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Benzhydrol is widely used as intermediates in pharmaceuticals (including antihistamines), agrochemicals, perfumes and other organic compounds. It is used as a fixative in the perfume industry. It is involved in polymerization reaction as a terminating group. It is used as precursor to prepare modafinil, benztropine and diphehydramine.
The protection of OH groups as benzhydryl ethers can be catalyzed by sulfuric acid: Org. Synth. Coll., 4, 72 (1963); Angew. Chem. Int. Ed., 15, 281 (1976). See also Benzhydryl bromide, L02211. Thiols, e.g. in cysteine residues in peptide synthesis, can be protected as thioethers in the presence of TFA or HBr/AcOH: J. Chem. Soc. (C), 2683 (1970). The group can be cleaved by TFA in the presence of a cation scavenger, e.g. phenol or anisole (same ref.), or by Na in liquid NH3: J. Am. Chem. Soc., 84, 3887 (1962). See Appendix 6.
Carboxyl groups can be protected by esterification in benzene with tosic acid catalyst. Deprotection can be effected with the same catalyst by refluxing in toluene, which undergoes electrophilic alkylation: Tetrahedron Lett., 37, 1965 (1996).
Misawa, T.; Dodo, K.; Ishikawa, M.; Hashimoto, Y.; Sagawa, M.; Kizaki, M.; Aoyama, H. Structure-activity relationships of benzhydrol derivatives based on 1'-acetoxychavicol acetate (ACA) and their inhibitory activities on multiple myeloma cell growth via inactivation of the NF-κB pathway. Bioorg. Med. Chem. 2015, 23 (9), 2241-2246.
Taskin, O. S.; Temel, B. A.; Tasdelen, M. A.; Yagci, Y. Synthesis of block copolymers by selective H-abstraction and radical coupling reactions using benzophenone/benzhydrol photoinitiating system. Eur. Polym. J. 2015, 62, 304-311.
Gefahrenhinweise (EU): H303-H315-H319-H335
May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.