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Benzyl alcohol(CAS No. 100-51-6)

Benzyl alcohol C7H8O (cas 100-51-6) Molecular Structure

100-51-6 Structure

Identification and Related Records

Benzyl alcohol
【CAS Registry number】
Benzyl alcohol 98+%
Benzyl Alcohol BP
Benzoyl alcohol
Phenylmethyl alcohol
【Molecular Formula】
C7H8O (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

colourless liquid
【Melting Point】
【Boiling Point】
0.158mmHg at 25°C
【Refractive Index】
【Flash Point】
4.29 g/100 mL (20℃)
4.29 g/100 mL (20°C) in water
Water-white liquid
【Storage temp】
【Spectral properties】
SADTLER REF NUMBER: 157 (IR, PRISM); 985 (IR, GRATING); MAX ABSORPTION (ALCOHOL): 243 NM (LOG E= 1.91); 258.5 NM (LOG E= 2.26); 268 NM (LOG E= 1.95)
Index of refraction: 1.5396 at 20 deg C/D
IR: 5219 (Coblentz Society Spectral Collection)
UV: 62 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 161 (Varian Associates NMR Spectra Catalogue)
MASS: 61913 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 204 (National Bureau of Standards)
【Computed Properties】
Molecular Weight:108.13782 [g/mol]
Molecular Formula:C7H8O
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:1
Exact Mass:108.057515
MonoIsotopic Mass:108.057515
Topological Polar Surface Area:20.2
Heavy Atom Count:8
Formal Charge:0
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
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】
Hazard Codes:Xn,T
Risk Statements:20/22-63-43-36/37/38-23/24/25-45-40
20/22:Harmful by inhalation and if swallowed
63:Possible risk of harm to the unborn child
43:May cause sensitization by skin contact
36/37/38:Irritating to eyes, respiratory system and skin
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
45:May cause cancer
40:Limited evidence of a carcinogenic effect
Safety Statements:26-36/37-24/25-23-53
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37:Wear suitable protective clothing and gloves
24/25:Avoid contact with skin and eyes
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
53:Avoid exposure - obtain special instruction before use
RIDADR:UN 1593 6.1/PG 3
WGK Germany:1
Hazardous Substances Data:100-51-6(Hazardous Substances Data)
【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
It is slightly irritating to the skin.
Vapor: Irritating to eyes, nose and throat. Liquid: Irritating to skin & eyes.
【Cleanup Methods】
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner. /Benzyl alcohol (Combustible liquid, NOS)/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Benzyl alcohol (Combustible liquid, NOS)/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Benzyl alcohol (Combustible liquid, NOS)/
UN 1593 6.1/PG 3
【Fire Fighting Procedures】
Foam, carbon dioxide, dry chem.
Alcohol foam. Water or foam may cause frothing.
If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Benzyl alcohol (Combustible liquid, NOS)/
【Fire Potential】
Slight, when exposed to heat or flame.
The LIQ is flammable & a moderate fire hazard.
Grades: free from chlorine (FFC); technical; NF (National Formulary); textile; photographic reagent; FCC
Euxyl K 100
Pure, photo, pharmaceutical, and perfume grades, 99% min purity, liquid form
Bacteriostatic Water for Injection, USP is a sterile, nonpyrogenic preparation of water for injection containing 0.9% (9 mg/mL) of benzyl alcohol added as a bacteriostatic preservative. /Bacteriostatic Water for Injection/
【Exposure Standards and Regulations】
Local anesthetic active ingredients. The active ingredient of the product consists of any of the following when used in the concentration or within the concentration range established for each ingredient: Benzyl alcohol 1 to 4 percent is included on this list.
【Reactivities and Incompatibilities】
A mixture of benzyl alcohol with 58% sulfuric acid decomp expliosively at about 180 deg C.
Incompatible with oxidizing agents.
Possible problems may occur when polystyrene syringes are used with certain types of drug products that contain paraaldehyde, benzaldehyde & benzyl alcohol since these agents can extract & dissolve the plastic. At times the rubber tip of the plunger may release a constituent to the drug product.
Benzyl alcohol containing acidic constituents and dissolved iron was found to polymerize with a rapid temperature increase when heated in excess of 100 deg C. Amines, pyridene, and alkali hydroxides act as inhibitors and prevent polymerization.
【Other Preventative Measures】
Ventilation control: The basic ventilation methods are local exhaust ventilation & dilution or general ventilation.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
Substitution of less irritating substances.Redesign of operations. Prevent contact, provision of a physical barrier against contact, proper washing facilities, work clothing & storage facilities, protective clothing, & barrier creams. medical control.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Benzyl alcohol (Combustible liquid, NOS)/
Personnel protection: Keep upwind. Avoid breathing vapors. Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material. /Benzyl alcohol (Combustible liquid, NOS)/
【Protective Equipment and Clothing】
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles. /Benzyl alcohol (Combustible liquid, NOS)/
【Octanol/Water Partition Coefficient】
log Kow = 1.10
【Disposal Methods】

