3D Mol Similar

Benzyl acetate

Iupac Name：benzyl acetate

CAS No.: 140-11-4

Molecular Weight：150.177

Modify Date.: 2022-11-16 18:03

Introduction: In perfumery, solvent for cellulose acetate and nitrate. View more+

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1. Names and Identifiers

1.1 Name: Benzyl acetate
1.2 Synonyms: Acetic acid benzyl ester Acetic acid phenylmethyl ester Acetic acid, phenylmethyl ester acetoxymethylbenzene alpha-Acetoxytoluene Bentyl acetate Benzenemethanol acetate Benzenemethanol ethanoate Benzul acetate Benzyiacetate Benzyl Acetate 140-11-4 benzyl acetater Benzyl alcohol acetate Benzyl Alcohol Impurity 1 Benzyl Alcohol Impurity D Benzyl ester of acetic acid Benzyl ethanoate Benzylacetat Benzylester kyseliny octove benzyloxyacetoaldehyde EINECS 205-399-7 Ethanoic acid phenylmethyl ester FEMA 2135 MFCD00008712 phenylmethyl acetate Phenylmethyl ethanoate Plastolin I

1.3 CAS No.: 140-11-4

1.4 CID: 8785

1.5 EINECS(EC#): 205-399-7

1.6 Molecular Formula: C9H10O2 (isomer)

1.7 Inchi: InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

1.8 InChkey: QUKGYYKBILRGFE-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(=O)OCC1=CC=CC=C1

1.10 Isomers Smiles: CC(=O)OCC1=CC=CC=C1

2. Properties

2.1 Density: 1.055

2.1 Melting point: -51℃

2.1 Boiling point: -60.7° F (NTP, 1992)

2.1 Refractive index: 1.501-1.503

2.1 Flash Point: 195° F (NFPA, 2010)

2.2 Precise Quality: 150.06800

2.2 PSA: 26.30000

2.2 logP: 1.74970

2.2 Solubility: <0.1 g/100 mL at 23 ºC

2.3 VaporDensity: 5.1 (AIR= 1)

2.4 AnalyticLaboratory Methods: GC with FID or MS has been used to analyze for benzyl acetate; in volatile mixtures.

2.5 Appearance: Colorless liquid with an odor of pears.

2.6 AutoIgnition: 862° F (NTP, 1992)

2.7 Storage: Benzyl acetate should be kept stored in a cool, dry place with the container closed when not in use.

2.8 Carcinogenicity: Not listed by ACGIH, IARC,NTP, or California Proposition 65.

2.9 Chemical Properties: Benzyl acetate is a colorless liquid with a fruity odor. On burning and decomposition, it produces irritating fumes. Benzyl acetate reacts with strong oxidants causing fire and explosion hazard.

2.10 Color/Form: WATER-WHITE LIQUID

2.11 Decomposition: When heated to decomposition it emits irritating fumes.

2.12 Odor: PEAR-LIKE ODOR

2.13 Physical: BENZYL ACETATE; is a colorless liquid with an odor of pears. (USCG, 1999)

2.14 Water Solubility: <0.1 g/100 mL at 23 oC

2.15 Spectral Properties: INDICES OF REFRACTION: 1.5232 @ 20 DEG C/D; 1.4998 @ 25 DEG C/D
IR: 3715 (Coblentz Society Spectral Collection)
UV: 260 (Sadtler Research Laboratories Spectral Collection)
NMR: 53 (Varian Associates NMR Spectra Catalogue)
MASS: 879 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
IR: 2:892C (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 7:21A (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 4147 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

2.16 Stability: Stable under normal temperatures and pressures.

2.17 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The acetate ester of benzyl alcohol.

3.2 General Description: Colorless liquid with an odor of pears.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1368 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 503 of 1368 companies. For more detailed information, please visit ECHA C&L website

Of the 14 notification(s) provided by 865 of 1368 companies with hazard statement code(s):

H319 (10.06%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H412 (89.83%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P273, P280, P305+P351+P338, P337+P313, and P501

3.4 Methods of Manufacturing: BY INTERACTION OF BENZYL CHLORIDE; & SODIUM ACETATE;; BY ACETYLATION OF BENZYL ALCOHOL;; OR FROM BENZALDEHYDE; & ACETIC ACID; WITH ZINC; DUST.

