BENZYL ALCOHOL

EC no.: 202-859-9; CAS no.: 100-51-6; Mol. formula: C7H8O; Benzyl Alcohol; Benzenemethanol; α-Hydroxytoluene; α-Toluenol; (Hydroxymethyl)benzene; Benzenecarbinol; Phenylcarbinol; Phenylmethanol; Phenylmethyl alcohol; Methanol, phenyl-; NCI-C06111; Hydroxytoluene; Bentalol; Benzoyl alcohol; Benzenmethanol; Benzylic alcohol; Methanol benzene; NSC 8044; Benzyl Alkohol
Preservative, antioxidant, and solvent for chemical industry.
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 is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Molecular formula: C7H8O
Molar mass: 108.138
CAS Registry Number: 100-51-6
Appearance: Benzyl alcohol, ACS, 99+%; Benzyl alcohol, 99%; Benzyl alcohol, ACS, 99+%; Benzyl alcohol, 99%; colourless liquid with a slightly pungent, faint aromatic, fruity odour; colourless liquid
Melting point: -15 °C
Boiling point: 205 to 206 °C
Solubility: Water, 4.29e+004 mg/L (25 deg C)
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 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.

Roles Classification 
Chemical Role(s):
Solvent (A liquid that can dissolve other substances (solutes) without any change in their chemical composition)
Antioxidant (A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides)
Biological Role(s):
Metabolite (Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites)
Application(s):Solvent (A liquid that can dissolve other substances (solutes) without any change in their chemical composition)
Fragrance (A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell)

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 it can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.

It 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.

It is also used in e-liquid for e-cigarettes to enhance the flavors used. When applied to damaged skin or mucous membranes at a 10% concentration, it acts as a local anesthetic and antimicrobial agent. It can be utilized as a degreaser in rug cleaning products. As a dye solvent, it enhances the process of dying wool, nylon, and leather.It also has use as a photographic film developer and as an insect repellent

It is often added to intravenous medication solutions as a preservative due to its bacteriostatic and antipruritic properties. It is also used as a photographic developer. Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications. It is oxidized rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. High concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis. Newborns, especially if critically ill, may not metabolize benzyl alcohol as readily as adults. Reports in the early 1980s of sixteen neonatal deaths associated with the use of saline flush solutions containing benzyl alcohol preservative led to recommendations to avoid its use in neonates.

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.

Other uses
Benzyl alcohol has nearly the same refraction index as quartz and wool fiber. If a clear quartz object is immersed in benzyl alcohol, it becomes almost invisible. This test has been used to determine non-destructively whether an object is truly made of quartz.Similarly, white wool immersed in benzyl alcohol also becomes almost invisible, clearly revealing contaminants such as dark and medullated fibers and vegetable matter.

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. It 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. It 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

Benzyl alcohol appears as 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 an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent. It has a role as a solvent, a metabolite, an antioxidant and a fragrance.

Properties
Chemical
Benzyl alcohol can be oxidized to benzaldehyde and benzoic acid.
Reaction with concentrated hydrochloric acid will yield benzyl chloride.

Physical
Benzyl alcohol is a colorless liquid, almost odorless, slightly soluble in water.

Availability
Benzyl alcohol is sold by chemical suppliers. Can also be purchased online.
Benzyl alcohol can sometimes be found in hardware and art/painting stores as solvent, mostly pure, though most of the time mixed with other solvents.
Some window cleaning products and mouthwashers contain benzyl alcohol, albeit in a small percentage.

Preparation
Can be prepared by hydrolyzing benzyl chloride with sodium hydroxide.
The benzyl chloride used for the reaction can be obtained by chlorinating toluene under UV light.

BENZYL ALCOHOL IN COSMETICS:
TYPE OF INGREDIENT:Preservative, antioxidant, and solvent
MAIN BENEFITS:Preserves, stabilizes, and dissolves ingredients
WHO SHOULD USE IT:In general, benzyl alcohol is safe to use by anyone who does not have a true contact allergy to it. Krant adds that those who prefer un-preserved products would want to avoid products containing standard preservatives like benzyl alcohol, though it may risk contamination.
HOW OFTEN CAN YOU USE IT:Benzyl alcohol is safe to use on a daily basis if you're not sensitive to it and if it's used at a low concentration.
WORKS WELL WITH:Benzyl alcohol works well with most, if not all, other ingredients.
DON'T USE WITH:Benzyl alcohol works well with most, if not all, other ingredients.

