BENZYL ALCOHOL (PHENYL CARBINOL)

Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) is denoted as BnOH. 
Benzyl alcohol (phenyl carbinol) is a colorless liquid with a mild pleasant aromatic odor. 

CAS:    100-51-6
MF:    C7H8O
MW:    108.14
EINECS:    202-859-9

Synonyms    Benzylalkohol;benzylalcohol,benzylalcohol,benzenemethanol;PHENYLMETHANOL/BENZYLALCOHOL;BENZYL ALCOHOL (TECH);BENZYL ALCOHOL NF FCC KOSHER;BENZYL ALCOHOL PERFUME GRADE 99.5% FCC NF;BENZYLALCOHOL,NF;BENZYLALCOHOL,REAGENT,ACS(BULK;benzyl alcohol;phenylmethanol;benzenemethanol;100-51-6;phenylcarbinol;benzylalcohol;Benzoyl alcohol;Benzenecarbinol;alpha-Toluenol;Phenylmethyl alcohol;Hydroxytoluene;(Hydroxymethyl)benzene;Phenolcarbinol;Benzal alcohol;Methanol, phenyl-;alpha-hydroxytoluene;benzylic alcohol;Alcool benzylique;Benzylicum;Phenylcarbinolum;Euxyl K 100;hydroxymethylbenzene;Bentalol;Ulesfia;66072-40-0;Phenyl Methanol;Phenyl-Methanol;BENZYL-ALCOHOL;Caswell No. 081F;alcoholum benzylicum;Benzyl alcohol (natural);FEMA No. 2137;Benzylalkohol;NCI-C06111;Alcool benzilico;Aromatic alcohol;Alcohol, Benzyl;Alcohol bencilico;.alpha.-Toluenol;Alcool benzilico [DCIT];Itch-X;NSC 8044;HSDB 46;benzenmethanol;.alpha.-Hydroxytoluene;Benzalalcohol;Benzalcohol;CCRIS 2081;Aromatic primary alcohol;Alcoolbenzylique;Alcohol,benzyl;Alcool benzylique [INN-French];Benzyl alkohol;Alcohol bencilico [INN-Spanish];Methanol benzene;Alcoholum benzylicum [INN-Latin];UNII-LKG8494WBH;Alcohol benzylicus;NSC-8044;EINECS 202-859-9;BnOH;LKG8494WBH;MFCD00004599;EPA Pesticide Chemical Code 009502;BRN 0878307;Sunmorl BK 20;DTXSID5020152;CHEBI:17987;INS NO.1519;AI3-01680;INS-1519;Hydroxymethyl resin (100-200 mesh);TOLUENE,ALPHA-HYDROXY;DTXCID70152;Benzyl alcohol (Benzenemethanol);E-1519;EC 202-859-9
;4-06-00-02222 (Beilstein Handbook Reference);185532-71-2;NCGC00091865-01;BENZYL ALCOHOL (II);BENZYL ALCOHOL [II];MBN;BENZYL ALCOHOL (MART.);BENZYL ALCOHOL [MART.];Alcool benzylique (INN-French);BENZYL ALCOHOL (USP-RS);BENZYL ALCOHOL [USP-RS];benzyl alcohol (ring-13c6);Alcohol bencilico (INN-Spanish);Alcoholum benzylicum (INN-Latin);BENZYL ALCOHOL (EP MONOGRAPH);BENZYL ALCOHOL [EP MONOGRAPH];phenylmethan-1-ol;CAS-100-51-6;Ulesfia (TN);Benzyl alcohol [USAN:INN:JAN];enzylalcohol;Protocoxil;phenyl carbinol;benzene-methanol;Benzyl Alcohole;a-Hydroxytoluene;a-Toluenol;Alcohol benzilico;Benzyl alcohol [INN:JAN:NF];Hydroxymethyl resin (200-400 mesh);PhCH2OH;Bn-OH;SCHEMBL147;Benzyl alcohol, ACS grade;bmse000407;C6H5CH2OH;CHEMBL720;WLN: Q1R;BENZYL ALCOHOL [MI];Benzyl alcohol (JP15/NF);BENZYL ALCOHOL [FCC];BENZYL ALCOHOL [INN];BENZYL ALCOHOL [JAN];BENZYL ALCOHOL [FHFI];BENZYL ALCOHOL [HSDB];BIDD:ER0248;ALCOHOL,BENZYL [VANDF];BENZYL ALCOHOL [VANDF];ZilactinEarly Relief Cold Sore;TB 13G;Benzyl alcohol, LR, >=99%;BENZYL ALCOHOL [WHO-DD];BENZYL ALCOHOL [WHO-IP];BDBM16418;NSC8044;Benzyl alcohol (JP18/NF/INN);HMS3264B16;HMS3885F10;Pharmakon1600-01502555;Benzyl alcohol, analytical standard;Benzyl alcohol, AR, >=99.5%;HY-B0892;Benzyl alcohol, anhydrous, 99.8%