3.5 Produe Method: Benzyl acetate is produced by the interaction of benzylchloride and sodiumacetate, by acetylation of benzyl alcohol,or from benzaldehyde and acetic acid with zinc dust .

3.6 Purification Methods: Purify the acetate by fractional distillation, preferably in a good vacuum. Values of n25 of 1.5232-1.5242 are too high and should be nearer to 1.4994. [Merker & Scott J Org Chem 26 5180 1961, Beilstein 6 IV 2262.]

3.7 Usage: In perfumery, solvent for cellulose acetate and nitrate.

4. Safety and Handling

4.1 Symbol: ;

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Exposure Standards and Regulations: Benzyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Synthetic flavoring substances and adjuvants incl benzyl acetate may be safely used in foods.

4.2 Packing Group: Z01

4.2 Octanol/Water Partition Coefficient: log Kow = 1.96

4.3 Fire Hazard: Benzyl acetate is combustible.

4.4 Other Preventative Measures: 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.

4.5 Hazard Declaration: H412

4.5 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.6 RIDADR: 2810

4.6 Fire Fighting Procedures: ALCOHOL FOAM, CARBON DIOXIDE.

4.7 FirePotential: Combustible liquid.

4.8 Safety Profile: A poison by inhalation.Moderately toxic by ingestion and subcutaneous routes.Human systemic effects by inhalation: an antipsychotic,unspecified respiratory and urinary system effects.Questionable carcinogen with experimental tumorigenicdata. Combusti

4.9 Formulations/Preparations: FREE FROM CHLORINE GRADE WHICH SHOULD HAVE ESTER CONTENT OF 97% BUT FOR WHICH LOWER GRADE MATERIAL IS SOMETIMES SUBSTITUTED; TECHNICAL GRADE WHICH IS NOT FREE FROM CHLORINE & FOR WHICH ESTER CONTENT VARIES CONSIDERABLY; "FOOD CHEMICALS CODEX".

4.10 WGK Germany: 1

4.10 RTECS: AF5075000

4.10 Protective Equipment and Clothing: ... Irritating to skin, eyes, respiratory tract.

4.11 Skin, Eye, and Respiratory Irritations: ... Irritating to skin, eyes, respiratory tract.

4.12 Safety: Hazard Codes:?Xi
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

4.13 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 .

4.14 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P273 Avoid release to the environment.
Response	none
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

1H NMR : in CDCl3

Predict 1H proton NMR

gas

IR : liquid film

LIQUID 99% PURE

SOLUTION (10% CCl4 FOR 3800-1340, 10% CS2 FOR 1340-450 CM-1)

Raman : 4880 A,100M,liquid

Mass

7. Synthesis Route

140-11-4Total: 96 Synthesis Route

108-88-3

140-11-4 293 Suppliers

100-51-6 837 Suppliers

Literatures:
Eberson, Lennart; Wistrand, Lars-Goeran Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1980 , vol. 34, # 5 p. 349 - 358
Yield: ~2%

100-44-7 207 Suppliers

140-11-4 293 Suppliers

767-90-8 7 Suppliers

100-51-6 837 Suppliers

Literatures:
Journal fuer Praktische Chemie (Leipzig), , vol. <2> 39, p. 175 Justus Liebigs Annalen der Chemie, , vol. 96, p. 246
Yield: null

103-82-2

553-86-6 97 Suppliers

140-11-4 293 Suppliers

102-16-9 48 Suppliers

100-52-7 271 Suppliers

Literatures:
Fukagawa, Toshihiro; Fujiwara, Yuzo; Taniguchi, Hiroshi Journal of Organic Chemistry, 1982 , vol. 47, # 12 p. 2491 - 2493
Yield: ~17%

