Benzyl Alcohol

Base Information

• Chemical Name: Benzyl Alcohol
• CAS No.: 100-51-6
• Deprecated CAS: 1336-27-2,185532-71-2,2263936-23-6,2565578-76-7,185532-71-2
• Molecular Formula: C7H8O
• Molecular Weight: 108.14
• Hs Code.: 2906.29
• European Community (EC) Number: 202-859-9
• ICSC Number: 0833
• NSC Number: 760098,8044
• UNII: LKG8494WBH
• DSSTox Substance ID: DTXSID5020152
• Nikkaji Number: J4.009F
• Wikipedia: Benzyl alcohol
• Wikidata: Q52353
• NCI Thesaurus Code: C77028
• RXCUI: 1426
• Metabolomics Workbench ID: 38253
• ChEMBL ID: CHEMBL720
• Mol file: 100-51-6.mol

Synonyms:Alcohol, Benzyl;Benzenemethanol;Benzyl Alcohol

Chemical Property of Benzyl Alcohol

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 13.3 mm Hg ( 100 °C)
• Melting Point: -15 °C
• Refractive Index: 1.540
• Boiling Point: 204.7 °C at 760 mmHg
• PKA: 14.36±0.10(Predicted)
• Flash Point: 97.5 °C
• PSA: 20.23000
• Density: 1.047 g/cm³
• LogP: 1.17890
• Storage Temp.: 2-8°C
• Solubility.: H2O: 33 mg/mL, clear, colorless
• Water Solubility.: 4.29 g/100 mL (20 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 108.057514874
• Heavy Atom Count: 8
• Complexity: 55.4

Purity/Quality:

99% ^*data from raw suppliers

Benzyl Alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 20/22-63-43-36/37/38-23/24/25-45-40
• Safety Statements: 26-36/37-24/25-23-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C1=CC=C(C=C1)CO
• 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 aerosol is irritating to the eyes and skin. The substance may cause effects on the nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Chemical Composition and Properties: Benzyl alcohol is an aromatic alcohol consisting of benzene with a single hydroxymethyl substituent. It serves as a solvent, a metabolite, an antioxidant, and a fragrance. Benzyl alcohol, along with benzoic acid and its salts, and benzyl benzoate, are utilized in various cosmetic products as fragrance ingredients, pesticides, pH adjusters, preservatives, solvents, and viscosity-decreasing agents.
• Safety Assessment in Cosmetics: The Cosmetic Ingredient Review (CIR) has assessed the safety of benzyl alcohol, concluding that it is safe for use in cosmetic formulations at concentrations up to 5%, with hair dyes allowing concentrations up to 10%.
• Production Methods: Large-scale production of benzyl alcohol is achieved through the action of sodium or potassium carbonate on benzyl chloride.
• Selective Oxidation: Benzyl alcohol oxidation is a significant reaction in synthetic chemistry, particularly for producing benzaldehyde, which finds use in perfumery, dyestuff, and agrochemical industries. Traditionally, this oxidation process involves costly stoichiometric oxidants such as dichromate, chromic acid, and permanganate.
• Green Oxidation Processes: Environmental concerns have spurred the development of green oxidation processes for benzyl alcohol, aiming for high selectivity and reduced environmental impact. Photocatalytic conversion using materials like InZnS and CdS under anaerobic conditions shows promise, although selectivity for desired products remains an area for improvement.
• Medical Applications: Benzyl alcohol has FDA approval for use as a diluent in color additive mixtures for external drug use. It is used in the treatment of head lice infestation and scabies. Additionally, it serves as an antibacterial agent in pharmaceutical formulations for intravenous administration, including medications for critically ill neonates.

Technology Process of Benzyl Alcohol

There total 2188 articles about Benzyl Alcohol 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: 96.8%

benzaldehyde (100-52-7) + acetophenone (98-86-2) → 1-Phenylethanol (98-85-1,13323-81-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With sodium tetrahydroborate; tin(ll) chloride; In tetrahydrofuran; for 1.5h; Heating; selectivity, absence of SnCl₂, further solvents;

DOI:10.1246/cl.1987.853

Reference yield: 66.8%

toluene (108-88-3,15644-74-3,16713-13-6) → benzyl bromide (100-39-0) + benzaldehyde (100-52-7) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With air; hydrogen bromide; for 8h; Irradiation;

DOI:10.1246/bcsj.63.944

Reference yield: 66.0%

benzyl chloride (100-44-7) → benzyl 1-butyl ether (588-67-0) + benzyl bromide (100-39-0) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With cetyltrimethylammonim bromide; potassium bromide; In hexane; water; butan-1-ol; at 40 ℃; for 12h; microemulsion medium;

DOI:10.1016/S0040-4039(00)85678-6

upstream raw materials:

(E)-3-phenylpropenal

1-methyl-4-nitrosobenzene

n-butyl magnesium bromide

phosgene

Downstream raw materials:

diethylene glycol monobenzyl ether

2-Benzyloxyethanol

2-benzylthiophene

2,5-dibenzyl-thiophene

Refernces

• 1、 Maskill, H.,Jencks, William P.. "Nitrous Oxide as a Nucleophile in the Formation of a New Reactive Intermediate from Benzyl Cations in the Solvolysis of Benzyl Azoxytosylate". . p. 944 - 946. Retrieved 1984.
• 2、 Skonieczny, Janusz,Latos-Grazynski, Lechoslaw,Szterenberg, Ludmila. "Reactivity of silole within a core-modified porphyrin environment: Synthesis of 21-silaphlorin and its conversion to carbacorrole". . p. 4861 - 4874. Retrieved 2008.
• 3、 Misu, Yuhta,Togo, Hideo. "Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes". . p. 1342 - 1346. Retrieved 2003.
• 4、 Seuwen, P.,Warneck, P.. "Oxidation of toluene in NOx free air: product distribution and mechanism". . p. 315 - 332. Retrieved 1996.
• 5、 Jaita, Subin,Kaewkum, Pantitra,Duangkamol, Chuthamat,Phakhodee, Wong,Pattarawarapan, Mookda. "Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3". . p. 46947 - 46950. Retrieved 2014.
• 6、 Sugai, Tomoya,Usui, Shunme,Tsuzaki, Shun,Oishi, Hiroki,Yasushima, Daichi,Hisada, Shoko,Fukuyasu, Takahiro,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka. "Synthesis of β-hydroxy-α,α-disubstituted amino acids through the orthoamide-type overman rearrangement of an α,β-unsaturated ester and stereodivergent intramolecular SN2′ reaction: Development and application to the total synthesis of sphingofungin F". . p. 594 - 607. Retrieved 2018.
• 7、 Chaudhari, F. M.,Knox, G. R.,Pauson, P. L.. "-". . . Retrieved 1967.
• 8、 Maki et al.. "-". . p. 3295. Retrieved 1975.
• 9、 Dyer,Newborn. "-". . p. 5495,5496,5498. Retrieved 1958.
• 10、 Emayavaramban, Balakumar,Chakraborty, Priyanka,Sundararaju, Basker. "Cobalt-Catalyzed Reductive Alkylation of Amines with Carboxylic Acids". . p. 3089 - 3093. Retrieved 2019.