Benzyl Benzoate

Product Name:

Benzyl benzoate

Synonyms:

N-tert-Butoxycarbonyl-L-aspartic Acid αBenzyl benzoate ReagentPlus(R), >=99.0%;Benzyl benzoate Vetec(TM) reagent grade, 98%;Benzoic acid benzyl ester≥ 99% (GC);VANZOATE(R);VENZONATE(R);Benylate;Benzyl alcohol benzoic ester

CAS:

120-51-4

MF:

C14H12O2

MW:

212.24

EINECS:

204-402-9

Product Categories:

Solvent;INORGANIC & ORGANIC CHEMICALS;Chemical -;Aromatic Esters;Piperazine derivates;organic chemical;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Vaccinium macrocarpon (Cranberry);CYSTADANE

Mol File:

120-51-4.mol

Melting point 

18 °C

Boiling point 

323-324 °C(lit.)

density 

1.118 g/mL at 20 °C(lit.)

vapor pressure 

1 mm Hg ( 125 °C)

refractive index 

n20/D 1.568(lit.)

FEMA 

2138 | BENZYL BENZOATE

FEMA 

2797 | OCTANAL

Fp 

298 °F

storage temp. 

2-8°C

solubility 

Miscible with ethanol, alcohol, chloroform, ether, oils.

form 

Liquid

color 

Clear colorless

Water Solubility 

practically insoluble

JECFA Number

24

Merck 

14,1127

BRN 

2049280

Stability:

Stable. Substances to be avoided include strong oxidizing agents. Combustible.

InChIKey

SESFRYSPDFLNCH-UHFFFAOYSA-N

CAS DataBase Reference

120-51-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzyl Benzoate(120-51-4)

EPA Substance Registry System

Benzyl benzoate (120-51-4)

Hazard Codes 

Xn,N

Risk Statements 

22-51/53

Safety Statements 

25-61-46

RIDADR 

UN 3082 9 / PGIII

WGK Germany 

2

RTECS 

DG4200000

Autoignition Temperature

896 °F

TSCA 

Yes

HazardClass 

9

HS Code 

29163100

Hazardous Substances Data

120-51-4(Hazardous Substances Data)

Toxicity

LD50 in rats, mice, rabbits, guinea pigs (g/kg): 1.7, 1.4, 1.8, 1.0 orally (Draize)

Description

Benzyl benzoate (BnBzO) is a mediation and insect repellent. It is one of the older preparation used to treat scabies which is a skin infections caused by the mite scarcoptes scabiei since it is lethal to the mite. It is capable of killing the mite in 5 minutes. It can also be used for the treatment of lice infestation of the head and the body. Its mechanism of action is through exerting toxic effect on the nervous system of the insects, further causing its death. It is also toxic to mite ova through an unknown mechanism. It can also be used as a repellent for chiggers, ticks, and mosquitoes as well as a dye carrier, solvent of cellulose derivatives, plasticizer, and a fixative.

Description

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5. This easily prepared compound with a mild balsamic odor has a variety of uses.

Chemical Properties

Benzyl Benzoate is the main component of Peru balsam oil. It occurs in fairly large amounts in a number of blossom concretes and absolutes (e.g., tuberose and hyacinth). It forms either a viscous liquid or solid flakes (mp 21–22°C) and has a weak, sweet, balsamic odor. It is prepared either by transesterification of technical methyl benzoate with benzyl alcohol or from benzyl chloride and sodium benzoate. A third process starts with benzaldehyde, which is converted in high yield into benzyl benzoate in the presence of sodium or aluminum benzylate (Tishchenko reaction). Benzyl benzoate is used in perfumery as a fixative and as a modifier in heavy blossom fragrances.

Chemical Properties

Colourless oily liquid with pleasant aromatic odour

Chemical Properties

Benzyl benzoate is a clear, colorless, oily liquid with a slightly aromatic odor. It produces a sharp, burning sensation on the tongue. At temperatures below 178℃ it exists as clear, colorless crystals.

Chemical Properties

Benzyl benzoate has a light, balsamic odor reminiscent of almond and a sharp, pungent taste.

Uses

benzyl benzoate is an anti-microbial. It can also act as a solvent, helping dissolve other substances in the product, and as a perfuming ingredient. It is the ester of benzyl alcohol and benzoic acid.

Uses

antiarteriosclerotic, hypolipaemic, hepatoprotectant

Uses

Benzyl Benzoate has seen use as an insecticide, as well as a solvent for various chemical reactions.

Uses

Used to kill lice and the mites responsible for the skin condition scabies.

Uses

As solvent of cellulose acetate, nitrocellulose and artificial musk; substitute for camphor in celluloid and plastic pyroxylin Compounds; perfume fixative; in confectionery and chewing gum flavors.

Production Methods

Benzyl benzoate is a constituent of Peru balsam and occurs naturally in certain plant species. Commercially, benzyl benzoate is produced synthetically by the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by the reaction of sodium benzylate with benzaldehyde.

Preparation

By the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of sodium benzylate on benzaldehyde.

Brand name

Pharmaceutic necessity for Dimercaprol [Injection]. Benylate (Sterling Winthrop).

Taste threshold values

Taste characteristics at 30 ppm: balsamic, fruity with powdery and berry nuances.

Hazard

Irritant to eyes, skin.

Contact allergens

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid. It is contained in Myroxylon pereirae and Tolu balsam. It is used in acaricide preparations against Sarcoptes scabiei or as a pediculicide. Direct contact may cause skin irritation, but rarely allergic contact dermatitis. As a fragrance allergen, benzyl benzoate has to be mentioned by name in EU cosmetics.

Chemical Synthesis

This colorless liquid is formally the condensation product of benzoic acid and benzyl alcohol. It can also be generated from benzaldehyde by the Tishchenko reaction.

storage

Benzyl benzoate is stable when stored in tight, well-filled, lightresistant containers. Exposure to excessive heat (above 408℃) should be avoided.

Incompatibilities

Benzyl benzoate is incompatible with alkalis and oxidizing agents.

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM injections and oral capsules). Included, as an active ingredient, in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Raw materials

Sodium-->Sodium carbonate-->Triethylamine-->Benzaldehyde-->Benzyl alcohol-->Benzoic acid-->Sodium benzoate-->Ethyl benzoate-->Peru balsam

Preparation Products

3-Phenoxybenzyl alcohol-->2,6-Dichloroaniline-->4-Cyanophenol-->Batyl alcohol-->Butethamine-->Disperse Yellow 126