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BENZENEMETHANOL

CAS Number: 100-51-6
Molecular Weight: 108.14
Beilstein: 878307
EC Number: 202-859-9
Molecular Formula: C7H8O or C6H5CH2OH

APPLICATIONS


Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Benzenemethanol is used as a preservative in pharmaceutical preparations in concentration up to 2% and as a solubilizer in concentrations of 5%.
Moreover, Benzenemethanol is effective against gram-positive organisms.

Benzenemethanol may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by chromatography and spectrophotometry.
These Secondary Standards are qualified as Certified Reference Materials.
These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

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

Benzenemethanol is a precursor to a variety of esters and ethers, used in the soap, perfume, and flavor industries.
Some of these are benzyl benzoate, benzyl salicylate, benzyl cinnamate, dibenzyl ether, benzyl butyl phthalate.

Benzenemethanol can be used as a local anesthetic, especially with epinephrine.
As a dye solvent,Benzenemethanol enhances the process of dying wool, nylon, and leather.

Uses of Benzenemethanol in health care:

Benzenemethanol 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 Benzenemethanol is used as benzaldehyde arises from Benzenemethanol when used as preservative in an injectable formulation solution.

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

Contact dermatitis:

Benzenemethanol 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.
More to that, Benzenemethanol is a common ingredient in a variety of household products and can cause severe allergic contact dermatitis in a significant percentage of the population.

Benzenemethanol is used as a local anesthetic.
Also, Benzenemethanol is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.


Uses of Benzenemethanol:

Arts and crafts/office supplies
Body paint
Products placed on the skin for decorative purposes (body paints, markers, glitters, play cosmetics, Halloween cosmetics, and products such as henna)
General arts and crafts supplies
Arts and crafts supplies which can not be assigned to a more refined category
Home and office products
Pens and markers
Writing utensils containing liquid or gel ink
Active oral pain reliever
Antimicrobial
Binder
Biocide
Chemical synthesis
Cleaning agent
Cleaning and safety
Products used for cleaning or safety in an occupational or industrial setting
Air freshener
Home air fresheners, including candles with a fragrance    
Bathroom cleaner
Glass cleaner
Products used to clean glass, mirrors, and windows
General household cleaning
Surface cleaner
Products used to clean hard surfaces in the home, including kitchen specific hard surface cleaners    
Heavy duty cleaner
Heavy duty hard surface cleaning products that may require dilution prior to use (i.e., may be concentrated)    
Coalescents
Contains fragrance allergens
Curing agent component
Diluent
Emulsifier/preservative
External analgesic
Flavoring agent or adjuvant
Fragrance
Home maintenance
Adhesive and adhesive remover related products
Multipurpose adhesive
General purpose repair adhesives including all purpose glues, super glue, and epoxies; not including wood glues
Caulk/sealant
Liquid or gels designed to seal cracks or fill cracks and depressions on hard surfaces
Paint/stain and related products
Paint or stain related products
Home improvement paints, excluding or not specified as oil-, solvent-, or water-based paints
Paint cleaner
Paint removing products for clean-up
Stripper
Products applied to hard surfaces to remove paints and finishes
Water-based paint
Bite relief
Products applied to the skin for soothing insect bites
Body care set
Multicomponent body care or bath set for which individual products are not designated
Products related to body hygiene which do not fit into a more refined category    Product Use Category (PUC)
Bar and other solid soaps
Body cleaners containing abrasives or exfoliants
Body cleaners, washes, shower gels
Hand soap
Body oil
Lipophilic products applied to skin (excluding baby oils)
Baby lotion
Baby cream or lotion (excluding diaper creams)
Baby wipes
Textile wipes and towelettes specifically marketed for use on infants
Antiseptic and dental mouthwashes and rinses
Toothpastes and dentrifices
Deodorants and antiperspirants
Eye care and contacts
Products applied to skin located around the eye to moisturize or improve skin qualities
Facial cleansing and moisturizing
Face cream/moisturizer
Moisturizers, lotions, and creams for treating the face (excluding eye-specific products)
Facial cleansing and moisturizing
Leave-on masks or peels for treatment of the face
Fragrances, colognes, and perfumes
General moisturizing products
Hand/body lotion
Products specifically marketed for application to hands or body to moisturize or improve skin characteristics (excluding baby lotion)

Industry Uses:

Adhesives and sealant chemicals
Agricultural chemicals (non-pesticidal)
Dyes
Functional fluids (closed systems)
Intermediates
Laboratory chemicals
Medical / pharmaceutical
Medical/pharmaceutical, flavor/fragrance, food and beverage/preservative, intermediates, photochemicals
Odor agents
Paint additives and coating additives not described by other categories
Plasticizers
Process regulators
Processing aids, not otherwise listed
Repackaged only in industrial context, substance is commercially used as an epoxy constituent.
Solvents (for cleaning and degreasing)


Consumer Uses:

Adhesives and sealants
Agricultural products (non-pesticidal)
Air care products
Automotive care products
Building/construction materials not covered elsewhere
Chemical manufacturing
Cleaning and furnishing care products
Electrical and electronic products
Epoxy resins
Floor Care Chemicals
Industrial Manufacturing
Ink, toner, and colorant products
Laundry and dishwashing products
Non-TSCA use
Paints and coatings
Personal care products
Photographic supplies, film, and photo chemicals
Plastic and rubber products not covered elsewhere
Aroma chemicals

Benzenemethanol is used as a preservative, epoxy resin catalyst, and in the photographic developer C-22.
Further, Benzenemethanol is used as a preservative, solvent, and local anesthetic.
Benzenemethanol is used as a preservative in drugs for injection.