What Is Benzyl Alcohol?
Although it's most widely known as benzyl alcohol, the aromatic alcohol also goes by a few other names, such as benzenemethanol or phenylcarbinol. It's 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. 
"It's 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 for Skin
Besides 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 is also shown to function as a solvent and helps to dissolve other ingredients in a product's formula.
Decreases viscosity: Studies show benzyl alcohol also improves 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.

Side Effects of Benzyl Alcohol
"Benzyl alcohol is considered to be a safe ingredient in skincare and cosmetics when used on intact skin," Krant says. With that said, you might have seen benzyl alcohol on a list of "bad" alcohols once or twice before.

Can cause itching for some people: "As is the case for most preservatives, benzyl alcohol can, unfortunately, be an irritant and cause itching for some people," says Krant.
Toxicity is possible with overuse: "Toxicity is a possibility with excessive ingestion, which is not considered a risk with normal usage," says Wong, adding that it's safe when used at a low concentration—and it usually is in well-formulated products.
However, Krant points out that only in rare cases is someone actually allergic to benzyl alcohol. If you experience an adverse reaction (such as swelling, or redness) to products containing benzyl alcohol and suspect you could have an allergy to it, Krant says this can be identified through formal skin allergy patch testing with your dermatologist or allergist.

As for more serious risks of using the preservative in your products, those concerns aren't as valid. "The potential for allergenicity is low, and low risk of toxicity," Krant says.

How to Use It
As long as you don't have an allergy to benzyl alcohol, Krant and Wong say it's totally fine to use in your regular skincare routine. Because the ingredient is included in such a wide range of cosmetics, the time of day you would apply it, as well as the step in your routine, depends on each specific product.

alcohol bencílico (es)
alcool benzilico (it)
alcool benzylique (fr)
alkohol benzylowy (pl)
Bensüülalkohol (et)
Bentsyyli-alkoholi (fi)
benzil alcool (ro)
benzil alkol (tr)
benzil alkol ( türkçe)
benzilalkol( türkçe)
benzil alkohol (sl)
benzil-alkohol (hr)
benzilo alkoholis (lt)
benzilspirts (lv)
benzylalcohol (nl)
benzylalkohol (cs)
fenylokarbinol (pl)
fenylometanol (pl)
álcool benzílico (pt)
βενζυλική αλκοόλ (el)
бензилов алкохол (bg)
CAS names: Benzenemethanol

IUPAC names: Alcool, benzylique; Benzenemethanol, Phenylcarbinol;Benzyl alcohol, Phenylmethanol; benzyl alcohol; benzenemethanol; phenylmethanol; benzyl alkohol; Benzylic alcohol; Bezyl alcohol; fenilmetanol; fenylmethanol;hydroxymethylobenzene
;Phenyl methanol; phenyl-methanol; Phenylcarbinol; PHENYLMETHANOL; Phenylmethyl alcohol; Phenylmethylalcohol

