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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 has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Benzyl alcohol
Benzyl alcohol
Benzyl alcohol
IUPAC name
Other names
3D model (JSmol)
ECHA InfoCard 100.002.600
EC Number 202-859-9
E number E1519 (additional chemicals)
RTECS number DN3150000
Molar mass 108.140 g·mol−1
Appearance Colorless liquid
Odor Slightly aromatic
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 in other solvents Soluble[vague] in benzene, methanol, chloroform, ethanol, ether, acetone
log P 1.10
Vapor pressure 0.18 kPa (60 °C)
Acidity (pKa) 15.40
-71.83·10−6 cm3/mol
Viscosity 5.474 cP
1.67 D
217.8 J/K mol
-352 kJ/mol
P03AX06 (WHO)
Safety data sheet External MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
Flash point 93 °C (199 °F; 366 K)
436 °C (817 °F; 709 K)
Explosive limits 1.3–13%
Lethal dose or concentration (LD, LC):
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).
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Infobox references


Natural occurrencesEdit

Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang.[2] It is also found in castoreum from the castor sacs of beavers.[3]


Hydrolysis of benzyl chloride using sodium hydroxide is known as a salt elimination reaction:

C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl

Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde a second method.[citation needed]

Cannizzaro Reaction of benzaldehyde gives benzoic acid & benzyl alcohol in an apparent Redox.


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.[4]

Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:[5]



Benzyl alcohol is used as a general solvent for inks, waxes, shellacs, 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.[6]

It is a precursor to a variety of esters, used in the soap, perfume, and flavor industries. E.g. benzyl benzoate, benzyl salicylate, benzyl cinnamate, & Benzyl butyl phthalate .

It is also used in e-liquid for e-cigarettes to enhance the flavors used. When applied to damaged skin or mucous membranes at a 10% concentration, it acts as a local anesthetic and antimicrobial agent. It can be utilized as a degreaser in rug cleaning products. As a dye solvent, it enhances the process of dying wool, nylon, and leather.[7] It also has use as a photographic film developer, and as an insect repellent.

Nanotechnological usesEdit

Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires.[8][9]

Use in health careEdit

Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics, and topical drugs.

The use of benzyl alcohol as a 5% solution has been approved by the U.S. FDA for the treatment of head lice in children older than six months and in adults.[10] It affects the louse's spiracles, preventing them from closing. These then become clogged with water or mineral oil or other matter and cause the insect to die from asphyxiation.

Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.

Other usesEdit

Benzyl alcohol has nearly the same refraction index as quartz and wool fiber. 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 fibers and vegetable matter.

Contact dermatitisEdit

Illustration of allergic contact dermatitis

Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties. It is a common ingredient in a variety of household products and can cause severe allergic contact dermatitis in a significant percentage of the population.[11][12][13][14]


Benzyl alcohol has low acute toxicity with an LD50 of 1.2 g/kg in rats.[15] 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 is toxic to neonates, and is associated with the gasping syndrome.[16][17]

Benzyl alcohol is severely toxic and highly irritating to the eye.[15] Pure benzyl alcohol produces corneal necrosis.[18]

Benzyl alcohol is not considered to be a carcinogen and no data are available regarding teratogenic or reproductive effects.[15]


  1. ^ "Benzyl alcohol". Archived from the original on 2009-07-26.
  2. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 1138
  3. ^ Dietland Muller-Schwarze (2003). The Beaver: Its Life and Impact. p. 43.
  4. ^ 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". Organic Syntheses. 72: 86.; Collective Volume, 9, p. 722
  5. ^ Parris, Chester L. (1962). "N-benzylacrylamide". Organic Syntheses. 42: 16.; Collective Volume, 5, p. 73
  6. ^ Benzyl alcohol,, archived from the original on 2009-04-21, retrieved 2006-05-14
  7. ^ Michael Ash; Irene Ash (2004). Handbook of Preservatives. Synapse Info Resources. p. 292. ISBN 978-1-890595-66-1.
  8. ^ Alex Wissner-Gross (2006). "Dielectrophoretic reconfiguration of nanowire interconnects" (PDF). Nanotechnology. 17: 4986–4990. doi:10.1088/0957-4484/17/19/035.
  9. ^ Nanowires get reconfigured,, 19 October 2006, archived from the original on 28 October 2010, retrieved 29 August 2009
  10. ^ Prescribing Information for Ulesfia Lotion (PDF), Sciele Pharmaceuticals, Inc., April 2009, archived from the original (PDF) on 2017-08-09, retrieved 2009-08-29.
  11. ^ EJ Curry; EM Warshaw (2005), "Benzyl alcohol allergy: importance of patch testing with personal products.", Dermatitis (16): 203–8
  12. ^ "NACDG Allergen: Benzyl Alcohol - The Dermatologist".
  13. ^ "Benzyl Alcohol - Allergic Contact Dermatitis Database".
  14. ^ Fisher, A. A. (1 October 1975). "Allergic paraben and benzyl alcohol hypersensitivity relationship of the "delayed" and "immediate" varieties". Contact Dermatitis. 1 (5): 281–284. doi:10.1111/j.1600-0536.1975.tb05436.x. PMID 139248.
  15. ^ a b c Friedrich Brühne; Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 7–8
  16. ^ Carl R. Baum (2008), "Examples of mass exposures involving the pediatric population", in Jerrold B. Leikin; Frank P. Paloucek (eds.), Poisoning and Toxicology Handbook (4th ed.), Informa, p. 726
  17. ^ Juan Gershanik; et al. (1982), "The gasping syndrome and benzyl alcohol poisoning.", N Engl J Med, 307: 1384–8, doi:10.1056/nejm198211253072206, PMID 7133084
  18. ^ Swarupa G Kulkarni; Harihara M Mehendale (2005), "Benzyl Alcohol", Encyclopedia of Toxicology, 1 (2nd ed.), Elsevier, pp. 262–264

External linksEdit