Benzhydrol

Benzhydrol Basic information
Product Name:Benzhydrol
Synonyms:BENZHYDROL;HYDROXYDIPHENYL METHANE;Benzenemethanol,alpha-phenyl-;alpha-phenyl-benzenemethano;a-Phenylbenzenemethanol;a-Phenylbenzyl alcohol;DIPHENYLCARBINOL(BENZHYDROL);PARA-HYDROXYDIPHENYLMETHANE
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 Structure
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
pka13.55±0.20(Predicted)
color White to beige
Odorat 100.00 %. weedy green rose
Odor Typegreen
Water Solubility Slightly soluble in water.
Merck 14,1090
BRN 1424379
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, acids.
LogP2.670
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)
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
ToxicityLD50 orally in Rabbit: 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
MSDS Information
ProviderLanguage
Diphenylcarbinol English
SigmaAldrich English
ACROS English
ALFA English
Benzhydrol Usage And Synthesis
Chemical Propertiesoff-white powder
UsesAnchoring of carboxylic acids and alcohols
Uses
  1. 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.
  2. 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.
  3. Intermediate in the preparation of Modafinil (M482500).
DefinitionChEBI: 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.
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
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 DescriptionPharmaceutical 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 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.]
4',5'-DIBROMOFLUORESCEIN 3,3',5,5'-Tetrakis(trifluoromethyl)benzhydrol 97% 2,3,4,5,6-PENTAFLUOROBENZHYDROL Benzhydrol, 4,4'-dichloro-alpha-methyl- 2-AMINO-9-FLUORENOL BENZHYDROL, (DIPHENYLCARBINOL; DIPHENYL-METHANOL) Benzilic acid 4,4'-Bis(dimethylamino)thiobenzophenone DIPHENYLMETHANOL (BENZHYDROL) DIPHENHYDRAMINE HYDROCHLORIDE IMP. D (EP): DIPHENYLMETHANOL (BENZHYDROL) 1,1,3-Triphenylpropargyl alcohol 9-HYDROXYFLUORENE-9-CARBOXYLIC ACID ALPHA-NAPHTHOLBENZEIN Thymolphthalein Complexone PYROGALLOL RED 4-Methylbenzhydrol Benzhydrol, alpha-methyl- TETRAIODOPHENOLPHTHALEIN

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