PRODUCTS

BENZYL ALCOHOL

CAS Number: 100-51-6
EC Number: 202-859-9
Chemical formula: C7H8O
Preferred IUPAC name: Phenylmethanol

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.
Benzyl alcohol 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.

Natural occurrences
Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas.
Benzyl alcohol is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang.
Benzyl alcohol is also found in castoreum from the castor sacs of beavers.
Benzyl esters also occur naturally.

Preparation
Benzyl alcohol is produced industrially from toluene via benzyl chloride, which is hydrolyzed:

C6H5CH2Cl + H2O → C6H5CH2OH + HCl
Another route entails hydrogenation of benzaldehyde, a by-product of the oxidation of toluene to benzoic acid.

For laboratory use, Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol.
The latter also gives benzoic acid, an example of an organic disproportionation reaction.

Reactions
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.

Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide.
This is an example of a Ritter reaction:
C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2

Applications
Benzyl alcohol is used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings.
Thus benzyl alcohol can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.

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

Benzyl alcohol can be used as a local anesthetic, especially with epinephrine.

As a dye solvent, it enhances the process of dying wool, nylon, and leather.

Use in health care
Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics, and topical drugs.
Some caution is necessary if a high percent of Benzyl alcohol is used as benzaldehyde arises from benzyl alcohol when used as preservative in an injectable formulation solution.

Benzyl alcohol, sold under the brand name Ulesfia, was approved by the U.S. Food and Drug Administration (FDA) in 2009, as a 5% solution for the treatment of head lice in people 6 months of age and older.
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.

Contact dermatitis
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. Benzyl alcohol is a common ingredient in a variety of household products and can cause severe allergic contact dermatitis in a significant percentage of the population.

Safety
Benzyl alcohol has low acute toxicity with an LD50 of 1.2 g/kg in rats.
Benzyl alcohol 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.

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

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

Molar mass: 108.140 g·mol−1
Appearance: Colorless liquid
Odor: Slightly aromatic
Density: 1.044 g/cm3
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[vague]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
XLogP3: 1.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 1
Exact Mass: 108.057514874
Monoisotopic Mass: 108.057514874
Topological Polar Surface Area: 20.2 Å²
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 55.4
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Benzyl alcohol is being reviewed for use as a biocide in the EEA and/or Switzerland, for: product preservation.

Consumer Uses
Benzyl alcohol is used in the following products: washing & cleaning products, coating products, adhesives and sealants, polishes and waxes, inks and toners, air care products and perfumes and fragrances.
Benzyl alcohol has an industrial use resulting in manufacture of another substance (use of intermediates).
Other release to the environment of Benzyl alcohol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Article service life
Release to the environment of Benzyl alcohol can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal).
Other release to the environment of Benzyl alcohol is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Benzyl alcohol can be found in products with material based on: fabrics, textiles and apparel (e.g. clothing, mattress, curtains or carpets, textile toys), leather (e.g. gloves, shoes, purses, furniture), paper used for large surface area articles (e.g. construction and building materials for insulation panels, wall papers), paper (e.g. tissues, feminine hygiene products, nappies, books, magazines, wallpaper) and paper used for articles with intense direct dermal (skin) contact during normal use such as personal hygiene articles (e.g. nappies, feminine hygiene products, adult incontinence products, tissues, towels, toilet paper).

Widespread uses by professional workers
Benzyl alcohol is used in the following products: coating products, fillers, putties, plasters, modelling clay, metal surface treatment products, non-metal-surface treatment products and laboratory chemicals.
Benzyl alcohol is used in the following areas: building & construction work, health services, scientific research and development and formulation of mixtures and/or re-packaging.
Benzyl alcohol is used for the manufacture of: chemicals.
Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Uses at industrial sites
Benzyl alcohol is used in the following products: polymers, coating products, adhesives and sealants, fillers, putties, plasters, modelling clay, metal surface treatment products, non-metal-surface treatment products, washing & cleaning products, paper chemicals and dyes, lubricants and greases, photo-chemicals, textile treatment products and dyes, inks and toners and cosmetics and personal care products.
Benzyl alcohol is used in the following areas: building & construction work.
Benzyl alcohol is used for the manufacture of: chemicals, textile, leather or fur, pulp, paper and paper products, rubber products and plastic products.
Release to the environment of this substance can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and of substances in closed systems with minimal release.