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8. Precursor and Product

precursor:

93-58-3

100-51-6

80953-51-1

75-36-5

80326-66-5

78-39-7

774-48-1

103-50-4

141-78-6

5437-45-6

23556-91-4

76246-96-3

93-97-0

71-43-2

3864-15-1

37003-25-1

33817-94-6

100-46-9

100-44-7

64-19-7

2550-26-7

View all

product :

539-30-0

100-51-6

22767-96-0

1135-39-3

103-50-4

77376-01-3

141-78-6

831-91-4

538-86-3

42998-51-6

620-79-1

120-51-4

142-26-7

21388-97-6

46854-91-5

81171-44-0

621-82-9

82166-21-0

103-29-7

937-55-3

79-20-9

619-90-9

5396-89-4

100-41-4

View all

9. Other Information

9.0 Usage: Benzyl acetate can be used as a high boiling point solvent in coatings, like ink coating, binding agent and paint remover. It is used in soap and other chemical essences and has the effect of promote in floral and fantasy essences in jasmine, white orchid, fragrant plantain lily, gekkakou, narcissus and other essences. It is a plasticizer for ionophore membranes.

9.1 Merck: 14,1123

9.2 BRN: 1908121

9.3 Chemical Properties: Benzyl acetate is a colorless liquid with a fruity odor. On burning and decomposition, it produces irritating fumes. Benzyl acetate reacts with strong oxidants causing fire and explosion hazard.

Benzyl acetate is stable under normal conditions of use. Heating to decomposition may release carbon monoxide, carbon dioxide and other potentially toxic fumes and gases. Vapors may form explosive mixtures with air at elevated temperatures (> 90°C / 194°F). Avoid heat, open flames and other potential sources of ignition.
It has been used as a food additive in fruit flavours and as a component of perfumes since the early 1990s and is widely used as a fragrance in soaps, detergents and incense. There is widespread human exposure to benzyl acetate by ingestion, skin application and inhalation.

9.4 Chemical Properties: Benzyl acetate has a characteristic flowery (jasmine) odor and a bitter, pungent taste. It is the main component of jasmine absolute and gardenia oils. It occurs as a minor component in a large number of other essential oils and extracts. It is a colorless liquid with a strong, fruity, jasmine odor. Benzyl acetate is prepared by esterification of benzyl alcohol with acetic anhydride (e.g., with sodium acetate as a catalyst) or by reaction of benzyl chloride with sodium acetate. In terms of volume, benzyl acetate is one of the most important fragrance and flavor chemicals.Although benzyl acetate is present in some essential oils at levels up to 65%, most of the commercial product is of synthetic origin.

9.5 Occurrence: Present as a main constituent in several oils and flower absolutes: ylang-ylang, cananga, neroli, jasmine, hyacinth, gardenia, tuberose. It has been isolated from the essential oil of the flowers of Loiseleuria procumbens Desv. (azelea). Also reported found in apricot, cooked asparagus, mozzarella cheese, grilled beef, cooked pork, malt whiskey, fresh mango, malt, wort and clams.

9.6 Uses: In perfumery, solvent for cellulose acetate and nitrate.

9.7 Uses: Benzyl acetate is used as an artificial jasmine and other perfumes, soap perfume, flavoring agent, solvent for cellulose acetate and nitrate, natural and synthetic resins, oils, lacquers, polishes, printing inks, and varnish removers.

9.8 Preparation: By interaction of benzyl chloride and sodium acetate; by acetylation of benzyl alcohol, or from benzaldehyde and acetic acid with zinc dust.

9.9 Definition: ChEBI: The acetate ester of benzyl alcohol.

9.10 Production Methods: Benzyl acetate is produced by the interaction of benzyl chloride and sodiumacetate, by acetylation of benzyl alcohol, or from benzaldehyde and acetic acid with zinc dust .

