent probe to identify DNA damage. It serves as a photosensitizer in photodynamic therapy and acts as a catalyst in polymer synthesis. Furthermore, this compound functions as a fluorescent label to detect proteins and as a fluorescent indicator to detect metal ions.

Chemical properties

Off-White Solid

The Uses of 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole

5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole is an important pharmaceutical intermediate. It can be used in the preparation of olmesartan medoxomil key intermediates, Losartan potassium, Valsartan, Candesartan and molecular sieve catalysts.

Hazard

5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole has an acute toxin and is irritating to skin and eyes.

Synthesis

4-Methyl-2'-cyanobiphenyl is used as the raw material, and a cyclization reaction occurs with NaN3 (or Me3SiN3, Me3SnN3) in DMF or NMP solvent under the catalysis of Lewis acid ZnCl2 or triethylamine hydrochloride to generate (4'-methyl-1,1'-biphenyl-2-yl) tetrazole, which then reacts with trityl chloride to generate N-(triphenylmethyl)-5-(4'-methyl-1,1'-biphenyl-2-yl) tetrazole, and finally brominated in CCl4 or CH2Cl2 under the action of NBS, dibromohydantoin or bromine to generate 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole.

References

[1] HAI Z. Determination of the related substances in N-triphenylmethyl-5-(4’-bromomethylbiphenyl-2-yl-) terazole by HPLC[J]. West China Journal of Pharmaceutical Sciences, 2015.