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| Benzhydrol Basic information |
| 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 | | form | Crystalline Solid | | pka | 13.55±0.20(Predicted) | | 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 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) |
| 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 | | 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 | | 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/v72-485Journal of the American Chemical Society, 55, p. 391, 1933 DOI: 10.1021/ja01328a057Tetrahedron 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.] |
| Benzhydrol Preparation Products And Raw materials |
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