Benzyl alcohol (phenyl carbinol) is useful as a solvent for its polarity, low toxicity, and low vapor pressure. 
Benzyl alcohol (phenyl carbinol) 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.
Benzyl alcohol (phenyl carbinol) is also known as Benzyl alcohol (phenyl carbinol). 
Benzyl alcohol (phenyl carbinol)'s chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit). 
Benzyl alcohol (phenyl carbinol) is one of the simplest fatty alcohol containing phenyl. 
Benzyl alcohol (phenyl carbinol) can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl. 
Benzyl alcohol (phenyl carbinol) is a colorless transparent sticky liquid with faint aroma. 
Sometimes Benzyl alcohol (phenyl carbinol) is placed for a long time, it will smells like bitter almond flavor because of oxidation. Polarity, low toxicity and low steam, so it is used as alcohol solvent. 
Benzyl alcohol (phenyl carbinol) is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol). 

Benzyl alcohol (phenyl carbinol) is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.
Benzyl alcohol (phenyl carbinol) mainly exists in the form of free or ester in essential oil, such as jasmine oil, ylang-ylang oil, jasmine oil, hyacinth oil, sesame oil, hyacinths balsam, peru balsam and tolu balsam, which all contain this ingredient.
Benzyl alcohol (phenyl carbinol) should not be stored for a long time. 
Benzyl alcohol (phenyl carbinol) can be slowly oxidized to benzaldehyde and anisole in the air.
Therefore Benzyl alcohol (phenyl carbinol) products often smell like almond aroma with characteristic of benzaldehyde. 
In addition, Benzyl alcohol (phenyl carbinol) is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.
Benzyl alcohol (phenyl carbinol) is a component catalyst for epoxy resins. 
Benzyl alcohol (phenyl carbinol) is also contained in the color developer C-22.
Benzyl alcohol (phenyl carbinol) is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent. 

Benzyl alcohol (phenyl carbinol) has a role as a solvent, a metabolite, an antioxidant and a fragrance.
An aromatic primary alcohol. 
Benzyl alcohol (phenyl carbinol) is synthesized by Cannizzaro’s reaction, which involves the simultaneous oxidation and reduction of benzenecarbaldehyde (benzaldehyde) by refluxing in an aqueous solution of sodium hydroxide:
2C6H5CHO → C6H5CH2OH + C6H5COOH
Benzyl alcohol (phenyl carbinol) undergoes the reactions characteristic of alcohols, especially those in which the formation of a stable carbonium ion as an intermediate (C6H5CH2 +) enhances the reaction. 
Substitution onto the benzene ring is also possible; the –CH2OH group directs into the 2- or 4-position by the donation of electrons to the ring.

Benzyl alcohol (phenyl carbinol) has been used as an antimicrobial agent in pharmaceutical preparations for many years. 
Parenteral administration of preparations containing 0.9% Benzyl alcohol (phenyl carbinol) resulted in the death of 16 neonates in the USA in the early 1980s. 
Many countries subsequently warned against using such preparations in neonates. 
This decision is not applicable to the use of Benzyl alcohol (phenyl carbinol) as a preservative in other circumstances or to its use in topical preparations and no country has placed a total ban on the compound.

