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Basic Information
CAS No.: 140-11-4
Name: alpha-Acetoxytoluene
Article Data: 733
Molecular Structure:
Molecular Structure of 140-11-4 (alpha-Acetoxytoluene)
Formula: C9H10O2
Molecular Weight: 150.177
Synonyms: Acetic acid, phenylmethyl ester;Benzyl acetate (natural);NCI-C06508;Benzylester kyseliny octove [Czech];Phenylmethyl ethanoate;.alpha.-Acetoxytoluene;Acetic acid, benzyl ester;alpha-Acetoxytoluene;Phenylmethyl acetate;Benzyl ethanoate;Natural benzyl acetate;
EINECS: 205-399-7
Density: 1.055 g/cm3
Melting Point: -51 °C
Boiling Point: 213.5 °C at 760 mmHg
Flash Point: 102.2 °C
Solubility: practically insoluble in water
Appearance: clear colourless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 26.30000
LogP: 1.74970
Synthetic route
108-24-7

acetic anhydride

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
With iodine for 15h; Ambient temperature;100%
With magnesium(II) perchlorate at 20℃; for 0.25h;100%
With nickel dichloride for 0.116667h; microwave irradiation;100%
127-08-2

potassium acetate

100-44-7

benzyl chloride

140-11-4

Benzyl acetate

Conditions
ConditionsYield
Amberlyst A27 In toluene at 95℃; for 20h;100%
With dicyclohexano-18-crown-6 In acetonitrile at 60℃; for 0.5h; Product distribution; further reagents;85.4%
With zirconium (benzyldiethylammoniomethylphosphonate chloride) phosphate In water; toluene at 88℃; for 15h;82.5%
64-19-7

acetic acid

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
zirconium(IV) oxide In toluene for 1h; Heating; in vapor-phase at 150 deg C;100%
LaY zeolite at 116℃; for 8h; Acetylation;99%
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.25h;99%
127-08-2

potassium acetate

100-39-0

benzyl bromide

140-11-4

Benzyl acetate

Conditions
ConditionsYield
Sucrose-ethyleneoxide adducts In acetonitrile at 20℃; for 8h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;100%
With ammonium salt In neat (no solvent) for 2h; Ambient temperature;99%
With tetradecane; potassium acetate; magnetic nanoparticle-supported crown ether In toluene at 80℃; for 8h;96%
141-78-6

ethyl acetate

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate at 0℃; for 1h; Temperature; Inert atmosphere;100%
With heterogeneous zinc/imidazole catalyst at 90℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;99%
With C12F18O13Zn4 for 18h; Reflux; Inert atmosphere;98%
79-20-9

acetic acid methyl ester

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate at 0℃; for 1h; Temperature; Inert atmosphere; Molecular sieve;100%
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;95%
With 4 A molecular sieve; 1,3-di-tBu-2,3-dihydroimidazole carbene-polydimethylsiloxane at 20℃; for 6h;95%
104293-02-9

1-ethoxy-2-(trimethylsilyl)vinyl acetate

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 60℃; for 48h;100%
108-05-4

vinyl acetate

100-51-6

benzyl alcohol

A

140-11-4

Benzyl acetate

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
With 1,3-dicyclohexylimidazolium-2-thiocarboxylate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;A 100%
B n/a
With lipase from Pseudomonas Cepacia In benzene at 35℃; other ω-substituted-1-alkanols, var. solvents; kinetic parameters of transesterification;
108-05-4

vinyl acetate

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
Y5(OiPr)13O at 20℃; for 42h; Acetylation; transesterification;100%
With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;100%
With P(MeNCH2CH2)3N In tetrahydrofuran for 2h; Ambient temperature;99%
108-22-5

Isopropenyl acetate

100-51-6

benzyl alcohol

140-11-4

Benzyl acetate

Conditions
ConditionsYield
Y5(OiPr)13O at 20℃; for 1h; Acetylation; transesterification;100%
With indium(III) perchlorate; lithium perchlorate In ethyl acetate at 20℃; for 0.75h;99%
With iodine at 85 - 90℃; for 0.0833333h;98%
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Chemistry


IUPAC Name: Benzyl acetate 
Empirical Formula: C9H10O2
Molecular Weight: 150.1745
Canonical SMILES: CC(=O)OCC1=CC=CC=C1
InChI: InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChIKey: QUKGYYKBILRGFE-UHFFFAOYSA-N
EINECS: 205-399-7
Product Categories: FINE Chemical & INTERMEDIATES 
Water Solubility: <0.1 g/100 mL at 23 ºC 
Index of Refraction: 1.505
Molar Refractivity: 42.2 cm3
Molar Volume: 142.2 cm3
Surface Tension: 35.9 dyne/cm
Density: 1.055 g/cm3
Flash Point: 102.2 °C
Enthalpy of Vaporization: 44.98 kJ/mol
Boiling Point: 213.5 °C at 760 mmHg
Vapour Pressure: 0.164 mmHg at 25°C 
Appearance: Colorless liquid with an odor of pears.
Melting Point: -51 °C(lit.)
Classification Code of Benzyl acetate (CAS NO.140-11-4): Human Data; Mutation data; Skin / Eye Irritant; Tumor data

Uses

 Benzyl acetate (CAS NO.140-11-4) is used widely in perfumery and cosmetics for its aroma and in flavorings to impart apple and pear flavors. Benzyl acetate is commonly used as bait to attract and collect these bees for study. It is also used as a solvent in plastics and resin, cellulose acetate, nitrate, lacquers, oils,  polishes and inks.

Production

 Benzyl acetate (CAS NO.140-11-4) is prepared by esterification of benzyl alcohol, by heating with either an excess of acetic anhydride or acetic acid with mineral acids.
       C6H5CH2OH + CH3CO2H → C6H5CH2OCOCH3
The product is purified by treatment with boric acid and distilled to a purityIn excess of 98%.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LC50 inhalation 245ppm/8H (245ppm)   AMA Archives of Industrial Health. Vol. 21, Pg. 28, 1960.
cat LDLo skin 10gm/kg (10000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Journal of Pharmacology and Experimental Therapeutics. Vol. 84, Pg. 358, 1945.
guinea pig LD50 oral 2200mg/kg (2200mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(7), Pg. 17, 1985.
guinea pig LDLo subcutaneous 3gm/kg (3000mg/kg)   Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
human TCLo inhalation 50ppm (50ppm) BEHAVIORAL: ANTIPSYCHOTIC

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
"Handbook of Organic Industrial Solvents," 2nd ed., Chicago, National Assoc. of Mutual Casualty Companies, 1961Vol. 2, Pg. 31, 1961.
mouse LCLo inhalation 1300mg/m3/22H (1300mg/m3) BEHAVIORAL: GENERAL ANESTHETIC Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
mouse LD50 oral 830mg/kg (830mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(7), Pg. 17, 1985.
rabbit LD50 oral 2200mg/kg (2200mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(7), Pg. 17, 1985.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 11, Pg. 875, 1973.
rabbit LDLo subcutaneous 4gm/kg (4000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
rat LD50 oral 2490mg/kg (2490mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: 2810
WGK Germany: 1
RTECS: AF5075000

Specification

  Benzyl acetate (CAS NO.140-11-4), its Synonyms are Acetic acid, benzyl ester ; Acetic acid, phenylmethyl ester ; Benzyl ethanoate ; Benzylester kyseliny octove ; Phenylmethyl acetate ; Phenylmethyl ethanoate ; alpha-Acetoxytoluene .

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