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Benzhydryl bromide, 90+%, Thermo Scientific Chemicals
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Catalog number L02211.22
also known as L02211-22
Price (USD)/ Each
68.30
-
Quantity:
100 g
Price (USD)/ Each
68.30
Benzhydryl bromide, 90+%, Thermo Scientific Chemicals
Catalog numberL02211.22
Price (USD)/ Each
68.30
-
Chemical Identifiers
CAS776-74-9
IUPAC Name[bromo(phenyl)methyl]benzene
Molecular FormulaC13H11Br
InChI KeyOQROAIRCEOBYJA-UHFFFAOYSA-N
SMILESBrC(C1=CC=CC=C1)C1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetIdentification (FTIR)Conforms
Appearance (Color)Cream to yellow to orange to red to brown
Assay (GC)≥90.0%
FormCrystals or powder or crystalline powder or lumps or fused solid
Melting Point (clear melt)31.0-44.0?C
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Insoluble in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents and bases. It is sensitive to moisture. Protect from humidity and water. Store under dry inert gas.
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.
Solubility
Insoluble in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents and bases. It is sensitive to moisture. Protect from humidity and water. Store under dry inert gas.
RUO – Research Use Only
General References:
- 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.