Benzyl Benzoate

Base Information

• Chemical Name: Benzyl Benzoate
• CAS No.: 120-51-4
• Molecular Formula: C14H12O2
• Molecular Weight: 212.248
• Hs Code.: 2916.31 DERIVATION
• European Community (EC) Number: 204-402-9
• ICSC Number: 0390
• NSC Number: 758204,8081
• UNII: N863NB338G
• DSSTox Substance ID: DTXSID8029153
• Nikkaji Number: J5.327I
• Wikipedia: Benzyl_benzoate
• Wikidata: Q413755
• NCI Thesaurus Code: C65255
• RXCUI: 19044
• Metabolomics Workbench ID: 42991
• ChEMBL ID: CHEMBL1239
• Mol file: 120-51-4.mol

Synonyms:Acaril;Acarosan;Ansar;Antiscabiosum;Ascabiol;Benzanil;Benzemul;benzyl benzoate;Benzylbenzoaat Smeersel FNA;Novoscabin

Chemical Property of Benzyl Benzoate

Chemical Property:

• Appearance/Colour: colourless oily liquid with pleasant aromatic odor
• Vapor Pressure: 0.00025mmHg at 25°C
• Melting Point: 18 °C
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 324.1 °C at 760 mmHg
• Flash Point: 147.9 °C
• PSA: 26.30000
• Density: 1.128 g/cm³
• LogP: 3.04360
• Water Solubility.: practically insoluble
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 213

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2
• Recent EU Clinical Trials: Investigation to assess the efficacy of topical benzyl benzoate 10/25% emulsion versus permethrin 5% creme for scabies treatment
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Chemical Properties: Benzyl benzoate (BB) is a benzoate ester formed by the condensation of benzoic acid with benzyl alcohol. It is a component of brown aromatic resin found in cinnamon oil and cough syrups and is widely utilized in the perfume, pharmaceutical, and food industries. Upon absorption, it undergoes hydrolysis to yield benzoic acid and benzyl alcohol.
• Medical Uses: Benzyl benzoate serves as an important anti-scabies agent and is effective against the mite Sarcoptes scabies, which causes scabies. It has also been used to treat lice infestations of the head and body. Although effective, its irritant properties make it less favorable as a treatment for scabies compared to other options.
• Production and Sustainability: Sustainable production processes for benzyl benzoate have been explored, including biocatalytic methods resulting in high purity. These processes offer favorable economic viability, making them suitable for industrial scale-up.
• Natural Occurrence: Benzyl benzoate is found in various plants and foods, including fruits, vegetables, herbs, and beverages such as tea and wine. It possesses a balsamic, herbal, and oily smell and occurs naturally in plants like babaco fruit, caper, and celery.
• Industrial and Environmental Considerations: Its low availability in nature necessitates chemical synthesis, but there is growing interest in developing sustainable production methods to meet industrial demand.
• Medical Applications: Benzyl benzoate is utilized in the treatment of conditions such as scabies, lice infestations, rosacea, and demodicosis. It acts as a medication for scabies and lice and as an insect repellent for various pests such as chiggers, ticks, and mosquitoes.
• Other Industrial Uses: In addition to its medical applications, benzyl benzoate finds use as a dye carrier, solvent, fixative, and camphor substitute in the perfume industry.

Technology Process of Benzyl Benzoate

There total 573 articles about Benzyl Benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.7%

benzyl alcohol (100-51-6,185532-71-2) → benzoic acid benzyl ester (120-51-4) + benzaldehyde (100-52-7)

Guidance literature:

With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate; In dichloromethane; water; at 20 - 25 ℃; for 1h;

DOI:10.1134/S1070363216110049

Reference yield: 88.0%

nitrobenzene (98-95-3,26969-40-4) + benzyl alcohol (100-51-6,185532-71-2) → N,N-dibenzylaniline (91-73-6) + benzoic acid benzyl ester (120-51-4) + benzaldehyde (100-52-7)

Guidance literature:

With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); 1,3-bis(mesityl)imidazolium chloride; at 150 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol1020527

Reference yield: 73.0%

benzyl alcohol (100-51-6,185532-71-2) → benzoic acid benzyl ester (120-51-4) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylhydroperoxide; C₅₆H₆₂Cl₂Mn₂N₆O₁₀P₂; In water; acetonitrile; at 80 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Time; Catalytic behavior; Green chemistry;

DOI:10.1002/ejic.201701064

upstream raw materials:

benzoic acid methyl ester

N,N'-dimethylbenzylamine

Benzyl acetate

sodium methylate

Downstream raw materials:

2-(benzylthio)imidazole

N-benzyl-2-pyridone

N-benzylpyridin-2-amine

benzamide

Refernces

• 1、 Dutta, Bishnu,Omar, Suheir,Natour, Suzana,Abu-Reziq, Raed. "Palladium nanoparticles immobilized on magnetic nanoparticles: An efficient semi-heterogeneous catalyst for carbonylation of aryl bromides". . p. 31 - 36. Retrieved 2015.
• 2、 Ooi, Takashi,Miura, Tomoya,Takaya, Keisuke,Maruoka, Keiji. "Catalytic, high-speed Tishchenko reaction using (2,7-dimethyl-1,8-biphenylenedioxy)bis(diisopropoxyaluminum) as a powerful bidentate catalyst". . p. 7695 - 7698. Retrieved 1999.
• 3、 Saegusa et al.. "". . p. 248. Retrieved 1969.
• 4、 Karthikeyan, Parasuraman,Bhagat, Pundlik Rambhau,Kumar, Sellappan Senthil,Muskawar, Prashant Narayan,Aswar, Sachin Arunrao. "Novel and efficient method for esterification catalyzed by 1-glycyl-3-methyl imidazolium chloride-iron (III) complex". . p. 983 - 990. Retrieved 2012.
• 5、 Daw, Prosenjit,Kumar, Amit,Espinosa-Jalapa, Noel Angel,Diskin-Posner, Yael,Ben-David, Yehoshoa,Milstein, David. "Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes". . p. 7734 - 7741. Retrieved 2018.
• 6、 Inoue, Toru,Takeda, Takanobu,Kambe, Nobuaki,Ogawa, Akiya,Ryu, Ilhyong,Sonoda, Noboru. "Synthesis of Thiol, Selenol, and Tellurol Esters from Aldehydes by the Reaction with i-Bu2AlYR (Y = S, Se, Te)". . p. 5824 - 5827. Retrieved 1994.
• 7、 Marvi,Fekri,Takhti. "Montmorillonite K10 and KSF clays as acidic and green catalysts for effective esterification of phenols and alcohols under MWI". . p. 1837 - 1840. Retrieved 2014.
• 8、 Touchy, Abeda S.,Kon, Kenichi,Onodera, Wataru,Shimizu, Ken-Ichi. "Unprecedented reductive esterification of carboxylic acids under hydrogen by reusable heterogeneous platinum catalysts". . p. 1499 - 1506. Retrieved 2015.
• 9、 Wu, Xiao-Feng,Yuan, Yang. "Synthesis of Esters from Stable and Convenient Sulfoxonium Precursors under Catalyst- And Additive-Free Conditions". . p. 1820 - 1824. Retrieved 2019.
• 10、 Frogneux, Xavier,Borondics, Ferenc,Lefran?ois, Stéphane,D'Accriscio, Florian,Sanchez, Clément,Carenco, Sophie. "Surprisingly high sensitivity of copper nanoparticles toward coordinating ligands: Consequences for the hydride reduction of benzaldehyde". . p. 5073 - 5080. Retrieved 2018.