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing
(a) By hydrolysis of benzyl chloride; (b) from benzaldehyde by catalytic reduction or Cannizzaro reaction.
Benzyl alcohol can be produced by 1) the hydrolysis of benzyl chloride and 2) the hydrogenation of benzaldehyde.
The hydrogenation of methyl benzoate in the presence of a copper-chromium catalyst is a feature of a three-step process for the production of benzyl alcohol from toluene. The first step is the oxidation of toluene to form benzoic acid. The acid is esterified with methanol in the second step. The hydrogenation of methyl benzoate to form benzyl alcohol is performed in the final step.
Other processes for the production of benzyl alcohol include the hydrogenation of benzoic acid, the electrochemical reduction of benzoic acid, the hydrolysis of benzylsulfonic acid, and the decarboxylation of benzyl formate. These processes have no importance in the industrial production of benzyl alcohol, but they may be used to produce derivatives substituted on the aromatic nucleus.
Benzyl alcohol is manufactured on a commercial scale from benzyl chloride and sodium carbonate.
Originally prepd by Cannizzaro reaction from benzaldehyde and potassium hydroxide. Produced on large scale by action of potassium carbonate on benzyl chloride: German patent 484,662; Chem Zentr 1930, I, 1052; FRDL 16, 426
Synthesis: By saponification of the ester present in Tolu and Pery balsams; synthetically, it is obtained from benzyl chloride by the action of sodium or potassium carbonate.

U.S. Imports
(1975) 3.53X10+6 (PRINCPL CUSTMS DISTS)
(1983) 8.25X10+8 g

U.S. Production
(1971) 4.22X10+9 G
(1975) 5.84X10+9 G
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >10 million - 50 million 1990 >1 million - 10 million 1994 >10 million - 50 million 1998 >10 million - 50 million 2002 >10 million - 50 million
Benzyl alcohol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Consumption Patterns
60% is used in the textile industry as a dye assistant (mostly for dyeing nylon carpeting); and 40% is used in other applications (1972)

Biomedical Effects and Toxicity

【Pharmacological Action】
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
【Therapeutic Uses】
On April 9, 2009, the U.S. Food and Drug Administration approved a new prescription medication for the treatment of head lice ( Pediculosis capitis ) infestation. Benzyl Alcohol Lotion, 5%, received full market approval as a prescription medication, for use in patients 6 months of age and older. Benzyl Alcohol Lotion, 5%, is the first head lice product approved by the FDA with benzyl alcohol as the active pharmaceutical ingredient.
The safety and effectiveness of Benzyl Alcohol Lotion, 5%, was demonstrated in two studies of 628 people, 6 months of age and older, with active head lice infestation. The subjects received two, 10-minute treatments of either Benzyl Alcohol Lotion or a topical placebo, one week apart. Fourteen days after the final treatment, more than 75 percent of the subjects treated with Benzyl Alcohol Lotion, 5%, were lice free.
In each of two double-blind studies, 25 patients suffering from early progressive idiopathic cataracts, subcapsular or cortical in site, received one drop of saline containing 0.07% benzyl alcohol every 8 hours. The eyelid was held open for at least 2 minutes. Treatment continued for 22 months. In one study, a control group received placebo, whereas in the other study, the control group received an anticataract medication. Clinical findings were recorded every 30 days for the first 14 months, then patients were followed for up to 18 and 22 months. A significant (p < .01) increase in visual acuity (VA) was observed in patients treated with benzyl alcohol after 30 and 60 days as compared to those receiving either placebo or the medication. Compared to those placebo or medication treated, a significant (p < .01) decrease in lens opacity was noted in 19 and 17 patients treated with benzyl alcohol, respectively. In the course of the studies, a significant increase in the number of surgeries for cataracts was noted in patients not receiving benzyl alcohol. One patient treated with benzyl alcohol required surgery after 22 months compared to 38 total who had received either placebo or medication. benzyl alcohol was well tolerated except in two patients (4%) where tolerance was fair in one and poor in the other. [Benzyl Alcohol. Cosmetic Ingredient Review; International Journal of Toxicology; 20(suppl 3):23-50 (2001)]
【Biomedical Effects and Toxicity】
The percutaneous absorption was determined in vivo in rhesus monkeys. Absorption through occluded skin was high (56-80 %) in 24 hr. No correlation was seen between skin penetration and the octanol-water partition coefficient. Under unoccluded conditions skin penetration was reduced (32 %), because of evaporation of the compound.
High levels of benzyl alcohol (5-500 ug/10 mL plasma) were found in uremic patients on hemodialysis; benzyl alcohol was not detected in normal controls.
Rabbits given 1 g of benzyl alcohol sc eliminated 300-400 mg of hippuric acid within the following 24 hr. Within 6 hr after oral administration of 0.40 g benzyl alcohol/kg bw, rabbits eliminated 65.7% of dose as hippuric acid in the urine.
In humans and animals, benzyl alcohol was readily absorbed from the gastrointestinal tract. Percutaneous absorption was high following topical use. Rhesus monkeys absorbed 56-80% of a topical dose administered under occlusive conditions in 24 hours; absorption was less under unoccluded conditions due to evaporation. Benzyl alcohol rapidly disappeared from the injection site following intramuscular administration in rats; the disappearance half-life was estimated to be less than 10 minutes.
Vapors can penetrate the intact skin.
The dermal flux for benzyl alcohol across human skin in vitro was reported at 0.073 mg/sq cm/hr, indicating a low rate of dermal uptake. The percentage of the applied dose that penetrated through human skin in vitro in 6 hr was 1.42% for adult skin and 0.73% for full term infant skin.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme, Koc values of
AQUATIC FATE: Based on a classification scheme, Koc values of
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere, benzyl alcohol, which has a vapor pressure of 9.4X10-2 mm Hg at 25 deg C, is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzyl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 deg C. Benzyl alcohol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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