Benzhydrol CAS:91-01-0

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Benzhydrol Basic information Product Name: Benzhydrol Synonyms: ALPHA-PHENYLBENZENEMETHANOL;BENZHYDROL;BENZOHYDROL;DIPHENYLCARBINOL;DIPHENYLMETHANOL;HYDROXYDIPHENYL METHANE;Benzenemethanol,alpha-phenyl-;Benzhydryl alcohol CAS: 91-01-0 MF: C13H12O MW: 184.24 EINECS: 202-033-8 Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Intermediates;Benzhydrols, Benzyl & Special Alcohols;API intermediates;Pharmaceutical Intermediates;bc0001 Mol File: 91-01-0.mol 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) Fp  160 °C storage temp.  Store below +30°C. solubility  0.52g/l insoluble pka 13.55±0.20(Predicted) form  Crystalline Solid color  White to beige Odor at 100.00 %. weedy green rose Odor Type green Water Solubility  Slightly soluble in water. Merck  14,1090 BRN  1424379 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, acids. LogP 2.670 CAS DataBase Reference 91-01-0(CAS DataBase Reference) NIST Chemistry Reference Benzenemethanol, «alpha»-phenyl-(91-01-0) EPA Substance Registry System Benzenemethanol, .alpha.-phenyl- (91-01-0) Safety Information Hazard Codes  Xi Risk Statements  36/37/38 Safety Statements  26-36-24/25 WGK Germany  2 RTECS  DC7452000 Hazard Note  Irritant TSCA  Yes HS Code  29062900 Toxicity LD50 orally in Rabbit: 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg Benzhydrol Usage And Synthesis Chemical Properties off-white powder or White or colorless crystals. M.P. 69℃. B.p. 281℃. Practically insoluble in water, soluble in alcohol, miscible with oils. The crystals have a very faint musty-rosy odor, somewhat similar to that of Benzophenonc and Trichloromethyl phenyl carbinyl acetate. Uses 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). Uses Anchoring of carboxylic acids and alcohols Definition ChEBI: Diphenylmethanol is a secondary alcohol that is diphenylmethane which carries a hydroxy group at position 1. It has a role as a rat metabolite, a bacterial xenobiotic metabolite, a human xenobiotic metabolite and a human urinary metabolite. It is a secondary alcohol and a member of benzyl alcohols. It derives from a hydride of a diphenylmethane. Preparation By reduction of Benzophenone, e.g. with zinc in aqueous alkali. Reactions Benzhydrol 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 General Description Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards Purification Methods Crystallise 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.] Toxics Screening Level The ITSL for Benzhydrol has been set at 16 μg/m3 based on annual average time. Benzhydrol Preparation Products And Raw materials Raw materials ZINC-->Benzophenone-->(Trimethylsiloxy)diphenylmethane-->2H-Pyran, 2-(diphenylmethoxy)tetrahydro--->TRIMETHYL(PHENYL)TIN-->2,4,6-Triphenylboroxin-->Diphenylmethane-->Diphenhydramine-->Bromodiphenylmethane Preparation Products Indigo Carmine-->3-Methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene-->1-BENZHYDRYLPIPERAZINE-->2-Chlorotrityl chloride-->CLOTRIMAZOLE IMP. A (PHARMEUROPA): (2-CHLOROPHENYL)DIPHENYLMETHANOL-->ERIO GREEN B-->1,1',1'',1'''-(Oxydimethylidyne)Tetrakis Benzene-->BENZHYDRYL ACETATE-->benzhydryl thiocyanate-->Stearoylbenzoylmethane



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