9.11 Aroma threshold values: Detection: 2 to 270 ppb

9.12 Taste threshold values: Taste characteristics at 40 ppm: sweet and fruity

9.13 Synthesis Reference(s): Chemical and Pharmaceutical Bulletin, 35, p. 1608, 1987 DOI: 10.1248/cpb.35.1608
The Journal of Organic Chemistry, 31, p. 2033, 1966 DOI: 10.1021/jo01344a544
Synthetic Communications, 24, p. 1045, 1994 DOI: 10.1080/00397919408020781

9.14 General Description: Colorless liquid with an odor of pears.

9.15 Air & Water Reactions: Insoluble in water.

9.16 Reactivity Profile: Benzyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Benzyl acetate is incompatible with strong oxidizing agents. Benzyl acetate is also incompatible with acids, bases and reducing agents.

9.17 Hazard: A poison by inhalation. Moderately toxic by ingestion. Combustible. Upper respiratory tract irritant. Questionable carcinogen.

9.18 Health Hazard: Harmful if inhaled. May be harmful if swallowed or absorbed through the skin. Vapor or mist is irritating to the eyes, mucous membrane and upper respiratory tract.

9.19 Health Hazard: Exposures to benzyl acetate cause adverse health effects. The symptoms of toxicity and poisoning include irritation to the skin, eyes, burning sensation, confusion, dizziness, drowsiness, labored breathing, sore throat, nausea, vomiting, and diarrhea. Benzyl acetate also causes adverse health effects to the respiratory tract and the CNS system with neurological effects.

9.20 Fire Hazard: Benzyl acetate is combustible.

9.21 Safety Profile: A poison by inhalation.Moderately toxic by ingestion and subcutaneous routes.Human systemic effects by inhalation: an antipsychotic,unspecified respiratory and urinary system effects.Questionable carcinogen with experimental tumorigenicdata. Combusti

9.22 Carcinogenicity: Not listed by ACGIH, IARC, NTP, or California Proposition 65.

9.23 Metabolism: The esters of benzyl alcohol, such as the acetate, benzoate, cinnamate and hydrocinnamate, are rapidly hydrolysed in vivo to benzyl alcohol which is then oxidized to benzoic acid and excreted as hippuric acid

9.24 storage: Benzyl acetate should be kept stored in a cool, dry place with the container closed when not in use.

9.25 Purification Methods: Purify the acetate by fractional distillation, preferably in a good vacuum. Values of n25 of 1.5232-1.5242 are too high and should be nearer to 1.4994. [Merker & Scott J Org Chem 26 5180 1961, Beilstein 6 IV 2262.]

9.26 Precautions: Exposures to benzyl acetate far above the OEL may result in unconsciousness. After handling and using benzyl acetate, workers should wash thoroughly and remove contaminated clothing, washing it before reuse. Workers should avoid any kind of contact of benzyl acetate with the eyes, skin, ingestion, and inhalation. Workers should wear safety glasses and chemical goggles to avoid splashing of the chemical substance during work, and wear appropriate protective gloves and clothing to prevent skin exposure

9.27 Physical properties: Benzyl acetate has a characteristic flowery (jasmine) odor and a bitter, pungent taste. It is the main component of jasmine absolute and gardenia oils. It occurs as a minor component in a large number of other essential oils and extracts. It is a colorless liquid with a strong, fruity, jasmine odor. In terms of volume, benzyl acetate is one of the most important fragrance and flavor chemicals. Although benzyl acetate is present in some essential oils at levels up to 65%, most of the commercial product is of synthetic origin.

9.28 Definition: ChEBI: Benzyl acetate is the acetate ester of benzyl alcohol. It has a role as a metabolite. It is an acetate ester and a benzyl ester.

9.29 Flammability and Explosibility: Nonflammable

10. Computational chemical data

Molecular Weight: 150.177g/mol
Molecular Formula: C₉H₁₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 150.068079557
Monoisotopic Mass: 150.068079557
Complexity: 126
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 26.3
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADACgmAIyCIAABACIAiDSCAACAAAgAAAIiAAACIgIJiKAMRiCMAAkwAEIqAeAwCAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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