Benzyl Alcohol

Title: Benzyl Alcohol
CAS Registry Number: 100-51-6
CAS Name: Benzenemethanol
Additional Names: phenylcarbinol; phenylmethanol; a-hydroxytoluene
Molecular Formula: C7H8O
Molecular Weight: 108.14
Percent Composition: C 77.75%, H 7.46%, O 14.80%
Line Formula: C6H5CH2OH
Literature References: Constituent of jasmine, hyacinth, ylang-ylang oils, Peru and Tolu balsams, storax, where it occurs in ester form also. Originally prepd by the Cannizzaro reaction from benzaldehyde + KOH: Cannizzaro, Ann. 88, 129 (1853); cf. Hickinbottom, Reactions of Organic Compds. (Longmans, London, 3rd ed., 1957) p 251; A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 711; Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 193. Produced on a large scale by the action of sodium or potassium carbonate on benzyl chloride: DE 484662; Chem. Zentralbl. 1930, I, 1052; Frdl. 16, 426; cf. Kirk-Othmer Encyclopedia of Chemical Technology vol. 3 (Interscience, New York, 1964) pp 442-449. Toxicity: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).
Properties: Liquid. Faint aromatic odor. Sharp burning taste. d420 1.04535; d425 1.04156. mp -15.19°. bp760 204.7°; bp400 183.0°; bp200 160.0°; bp100 141.7°; bp60 129.3°; bp40 119.8°; bp20 105.8°; bp10 92.6°; bp5 80.8°; bp1.0 58.0°. nD20 1.54035; nD25 1.53837: Dreisbach, Martin, Ind. Eng. Chem. 41, 2875 (1941). Absorption spectrum: Brode, J. Phys. Chem. 30, 61 (1926). Vapor density 3.72 (air = 1.00). Flash pt, closed cup 213°F, open cup 220°F. Autoignition temp 817°F. One gram dissolves in about 25 ml water. One volume dissolves in 1.5 vols of 50% ethyl alcohol. Misc with abs and 94% alcohol, ether, chloroform. LD50 orally in rats: 3.1 g/kg (Smyth).
Melting point: mp -15.19°
Boiling point: bp760 204.7°; bp400 183.0°; bp200 160.0°; bp100 141.7°; bp60 129.3°; bp40 119.8°; bp20 105.8°; bp10 92.6°; bp5 80.8°; bp1.0 58.0°
Flash point: Flash pt, closed cup 213°F, open cup 220°F
Index of refraction: nD20 1.54035; nD25 1.53837: Dreisbach, Martin, Ind. Eng. Chem. 41, 2875 (1941)
Density: d420 1.04535; d425 1.04156
Toxicity data: LD50 orally in rats: 3.1 g/kg (Smyth)
Use: Manuf other benzyl compds. Pharmaceutic aid (antimicrobial). Solvent for gelatin, casein (when hot), solvent for cellulose acetate, shellac. Used in perfumery and in flavoring (mostly in form of its aliphatic esters). In microscopy as embedding material.
Therap-Cat-Vet: Has been used for relief from pruritis.
Benzyl Benzoate Benzyl Bromide Benzyl Chloride Benzyl Cinnamate Benzyl Cyanide

Benzyl alcohol
Benzyl alcohol
Benzyl alcohol
Identifiers
CAS number 100-51-6 YesY
PubChem 244
ChemSpider 13860335 YesY
UNII LKG8494WBH YesY
EC number 202-859-9
KEGG D00077 YesY
ChEBI CHEBI:17987 YesY
ChEMBL CHEMBL720 YesY
RTECS number DN3150000
Jmol-3D images Image 1
Image 2
Properties[1]
Molecular formula C7H8O
Molar mass 108.14 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
Solubility in water 3.50 g/100 mL (20 °C)
4.29 g/100 mL (25 °C)
Solubility soluble in benzene, methanol, chloroform, ethanol, ether, acetone
log P 1.10
Acidity (pKa) 15.40
Refractive index (nD) 1.5396
Viscosity 5.474 cP
Dipole moment 1.67 D
Thermochemistry
Std molar
entropy So298
217.8 J/K mol
Std enthalpy of
formation ΔfHo298
-352 kJ/mol
Hazards
MSDS External MSDS
EU Index 603-057-00-5
NFPA 704
NFPA 704.svg
1
1
0
Flash point 101 °C; 214 °F; 374 K
Autoignition temperature 436 °C; 817 °F; 709 K
Explosive limits 1.3-13%
LD50 1250 mg/kg (rat, oral)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.