Benzyl alcohol is most widely known as benzyl alcohol, the aromatic alcohol also goes by a few other names, such as benzenemethanol or phenylcarbinol.
Benzyl alcohol is derived from fruit, comes in the form of a colorless liquid, and has a slightly sweet scent.
As a multifunctional ingredient, you can spot benzyl alcohol on the ingredient label of many different skincare, cosmetic, and personal products, such as moisturizers, lip balms, face washes, and even makeup.
According to Wong, it's primarily used in product formulation as a preservative to stop microorganisms from overgrowing in products, which could later lead to an infection.

"Benzyl alcohol is mostly used because of the scaremongering about parabens," Wong says.
"Since a lot of consumers are worried about parabens, alternative preservatives have to be used for marketing reasons. It's found naturally, so companies can use it in products and still market them as 'natural.'"

Benefits of Benzyl Alcohol
Besides possibly having antioxidant effects in certain formulas, benzyl alcohol doesn't have any specific benefits for your skin itself, but rather helps to optimize skincare formulas so that they can better perform for your skin. Here are a few key ways benzyl alcohol helps your products work more effectively:

Preserves the product: According to Krant, benzyl alcohol acts as a preservative in skincare and cosmetic products due to its ability to kill microbes—especially parasites.
"Any cosmetic or personal care product that is made with no preservatives (for example, preservative-free eye drops) generally comes in individual single-use containers to prevent contamination by contact or air," she says. Benzyl alcohol allows products to be bottled in larger packages designed for more than one use.

Stabilizes the formula: Krant adds that the ingredient also acts as a stabilizing agent against the oxidative breakdown of the product, which means it allows your products to work more effectively for a longer period of time.

Has antioxidant activity: Krant says benzyl alcohol also has antioxidant properties, and antioxidants protect against free-radical damage.
Dissolves ingredients: Benzyl alcohol acts as a solvent and helps to dissolve other ingredients in a product's formula.
Decreases viscosity: Benzyl alcohol also decreases viscosity, which allows products to flow more easily.
Imparts a nice scent: As an aromatic alcohol, benzyl alcohol is naturally fragrant and gives off a slightly sweet scent.

Industries
Pharma
Lubricants
Water Treatment
Oil & Gas
Cleaning
Animal Nutrition
Coatings & Construction
Food and Nutrition
Agriculture
Cosmetics
Polymers
Rubber

Benzyl alcohol is an aromatic alcohol with the formula C7H8O.
The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH.
Benzyl alcohol is a colourless liquid with a mild pleasant aromatic odour.