A clear colorless liquid with a pleasant odor. 
Slightly denser than water. 
Flash point 194°F. 
Boiling point 401°F. 
Contact may irritate skin, eyes, and mucous membranes. 
May be slightly toxic by ingestion. 
Used to make other chemicals.
Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. 
Benzyl alcohol (phenyl carbinol) is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang.
Benzyl alcohol (phenyl carbinol) is also found in castoreum from the castor sacs of beavers.
Benzyl alcohol (phenyl carbinol) also occur naturally.

Benzyl alcohol (phenyl carbinol) Chemical Properties
Melting point: -15 °C
Boiling point: 205 °C
Density: 1.045 g/mL at 25 °C(lit.)
Vapor density: 3.7 (vs air)
Vapor pressure: 13.3 mm Hg ( 100 °C)
Refractive index: n20/D 1.539(lit.)
FEMA: 2137 | BENZYL ALCOHOL
Fp: 201 °F
Storage temp.: Store at +2°C to +25°C.
Solubility: H2O: 33 mg/mL, clear, colorless
Form: Liquid
pka: 14.36±0.10(Predicted)
Color: APHA: ≤20
Relative polarity: 0.608
Odor: Mild, pleasant.
Odor Type: floral
Explosive limit: 1.3-13%(V)
Water Solubility: 4.29 g/100 mL (20 ºC)
Merck: 14,1124
JECFA Number: 25
BRN: 878307
Henry's Law Constant: <2.70 x 10-7 at 25 °C (thermodynamic method-GC/UV, Altschuh et al., 1999)
Exposure limits: No exposure limit is set. Because of its low vapor pressure and low toxicity, the health hazard to humans from occupational exposure should be very low.
Dielectric constant: 13.1（20℃）
InChIKey: WVDDGKGOMKODPV-UHFFFAOYSA-N
LogP: 1.05 at 20℃
CAS DataBase Reference: 100-51-6(CAS DataBase Reference)
NIST Chemistry Reference: Benzyl alcohol (phenyl carbinol)(100-51-6)
EPA Substance Registry System: Benzyl alcohol (phenyl carbinol) (100-51-6)

Benzyl alcohol (phenyl carbinol) has a characteristic pleasant, fruity odor and a slightly pungent, sweet taste; the note tends to become similar to that of benzyl aldehyde on aging. 
Slightly soluble in water, and miscible with alcohol, ether, chloroform and so on.

Reactions
Like most alcohols, Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) reacts with acrylonitrile to give N-benzylacrylamide.
Benzyl alcohol (phenyl carbinol) is an example of a Ritter reaction:

C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2

Uses    
Benzyl alcohol (phenyl carbinol) is a colorless clear oily liquid; its odor type is floral and its odor at 100% is described as 'floral rose phenolic balsamic'.
Benzyl alcohol (phenyl carbinol) is used in cosmetics as afragrance component, preservative, solvent and diluting agent for perfumes and flavors, and viscosity-decreasing agent. 
Benzyl alcohol (phenyl carbinol) is used as a solvent for surface-coating materials, cellulose esters and ethers, alkyd resins,acrylic resins, fats, dyestuffs,casein (when hot), gelatin, shellac and waxes. 
Benzyl alcohol (phenyl carbinol) is added in small amounts to surface-coating materials to improve their flow and gloss. 
In the textile industry, Benzyl alcohol (phenyl carbinol) is used as anauxiliary in the dyeing of wool, polyamides, and polyesters. 
In pharmacy Benzyl alcohol (phenyl carbinol) is used as a local anesthetic ingredient in over-the-counter anorectal, oral healthcare and topical analgesic drug products and, because of its antimicrobial effect, as an ingredient of ointments and other preparations.
Benzyl alcohol (phenyl carbinol) is also a starting material for the preparation of numerous benzyl esters that are used as odorants, flavors, stabilizers for volatile perfumes, and plasticizers and is also employed in the extractive distillation of m- and p-xylenes and m- and p-cresols. 
Other uses include or have included heat-sealing of polyethylene films,in color photography as a development accelerator and in microscopy as embedding material.