Benzenemethanol is used in flavors and perfumes and as a solvent for inks and dyes.

DESCRIPTION


Benzenemethanol is an aromatic alcohol with the formula C6H5CH2OH.
Furthermore, Benzenemethanol is a colorless liquid with a mild pleasant aromatic odor.
Benzenemethanol is a useful solvent due to its polarity, low toxicity, and low vapor pressure.

Benzenemethanol 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 of Benzenemethanol:
Benzenemethanol is produced naturally by many plants and is commonly found in fruits and teas.

Moreover, Benzenemethanol is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang.
Benzenemethanol is also found in castoreum from the castor sacs of beavers.

Preparation of Benzenemethanol:

Benzenemethanol 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 Benzenemethanol.
The latter also gives benzoic acid, an example of an organic disproportionation reaction.

Benzenemethanol appears as a clear colorless liquid with a pleasant odor.
Nonetheless, Benzenemethanol is lightly denser than water.

Flash point of Benzenemethanol is 194 °F.
Boiling point of Benzenemethanol is 401 °F.

Contact may irritate skin, eyes, and mucous membranes.
Benzenemethanol may be slightly toxic by ingestion.
Furthermore, Benzenemethanol can be used to make other chemicals.

Benzenemethanol is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
Further to that, Benzenemethanol has a role as a solvent, a metabolite, an antioxidant and a fragrance.
Benzyl alcohol is a Pediculicide.

PROPERTIES


Chemical formula: C7H8O
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

Molecular Weight: 108.14
XLogP3: 1.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 
Exact Mass: 108.057514874
Monoisotopic Mass: 108.057514874
Topological Polar Surface Area: 20.2 Ų
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

SAFETY


Benzenemethanol has low acute toxicity with an LD50 of 1.2 g/kg in rats.
Furthermore, Benzenemethanol oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid.

Very high concentrations of Benzenemethanol can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.
Benzenemethanol is toxic to neonates and is associated with the gasping syndrome.

Benzenemethanol is severely toxic and highly irritating to the eye.
Pure Benzenemethanol produces corneal necrosis.

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

SYNONYMS


Benzyl alcohol, α-methyl-; α-Methylbenzyl alcohol; α-Phenethyl alcohol; α-Phenylethanol; α-Phenylethyl alcohol; (1-Hydroxyethyl)benzene; Ethanol, 1-phenyl-; Methylphenylcarbinol; Phenylmethylcarbinol; Styralyl alcohol; 1-Phenethyl alcohol; 1-Phenyl-1-hydroxyethane; 1-Phenylethanol; 1-Phenylethyl alcohol; sec-Phenethyl alcohol; dl-α-Methylbenzyl alcohol; Methanol, methylphenyl-; NCI-C55685; 1-Fenylethanol; Fenyl-methylkarbinol; Styrallyl alcohol; UN 2937; α-Methylbenzenemethanol; α-Hydroxyethylbenzene; NSC 25502; (S)-α-Methyl-benzenemethanol; alcohol methyl benzylic

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
hydroxymethylbenzene
Phenyl-Methanol
BENZYL-ALCOHOL
Euxyl K 100
Bentalol
Aromatic alcohol
66072-40-0
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]
NSC 8044
HOCH-Ph-polymer
BnOH
Benzyl alcohol, polymer-bound
Benzyl alcohol Natural
MFCD00004599
Hydroxymethyl resin (100-200 mesh)
TOLUENE,ALPHA-HYDROXY
LKG8494WBH
CHEBI:17987
NSC-8044
Hydroxymethyl resin (200-400 mesh)
NCGC00091865-01
Phenyl Methanol
DSSTox_CID_152
DSSTox_RID_75404
DSSTox_GSID_20152
185532-71-2
MBN
Ulesfia
Alcool benzilico
Alcohol bencilico
phenylmethan-1-ol
CAS-100-51-6
HSDB 46
Ulesfia (TN)
CCRIS 2081
Benzyl alcohol [USAN:INN:JAN]
EINECS 202-859-9
UNII-LKG8494WBH
EPA Pesticide Chemical Code 009502
BRN 0878307
enzylalcohol
Benzalalcohol
Benzalcohol
Bentanol
Alcoolbenzylique
Alcohol,benzyl
benzene-methanol
Benzyl Alcohole
a-Hydroxytoluene
a-Toluenol
AI3-01680
Benzyl alcohol [INN:JAN:NF]
Alcohol benzylicus
HOCH2-Ph-polymer
Sunmorl BK 20
Nat. Benzyl Alcohol
PhCH2OH
201740-95-6
Bn-OH
Benzyl alcohol-13C6
SCHEMBL147
Benzyl alcohol, ACS grade
bmse000407
C6H5CH2OH
CHEMBL720
EC 202-859-9
WLN: Q1R
PINAPUR™ 9 BA-R
Benzyl alcohol (JP15/NF)
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
STL163453
Benzyl alcohol, >=99%, FCC, FG
AKOS000119907
Benzyl alcohol, natural, >=98%, FG
Benzylalcohol 100 microg/mL in Methanol
NCGC00091865-02
NCGC00259996-01
Benzyl alcohol, ACS reagent, >=99.0%
Benzyl alcohol, ReagentPlus(R), >=99%
Benzyl alcohol, USP, 98.0-100.5%
Benzylalcohol 1000 microg/mL in Ethanol
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
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%
D70182
E-1519
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
Benzyl alcohol, polymer-bound, 70-90 mesh, extent of labeling: 1.0-1.5 mmol/g loading, 1 % cross-linked
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

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