|Jmol interactive 3D||Image
|Molar mass||108.14 g·mol−1|
|Density||1.044 g cm−3|
|Melting point||−15.2 °C (4.6 °F; 257.9 K)|
|Boiling point||205.3 °C (401.5 °F; 478.4 K)|
|3.50 g/100 mL (20 °C)
4.29 g/100 mL (25 °C)
|Solubility||soluble in benzene, methanol, chloroform, ethanol, ether, acetone|
|Vapor pressure||0.18 kPa (60 °C)|
Refractive index (nD)
|217.8 J/K mol|
Std enthalpy of
|Safety data sheet||External MSDS|
|Flash point||101 °C (214 °F; 374 K)|
|436 °C (817 °F; 709 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (Median dose)
|1250 mg/kg (rat, oral)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol is partially soluble in water (4 g/100 mL) and completely miscible in alcohols and diethyl ether.
- C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl
Like most alcohols, it reacts with carboxylic acids to form esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis. it will show SN2 mechanism. Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:
- C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2
Benzyl alcohol is used as a general solvent for inks, paints, lacquers, and epoxy resin coatings. Thus it can be used in paint strippers especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces. It is also a precursor to a variety of esters, used in the soap, perfume, and flavor industries. It is also used as a photographic developer.
Use in health care
Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics and topical drugs.
Benzyl alcohol has nearly the same refraction index of quartz and wool fibre. If a clear quartz object is immersed in benzyl alcohol, it becomes almost invisible. This test has been used to determine non-destructively whether an object is truly made of quartz (see crystal skull). Similarly, white wool immersed in benzyl alcohol also becomes almost invisible clearly revealing contaminants such as dark and medullated fibres and vegetable matter.
Benzyl alcohol is only a mild acute toxin with an LD50 of 1.2 g/kg in rats. It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.
Benzyl alcohol has been reported to cause skin allergy.
Benzyl alcohol is not considered to be a carcinogen and no data are available regarding teratogenic or reproductive effects.
- benzyl alcohol.
- The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 1138.
- The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
- Furuta, Kyoji; Gao, Qing-Zhi; Yamamoto, Hisashi (1995). "Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde". Org. Synth. 72: 86.; Coll. Vol. 9, p. 722.
- Parris, Chester L. (1962). "N-benzylacrylamide". Org. Synth. 42: 16.; Coll. Vol. 5, p. 73.
- Benzyl alcohol, chemicalland21.com.
- A. D. Wissner-Gross, "Dielectrophoretic reconfiguration of nanowire interconnects", Nanotechnology 17, 4986–4990 (2006).
- Nanowires get reconfigured, Nanotechweb.org, 19 October 2006.
- Prescribing Information for Ulesfia Lotion (PDF), Sciele Pharmaceuticals, Inc., April 2009, retrieved 2009-08-29.
- Friedrich Brühne; Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 7–8
- Carl R. Baum (2008), "Examples of mass exposures involving the pediatric population", in Jerrold B. Leikin; Frank P. Paloucek, Poisoning and Toxicology Handbook (4th ed.), Informa, p. 726
- Juan Gershanik; et al. (1982), "The gasping syndrome and benzyl alcohol poisoning.", N Engl J Med 307: 1384–8, doi:10.1056/nejm198211253072206
- EJ Curry; EM Warshaw (2005), "Benzyl alcohol allergy: importance of patch testing with personal products.", Dermatitis (16): 203–8
- Swarupa G Kulkarni; Harihara M Mehendale (2005), "Benzyl Alcohol", Encyclopedia of Toxicology 1 (2nd ed.), Elsevier, pp. 262–264
- International Chemical Safety Card 0833
- SIDS Initial Assessment Report for Benzoates from the Organisation for Economic Co-operation and Development (OECD)