Benzyl alcohol

Benzyl alcohol

Names
IUPAC name Phenylmethanol
Other names Phenylcarbinol
Identifiers
CAS Number	100-51-6 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:17987 Y
ChEMBL	ChEMBL720 Y
ChemSpider	13860335 Y
ECHA InfoCard	100.002.600
EC Number	202-859-9
E number	E1519 (additional chemicals)
KEGG	D00077 Y
PubChem	244
RTECS number	DN3150000
UNII	LKG8494WBH Y
InChI InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2 Y Key: WVDDGKGOMKODPV-UHFFFAOYSA-N Y InChI=1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2 Key: WVDDGKGOMKODPV-UHFFFAOYAH
SMILES c1ccc(cc1)CO c1ccc(cc1)CO
Properties
Chemical 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 in other solvents	Soluble in benzene, methanol, chloroform, ethanol, ether, acetone
log P	1.10
Vapor pressure	0.18 kPa (60 °C)
Acidity (pKa)	15.40
Magnetic susceptibility (χ)	-71.83·10−6 cm3/mol
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
Pharmacology
ATC code	P03AX06 (WHO)
Hazards
Safety data sheet	External MSDS
NFPA 704	1 1 0
Flash point	93 °C (199 °F; 366 K)
Autoignition temperature	436 °C (817 °F; 709 K)
Explosive limits	1.3–13%
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).
N  (what is YN ?)
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 has moderate solubility in water (4 g/100 mL) and miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

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. It is also found in castoreum from the castor sacs of beavers.

Benzyl alcohol is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:

It can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C₆H₅MgBr) with formaldehyde, followed by acidification.

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.