Synonyms:
benzyl alcohol
phenylmethanol
benzenemethanol
100-51-6
phenylcarbinol
Benzoyl alcohol
benzylalcohol
Benzenecarbinol
Hydroxytoluene
Phenylmethyl alcohol
alpha-Toluenol
(Hydroxymethyl)benzene
Phenolcarbinol
Benzal alcohol
alpha-hydroxytoluene
benzylic alcohol
Alcool benzylique
Benzylicum
Methanol, phenyl-
Phenylcarbinolum
BENZYL-ALCOHOL
hydroxymethylbenzene
Phenyl-Methanol
Euxyl K 100
Bentalol
Aromatic alcohol
Caswell No. 081F
.alpha.-Toluenol
Benzyl alcohol (natural)
Alcool benzilico [DCIT]
Itch-X
alcoholum benzylicum
NCI-C06111
benzenmethanol
.alpha.-Hydroxytoluene
Benzylalkohol
FEMA No. 2137
Aromatic primary alcohol
Alcool benzylique [INN-French]
Benzyl alkohol
Alcohol bencilico [INN-Spanish]
Methanol benzene
Alcoholum benzylicum [INN-Latin]
UNII-LKG8494WBH
NSC 8044
HOCH-Ph-polymer
phenylmethan-1-ol
BnOH
MFCD00004599
Benzyl alcohol Natural
66072-40-0
TOLUENE,ALPHA-HYDROXY
LKG8494WBH
CHEBI:17987
NSC-8044
Hydroxymethyl resin (100-200 mesh)
NCGC00091865-01
Phenyl Methanol
DSSTox_CID_152
DSSTox_RID_75404
Benzyl alcohol, ACS reagent
Benzyl alcohol, for analysis
DSSTox_GSID_20152
MBN
Ulesfia
Alcool benzilico
Alcohol bencilico
CAS-100-51-6
HSDB 46
Ulesfia (TN)
CCRIS 2081
Benzyl alcohol [USAN:INN:JAN]
Benzyl alcohol, 98+%, Extra Dry, AcroSeal(R)
EINECS 202-859-9
EPA Pesticide Chemical Code 009502
BRN 0878307
enzylalcohol
BenzalalcoholBenzalcohol
Bentanol
Benzyl alcohol, polymer-bound
Benzyl alcohol, specified according to requirements of Ph.Eur.
Alcoolbenzylique
benzene-methanol
Benzyl Alcohole
a-Hydroxytoluene
a-Toluenol
AI3-01680
Benzyl alcohol [INN:JAN:NF]
OBZ
HOCH2-Ph-polymer
O[C]c1ccccc1
Sunmorl BK 20
Nat. Benzyl Alcohol
PhCH2OH
201740-95-6
Bn-OH
Benzyl alcohol-13C6
ACMC-1BQPG
SCHEMBL147
bmse000407
C6H5CH2OH
CHEMBL720
EC 202-859-9
WLN: Q1R
PINAPUR™ 9 BA-R
Benzyl alcohol (JP15/NF)
Benzyl alcohol, 99%, pure
$l^{1}-oxidanylmethylbenzene
4-06-00-02222 (Beilstein Handbook Reference)
BIDD:ER0248
TB 13G
Benzyl alcohol, LR, >=99%
Benzyl alcohol (Benzenemethanol)
DTXSID5020152
BDBM16418
INS NO.1519
NSC8044
Benzyl alcohol (JP17/NF/INN)
Benzyl Alcohol Reagent ACS Grade
HMS3264B16
HMS3885F10
Pharmakon1600-01502555
ZINC895302
Benzyl alcohol, analytical standard
Benzyl alcohol, AR, >=99.5%
HY-B0892
INS-1519
Benzyl alcohol, anhydrous, 99.8%
Tox21_111172
Tox21_202447
Tox21_300044
BBL011938
MFCD03792087
NSC760098
s4600
SBB058558
STL163453
Benzyl alcohol, >=99%, FCC, FG
AKOS000119907
AS04466
Benzyl alcohol, natural, >=98%, FG
CCG-213843
DB06770
Hydroxymethyl resin (200-400 mesh)
LS41488
MCULE-6011707909
NSC-760098
NCGC00091865-02
NCGC00091865-03
NCGC00091865-04
NCGC00254154-01
NCGC00259996-01
AK146334
Benzyl alcohol, ACS reagent, >=99.0%
Benzyl alcohol, ReagentPlus(R), >=99%
Benzyl alcohol, USP, 98.0-100.5%
I765
Benzyl alcohol on polystyrene, 3.5 mmol/g
B2378
Benzyl alcohol, tested according to Ph.Eur.
Benzylalcohol 100 microg/mL in Acetonitrile
E1519
FT-0622812
ST51028320
Benzyl alcohol, p.a., ACS reagent, 99.0%
Benzyl alcohol, SAJ first grade, >=98.5%
A14564
Benzyl alcohol, SAJ special grade, >=99.0%
Benzyl alcohol, Vetec(TM) reagent grade, 98%
C00556
C03485
D00077
Q52353
AB01563201_01
A800221
SR-01000872610
J-000153
SR-01000872610-3
F0001-0019
Z955123784
3762963D-6C2A-4BFF-AD94-3180E51BCA68
Benzyl alcohol, certified reference material, TraceCERT(R)
Benzyl alcohol, European Pharmacopoeia (EP) Reference Standard
Benzyl alcohol, puriss. p.a., ACS reagent, >=99.0% (GC)
Benzyl alcohol, United States Pharmacopeia (USP) Reference Standard
(Hydroxymethyl)polystyrene, 200-400 mesh, extent of labeling: ~1.7 mmol/g loading
(Hydroxymethyl)polystyrene, 200-500 mesh, extent of labeling: ~1.1 mmol/g loading
Benzyl alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Benzyl alcohol, PharmaGrade, USP/NF, Ph Eur, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production.
Benzyl alcohol, polymer-bound, 100-200 mesh, extent of labeling: 0.5-1.0 mmol/g loading, 1 % cross linked
Benzyl alcohol, polymer-bound, 100-200 mesh, extent of labeling: 1.0-2.0 mmol/g loading, 1 % cross-linked with divinylbenzene
Benzyl alcohol, polymer-bound, 70-90 mesh, extent of labeling: 0.5-1.0 mmol/g loading, 1 % cross-linked with divinylbenzene
Benzl alcohol, polymer-bound, 70-90 mesh, extent of labeling: 1.0-1.5 mmol/g loading, 1 % crosslinked
Benzyl alcohol, polymer-bound, 70-90 mesh, extent of labeling: 2.0-3.0 mmol loading, 1 % cross-linked
Benzyl alcohol, puriss., meets analytical specification of Ph.??Eur., BP, NF, 99-100.5% (GC)
StratoSpheres(TM) PL-HMS (Hydroxymethylstyrene) resin, 50-100 mesh, extent of labeling: 2.0 mmol loading, 1 % cross-linked