Trade names
(Hydroxymethyl)benzene
.alpha.-Hydroxytoluene
.alpha.-Toluenol
ALPHA-HYDROXYTOLUOL
ALPHA-OXYTOLUOL
Benzenecarbinol
Benzenemethanol (9CI)
BENZOLCARBINOL
BENZOLMETHANOL
Benzyl alcohol (8CI)
HYDROXYMETHYLBENZOL
PHENYLMETHYLALKOHOL
Sunmorl BK 20
Üveglakk 1:1 B komponens
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
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]
HOCH-Ph-polymer
phenylmethan-1-ol
BnOH
Benzyl alcohol Natural
Benzyl alcohol [USAN:INN:JAN]
EINECS 202-859-9
EPA Pesticide Chemical Code 009502
BRN 0878307
TOLUENE,ALPHA-HYDROXY
66072-40-0
Phenyl Methanol
Benzyl alcohol, ACS reagent
Benzyl alcohol, for analysis
MBN
Ulesfia
Alcool benzilico
Alcohol bencilico
CAS-100-51-6
Ulesfia (TN)
Benzyl alcohol, 98+%, Extra Dry, AcroSeal(R)
Benzylalcohol
Benzalalcohol
Benzalcohol
Bentanol
Benzyl alcohol, specified according to requirements of Ph.Eur.
Alcoolbenzylique
benzene-methanol
Benzyl Alcohole
a-Hydroxytoluene
a-Toluenol
Benzenemethanol.
Benzyl alcohol [INN:JAN:NF]
Sunmorl BK 20
Nat. Benzyl Alcohol
PhCH2OH
Bn-OH
C6H5CH2OH
EC 202-859-9
PINAPUR™ 9 BA-R
Benzyl alcohol (JP15/NF)
Benzyl alcohol, 99%, pure
$l^{1}-oxidanylmethylbenzene
4-06-00-02222 (Beilstein Handbook Reference)
Benzyl alcohol, LR, >=99%
Benzyl alcohol (Benzenemethanol)
Benzyl alcohol (JP17/NF/INN)
Benzyl Alcohol Reagent ACS Grade
Pharmakon1600-01502555
Benzyl alcohol, analytical standard
Benzyl alcohol, AR, >=99.5%
Benzyl alcohol, anhydrous, 99.8%
Benzyl alcohol, >=99%, FCC, FG
Benzyl alcohol, natural, >=98%, FG
Benzyl alcohol, ACS reagent, >=99.0%
Benzyl alcohol, ReagentPlus(R), >=99%
Benzyl alcohol, USP, 98.0-100.5%
Benzyl alcohol, tested according to Ph.Eur.
E1519
Benzyl alcohol, p.a., ACS reagent, 99.0%
Benzyl alcohol, Vetec(TM) reagent grade, 98%
benzyl alcohol;BENZYL ALCOHOL;Benzenemethanol
Benzyl alcohol, certified reference material, TraceCERT(R)
Benzyl alcohol on polystyrene, 3.5 mmol/g@CRLFMFCD03792087
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)benzene
100-51-6 [RN]
202-859-9 [EINECS]
878307 [Beilstein]
Alcohol bencílico [Spanish] 
Alcohol benzylicus
alcoholum benzylicum [Latin] 
Alcool benzilico [Italian]
Álcool benzílico [Russian]
Alcool benzylique [French] 
Alkohol benzylowy [Polish]
Benzenemethanol [ACD/Index Name]
benzyl alcohol; benzylalcohol; Benzylalkohol [German]; BnOH; Phenylmethanol [ACD/IUPAC Name] 
Phenylmethanol [German] 
Phénylméthanol [French] 
phenylmethyl alcohol
Ulesfia [Trade name]
Βενζυλική αλκοόλη [Modern Greek (1453-)]
бензиловый спирт [Russian] 
ベンジルアルコール [Japanese]
كحول بنزيل [Arabic] 
苯甲醇 [Chinese] 
&α;-hydroxytoluene
1336-27-2 [RN]
14915-25-4 [RN]
185532-71-2 [RN]
4-06-00-02222 (Beilstein Handbook Reference) [Beilstein]
66072-40-0 [RN]
68661-10-9 [RN]
71258-23-6 [RN]
a-Hydroxytoluene
alcohol bencílico
alcoholum benzylicum
alcool benzylique
Alcoolbenzylique
Aromatic alcohol
a-Toluenol
Bentalol
Benzal alcohol
Benzalalcohol
Benzalcohol
Benzencarbinol
benzenecarbinol
Benzenmethanol
Benzoyl alcohol
Benzyl alcohol|Phenylmethanol
Benzyl Alcohole
Benzyl alkohol
Benzylalcohol 100 µg/mL in Methanol
Benzylalkohol
benzylic alcohol
Benzylicum
HYDROXYMETHYLBENZENE
hydroxytoluene
Methanol benzene
Methanol, phenyl-
MFCD03792087 [MDL number]
Nat. Benzyl Alcohol
O-Benzylhydroxylamine
OBZ
Phenolcarbinol
Phenyl carbinol
Phenylcarbinol [Wiki]
Phenylcarbinolum
phenylmethan-1-ol
Phenyl-methanol
Phenylmethanol, Benzenemethanol
Q1R [WLN]
Toluene [ACD/IUPAC Name] [Wiki]
WLN: Q1R
α-Hydroxytoluene
α-Hydroxytoluene
α-toluenol
α-Toluenol
бензиловый спирт
كحول بنزيل
苯甲醇