ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Aromatic alcohol > Benzhydrol
Benzhydrol Chemical Properties
- Melting point:65-67 °C (lit.)
- Boiling point:297-298 °C (lit.)
- Density 1.0120 (rough estimate)
- vapor pressure 0.000076 hPa (20 °C)
- refractive index 1.5727 (estimate)
- Flash point:160 °C
- storage temp. Store below +30°C.
- solubility 0.52g/l insoluble
- form Crystalline Solid
- color White to beige
- Water Solubility Slightly soluble in water.
- Merck 14,1090
- BRN 1424379
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, acids.
- CAS DataBase Reference91-01-0(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzenemethanol, «alpha»-phenyl-(91-01-0)
- EPA Substance Registry SystemBenzenemethanol, .alpha.-phenyl- (91-01-0)
Benzhydrol Usage And Synthesis
- Chemical Propertiesoff-white powder
- Benzhydrols are industrially important compounds. On oxidation Benzhydrols yields Benzophenone, which are useful synthones for fullerenes, bioactive oxygen heterocycles, dyes and medicines. Various Cr (VI) and other oxidizing agents are used for oxidizing benzhydrol.
- 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.
- Intermediate in the preparation of Modafinil (M482500).
- ReactionsBenzhydrol is oxidized to benzophenone, by sodium hypochlorite (commonly known as bleach) in the presence of a phase-transfer catalyst.
Synthesis: In a 20-mL green capped vial, place 1.5 mL of ethyl acetate, 100 mg (0.54 mmol) of benzhydrol and a few drops of methyltricaprylammonium chloride solution (Stark's catalyst or tricaprylmethylammonium chloride). Add a half-inch magnetic stirring bar, and stir until all reagents are dissolved. Cool the solution in an ice bath and add 2 mL of 5% NaOCl (aq) (bleach) dropwise using a 2.5- mL syringe. After the addition of the hypochlorite is complete, allow the reaction to stir for five minutes in the ice-water bath and then stir for a period of one hour at room temperature.
Reduction of benzophenone to benzhydrol.
4MPDC (4-Methyl pyridinium di chromate) is used as oxidizing agent to oxidize benzhydrol. PDC is a mild and selective oxidizing agent and is soluble in water and many organic solvents. Therefore, advantage over inorganic dichromate.
- Synthesis Reference(s)Canadian Journal of Chemistry, 50, p. 3058, 1972 DOI: 10.1139/v72-485
Journal of the American Chemical Society, 55, p. 391, 1933 DOI: 10.1021/ja01328a057
Tetrahedron Letters, 29, p. 139, 1988 DOI: 10.1016/S0040-4039(00)80036-2
- Purification MethodsCrystallise benzhydrol from hot H2O or pet ether (b 60-70o), pet ether containing a little *benzene, from CCl4, or EtOH (1mL/g). An additional purification step includes passage of a *benzene solution through an activated alumina column. It sublimes in a vacuum. Also recrystallise it three times from MeOH/H2O [Naguib J Am Chem Soc 108 128 1986]. [Beilstein 6 IV 4648.]
Benzhydrol Preparation Products And Raw materials
- Diphenylsilanediol 4'-tert-Butylacetophenone 4'-tert-Butyl-4-chlorobutyrophenone ERYTHROSIN B 4,4'-Difluorobenzhydrol 4',5'-DIBROMOFLUORESCEIN Benzilic acid Methyl benzilate 4,4'-Dichlorobenzhydrol 1,1,3-Triphenylpropargyl alcohol ALPHA-NAPHTHOLBENZEIN o-Methyl benzhydrol 9-HYDROXYFLUORENE-9-CARBOXYLIC ACID TETRAIODOPHENOLPHTHALEIN DIBENZOSUBERENOL 4-Methylbenzhydrol Thymolphthalein Complexone Benzhydrol, alpha-methyl-
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