Benzyl alcohol (phenyl carbinol) occurs in many essential oils and foods. 
Benzyl alcohol (phenyl carbinol)is a colorless liquid with a weak, slightly sweet odor. 
Benzyl alcohol (phenyl carbinol) can be oxidized to benzaldehyde, for example, with nitric acid. Dehydrogenation over a copper–magnesium oxide–pumice catalyst also leads to the aldehyde. 
Esterification of Benzyl alcohol (phenyl carbinol) results in a number of important fragrance and flavor materials. 
Diphenylmethane is prepared by a Friedel–Crafts reaction of Benzyl alcohol (phenyl carbinol) and benzene with aluminum chloride or concentrated sulfuric acid. 
By heating Benzyl alcohol (phenyl carbinol) in the presence of strong acids or strong bases, dibenzyl ether is formed.
Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor threshold concentration in water is 10 ppm.

Esters of Benzyl alcohol (phenyl carbinol) are used in makingperfume, soap, flavoring, lotion, and ointment.
Benzyl alcohol (phenyl carbinol) finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.
Benzyl alcohol (phenyl carbinol) occurs in natural products such as oils ofjasmine and castoreum.
Benzyl alcohol (phenyl carbinol) is widely used as a solvent for the dielectrophoretic reconfiguration of nanowires, inks, paints, lacquers and epoxy resin coatings and as a precursor to a variety of esters used in soaps, perfumes and flavoring. 
Benzyl alcohol (phenyl carbinol) is employed as a local anesthetic which reduces the pain associated with lidocaine injection. 
Benzyl alcohol (phenyl carbinol) has a various applications in baby products, bath products, soaps and detergents, eye makeup, blushers, cleansing products, make up products as well as hair, nail and skin care products.
Benzyl alcohol (phenyl carbinol) is a preservative against bacteria, used in concentrations of 1 to 3 percent. Benzyl alcohol (phenyl carbinol) can cause skin irritation.

Benzyl alcohol (phenyl carbinol) is used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings. 
Thus Benzyl alcohol (phenyl carbinol) can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.
Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) can be used as a local anesthetic, especially with epinephrine.
As a dye solvent, Benzyl alcohol (phenyl carbinol) enhances the process of dying wool, nylon, and leather.

Use in health care
Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) is used as benzaldehyde arises from benzyl alcohol when used as preservative in an injectable formulation solution.
Benzyl alcohol (phenyl carbinol), 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.
Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.
Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol) is a common ingredient in a variety of household products.

Pharmaceutical Applications    
Benzyl alcohol (phenyl carbinol) is an antimicrobial preservative used in cosmetics, foods, and a wide range of pharmaceutical formulations, including oral and parenteral preparations, at concentrations up to 2.0% v/v. 
The typical concentration used is 1% v/v, and Benzyl alcohol (phenyl carbinol) has been reported to be used in protein, peptide and small molecule products, although its frequency of use has fallen from 48 products in 1996, 30 products in 2001, to 15 products in 2006. 
In cosmetics, concentrations up to 3.0% v/v may be used as a preservative. 
Concentrations of 5% v/v or more are employed as a solubilizer, while a 10% v/v solution is used as a disinfectant.
Benzyl alcohol (phenyl carbinol) 10% v/v solutions also have some local anesthetic properties, which are exploited in some parenterals, cough products, ophthalmic solutions, ointments, and dermatological aerosol sprays.
Although widely used as an antimicrobial preservative, Benzyl alcohol (phenyl carbinol) has been associated with some fatal adverse reactions when administered to neonates. 
Benzyl alcohol (phenyl carbinol) is now recommended that parenteral products preserved with Benzyl alcohol (phenyl carbinol), or other antimicrobial preservatives, should not be used in newborn infants if at all possible.

