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Benzhydryl bromide is a halogenated building block. Benzhydryl group was preferred to the commoner benzyl to protect 2-nitrophenol in the Bartoli (vinyl Grignard) synthesis of 7-hydroxyindole. Protection was by reaction with the phenol in the presence of potassium carbonate in acetone; deprotection of the indole was by hydrogenolysis.
S. Winstein.; Arnold H. Fainberg.; E. Grunwald. Correlation of Solvolysis Rates. VIII. Benzhydryl Chloride and Bromide. Comparison of mY and Swain's Correlations. J. Am. Chem. Soc. 1957, 79 (15), 4146-4155.
Anu Mahadevan.; Howard Sard.; Mario Gonzalez.; John C. McKew. A general method for C3 reductive alkylation of indoles. Tetrahedron Letters. 2003, 44(24), 4589-4591.
The benzhydryl group was preferred to the commoner benzyl to protect 2-nitrophenol in the Bartoli (vinyl Grignard) synthesis of 7-hydroxyindole. Protection was by reaction with the phenol in the presence of potassium carbonate in acetone; deprotection of the indole was by hydrogenolysis: Synth. Commun., 21, 611 (1991).
Compare also Benzhydrol, A12884.
Hazard Statements: H314-H335
Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant