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100-51-6

Basic Information
CAS No.: 100-51-6
Name: Benzyl alcohol
Article Data: 2360
Molecular Structure:
Molecular Structure of 100-51-6 (Benzyl alcohol)
Formula: C7H8O
Molecular Weight: 108.14
Synonyms: Benzyl alcohol (JP14/NF);Phenylmethyl alcohol;alpha-Hydroxytoluene;phenylcarbinol;Benzenecarbinol;.alpha.-Hydroxytoluene;(Hydroxymethyl)benzene;Phenylmethanol;Benzal alcohol;benzenemethanol;.alpha.-Toluenol;Methanol, phenyl-;Sunmorl BK 20;NCI-C06111;see Carbamo(dithioperox)imidic acid,phenylmethyl ester;Benzyl alcohol F.F.C.;Benzyl Alcohol , Natural;Benzyl alcohol nat.;benzoic alcohol;Benzyl Alcohol, Reagent;Phenolcarbinol;Phenyl Methanol;FEMA No. 2137;alpha-Toluenol;Benzyl Alcohol Natural;BenzylAlcohol(PhenylCarbinol);
EINECS: 202-859-9
Density: 1.047 g/cm3
Melting Point: -15 °C
Boiling Point: 204.7 °C at 760 mmHg
Flash Point: 97.5 °C
Solubility: 4.29 g/100 mL (20°C) in water
Appearance: colourless liquid
Hazard Symbols: HarmfulXn,ToxicT
Risk Codes: 20/22-63-43-36/37/38-23/24/25-45-40
Safety: 26-36/37-24/25-23-53
Transport Information: UN 1593 6.1/PG 3
PSA: 20.23000
LogP: 1.17890
Synthetic route
93-89-0

benzoic acid ethyl ester

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.5h;100%
With RuCl2(2-(diphenylphosphino)-N-(thiophen-2-ylmethyl)ethanamine)PPh3; hydrogen; sodium methylate In toluene at 100℃; under 37503.8 Torr; for 16h; Autoclave;100%
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 4.5h;99%
100-52-7

benzaldehyde

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With Triethoxysilane; potassium fluoride for 36h; Product distribution;100%
With n-butyllithium; 1-methoxycyclohexa-1,4-diene In tetrahydrofuran; Petroleum ether for 5h; Product distribution; Ambient temperature;100%
With sodium tetrahydroborate In methanol; dichloromethane at 22℃; for 0.00166667h; also in other alcohols, also at other temperatures, also the reduction time required for 50percent reduction;100%
98-88-4

benzoyl chloride

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; silica gel In hexane at 25℃; for 3h;100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;100%
With trihexyl(tetradecyl)phosphonium decanoate*BH3 at 20℃; Product distribution / selectivity;99%
93-58-3

benzoic acid methyl ester

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C32H34BrN5ORu; potassium tert-butylate; hydrogen In tetrahydrofuran at 70℃; under 37503.8 Torr; for 4h; Reagent/catalyst;100%
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C32H32Cl2N2P2Ru; hydrogen; sodium methylate In para-xylene; toluene at 5 - 100℃; under 37503.8 Torr; for 4h; Reagent/catalyst; Glovebox;100%
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; deprotection;100%
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 30h; Hydrolysis;99%
With C24H20O3; toluene-4-sulfonic acid In tetrahydrofuran; methanol at 20℃; for 1h;99%
14642-79-6

benzyloxy-trimethylsilane

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; deprotection;100%
With water; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 20℃; for 0.25h;100%
montmorillonite K-10 for 0.0166667h; Solid phase reaction; desilylation; microwave irradiation;99%
22768-01-0

O-Alloc benzyl alcohol

A

187737-37-7

propene

B

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene at 5℃;A n/a
B 100%
104-57-4

benzyl formate

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In o-xylene at 80℃; for 24h; Inert atmosphere;100%
Stage #1: benzyl formate With phenylsilane; C74H74Mn2N6P4 at 25℃; for 0.5h; Glovebox; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 25℃; for 2h; Glovebox; Inert atmosphere;
99%
Stage #1: benzyl formate With phenylsilane; (Ph2PPrPDI)Mn at 25℃; for 0.25h; Glovebox; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 25℃; for 2h; Catalytic behavior; Reagent/catalyst; Glovebox;
88%
120-51-4

benzoic acid benzyl ester

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2h;99%
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;99%
99464-81-0

benzyl (1-chloroethyl) carbonate

ammonium thiocyanate

A

117972-00-6

benzyl 1-thiocyanoethylcarbonate

B

100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tetrabutyl phosphonium bromide In acetone for 18.5h; Heating;A 100%
B 18%
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Specification

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. With the cas number 100-51-6, it is also called (Hydroxymethyl)benzene;alcoolbenzylique;Bentalol;benzalalcohol;Benzalcohol;Benzenemethan-lo;benzenmethanol;Benzoyl alcohol. Benzyl Alcohol is an aromatic alcohol used as a preservative, as the active ingredient in head lice treatment, and as a solvent. It is most often created by combining benzyl chloride (a suspected carcinogen that has been used as a war gas) with sodium hydroxide (lye).

Physical properties about Benzyl alcohol are: (1)ACD/LogP: 1.055; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.06; (4)ACD/LogD (pH 7.4): 1.06; (5)ACD/BCF (pH 5.5): 3.73 ; (6)ACD/BCF (pH 7.4): 3.73; (7)ACD/KOC (pH 5.5): 89.37 ; (8)ACD/KOC (pH 7.4): 89.37; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.546; (13)Molar Refractivity: 32.704 cm3; (14)Molar Volume: 103.25 cm3; (15)Polarizability: 12.965 10-24cm3; (16)Surface Tension: 40.7179985046387 dyne/cm; (17)Density: 1.047 g/cm3; (18)Flash Point: 97.507 °C ; (19)Enthalpy of Vaporization: 46.614 kJ/mol; (20)Boiling Point: 204.699 °C at 760 mmHg; (21)Vapour Pressure: 0.158000007271767 mmHg at 25°C

Preparation of Benzyl Alcohol: 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. Benzyl alcohol is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:
C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl
It can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C6H5MgBr) with formaldehyde, followed by acidification.

Uses of Benzyl Alcohol: Benzyl Alcohol (CAS NO.100-51-6) is used as a bacteriostatic preservative at low concentration in intravenous medications. It is also used as a general solvent for inks, paints, lacquers, and epoxy resin coatings.In organic synthesis, benzyl esters are good protecting groups due to they can be removed by mild hydrogenolysis. Besides Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires. Moreover it is also a precursor to a variety of esters, used in the soap, perfume, and flavor industries. It is often added to intravenous medication solutions as a preservative because of its bacteriostatic and antipruritic properties. At last it is also used as a photographic developer.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing and gloves;
3. Avoid contact with skin and eyes;
4. Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer);
5. Avoid exposure - obtain special instruction before use;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2;
(2)InChIKey=WVDDGKGOMKODPV-UHFFFAOYSA-N;
(3)Smilesc1(ccccc1)CO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
 
cat LDLo intravenous 625mg/kg (625mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 16, Pg. 1, 1920.
cat LDLo skin 10gm/kg (10000mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: TREMOR
Journal of Pharmacology and Experimental Therapeutics. Vol. 84, Pg. 358, 1945.
dog LDLo intravenous 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Toxicology and Applied Pharmacology. Vol. 18, Pg. 60, 1971.
 
dog LDLo parenteral 9mg/kg (9mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 25, Pg. 153, 1973.
 
guinea pig LD50 oral 2500mg/kg (2500mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(7), Pg. 81, 1985.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmaceutical Sciences. Vol. 75, Pg. 702, 1986.
 
mouse LD50 intravenous 324mg/kg (324mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 330, 1962.
 
mouse LD50 oral 1360mg/kg (1360mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(7), Pg. 81, 1985.
rabbit LD50 oral 1040mg/kg (1040mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 84, Pg. 358, 1945.
rabbit LD50 skin 2gm/kg (2000mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 6, 1974.
rat LCLo inhalation 1000ppm/8H (1000ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD50 intraarterial 441mg/kg (441mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA
Toxicology and Applied Pharmacology. Vol. 18, Pg. 60, 1971.
 
rat LD50 intraperitoneal 400mg/kg (400mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 6, 1974.
rat LD50 intravenous 53mg/kg (53mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Toxicology and Applied Pharmacology. Vol. 18, Pg. 60, 1971.
 
rat LD50 oral 1230mg/kg (1230mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LDLo subcutaneous 1700mg/kg (1700mg/kg) BEHAVIORAL: COMA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES 

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.

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