Production Method    
1.Benzyl chloride with potassium or sodium is heated for a long timg, and hydrolyzes to yield benzyl alcohol.
2.Benzaldehyde in methanol and sodium hydroxide solution react to benzyl alcohol at 65~75 ℃. Benzyl alcohol (phenyl carbinol) has high purity.
3.Using benzyl chloride as raw materials, Benzyl alcohol (phenyl carbinol) is heated and hydrolyzes to yield benzyl alcohol in the presence of the sodium catalyst. 
Specification of spices benzyl alcohol(QB792-81): the relative density of 1.041-1.046; refractive index of 1.538-1.541; boiling range 203-206℃ and distillate volume more than 95%; dissolving completely in 30 volumes of distilled water; containing more than 98 percent of alcohol; chlorine test (NF) as the side reaction. 
Raw material consumption quota: benzyl chloride 1600kg/t; soda ash 1000kg/t.

4.Benzyl alcohol (phenyl carbinol) exists naturally in orange flower, ylang-ylang, jasmine, gardenia, acacia, lilac and hyacinth. 
Benzyl alcohol (phenyl carbinol) or benzaldehyde is used as raw materials to prepare benzyl alcohol in the industry.
5.Add chlorobenzyl to 12% sodium carbonate solution, heat to 93 ℃ and stir for 5h. 
Then warm the mixture to 101~103℃ and react for 10h. 
After the reaction, cool Benzyl alcohol (phenyl carbinol) to the room temperature, and add salt to saturation. 
After still standing for stratification, take the upper liquid and get crude products through pressure distillation. 
Then refine to gain the target products. 
The yield is 70%～72%.
C6H5CH2Cl+H2O[Na2CO3]→C6H5CH2OH+NaCl+CO2↑
In the presence of sodium hydroxide, formaldehyde and benzaldehyde react to produce benzyl alcohol by disproportionation reaction.
C6H5CHO+HCHO[NaOH]→C6h5CH2OH+HCOONa

Preparation
Benzyl alcohol (phenyl carbinol) 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 (phenyl carbinol). 
The latter also gives benzoic acid, an example of an organic disproportionation reaction.
Benzyl alcohol (phenyl carbinol) is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. 
Benzyl alcohol (phenyl carbinol) may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.

Reactivity Profile    
Acetyl bromide reacts violently with alcohols or water. 
Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. 
Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. 
Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. 
Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid. 

Alkyl hypochlorites are violently explosive. 
They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. 
Chlorine plus alcohols would similarly yield alkyl hypochlorites. 
They decompose in the cold and explode on exposure to sunlight or heat. 
Tertiary hypochlorites are less unstable than secondary or primary hypochlorites. 
Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. 
Such reactions in the absence of solvents often occur with explosive violence.

Health Hazard    
Benzyl alcohol (phenyl carbinol) is a low acute toxicant witha mild irritation effect on the skin. 
Theirritation in 24 hours from the pure compoundwas mild on rabbit skin and moderateon pig skin. 
A dose of 750 μg producedsevere eye irritation in rabbits. 
The toxicityof Benzyl alcohol (phenyl carbinol) is of low order,the effects varying with the species. Oralintake of high concentrations of this compoundproduced behavioral effects in rats.
The symptoms progressed from somnolenceand excitement to coma. 
Intravenous administrationin dogs produced ataxia, dyspnea,diarrhea, and hypermotility in the animals.
Adult and neonatal mice treated with Benzyl alcohol (phenyl carbinol)l exhibited behavioral change,including sedation, dyspnea, and loss ofmotor function. 
Pretreatment with pyrazoleincreased the toxicity of benzyl alcohol. 
With disulfiram the toxicity remained unchanged.
The study indicated that the acute toxicitywas due to the alcohol itself andnot to bezaldehyde, its primary metabolite.