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%min ^*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.
• Uses: Benzyl alcohol is a colorless clear oily liquid; its odor type is floral and its odor at 100% is described as 'floral rose phenolic balsamic'.Benzyl alcohol is used in cosmetics as afragrance component, preservative, solvent and diluting agent for perfumes and flavors, and viscosity-decreasing agent. It is used as a solvent for surface-coating materials, cellulose esters and ethers, alkyd resins,acrylic resins, fats, dyestuffs,casein (when hot), gelatin, shellac and waxes. It is added in small amounts to surface-coating materials to improve their flow and gloss. In the textile industry, benzyl alcohol is used as anauxiliary in the dyeing of wool, polyamides, and polyesters. In pharmacy it is used as a local anesthetic ingredient in over-the-counter anorectal, oral healthcare and topical analgesic drug products and, because of its antimicrobial effect, as an ingredient of ointments and other preparations (U.S. National Library of Medicine).Benzyl alcohol is also a starting material for the preparation of numerous benzyl esters that are used as odorants, flavors, stabilizers for volatile perfumes, and plasticizers and is also employed in the extractive distillation of m- and p-xylenes and m- and p-cresols. Other uses include or have included heat-sealing of polyethylene films,in color photography as a development accelerator and in microscopy as embedding material (U.S.National Library of Medicine). Esters of benzyl alcohol are used in makingperfume, soap, flavoring, lotion, and ointment.It finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.It occurs in natural products such as oils ofjasmine and castoreum. Benzyl alcohol is widely used as a solvent for the dielectrophoretic reconfiguration of nanowires, inks, paints, lacquers and epoxy resin coatings and as a precursor to a variety of esters used in soaps, perfumes and flavoring. It is employed as a local anesthetic which reduces the pain associated with lidocaine injection. It has a various applications in baby products, bath products, soaps and detergents, eye makeup, blushers, cleansing products, make up products as well as hair, nail and skin care products. benzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.
• Production Method: 1.Benzyl chloride with potassium or sodium is heated for a long timg, and hydrolyzes to yield benzyl alcohol. 2.Benzaldehyde in methanol and sodium hydroxide solution react to benzyl alcohol at 65~75 ℃. The product has high purity. 3.Using benzyl chloride as raw materials, it is heated and hydrolyzes to yield benzyl alcohol in the presence of the sodium catalyst. Specification of spices benzyl alcohol(QB792-81): the relative density of 1.041-1.046; refractive index of 1.538-1.541; boiling range 203-206℃ and distillate volume more than 95%; dissolving completely in 30 volumes of distilled water; containing more than 98 percent of alcohol; chlorine test (NF) as the side reaction. Raw material consumption quota: benzyl chloride 1600kg/t; soda ash 1000kg/t. 4.Benzyl alcohol exists naturally in orange flower, ylang-ylang, jasmine, gardenia, acacia, lilac and hyacinth. Benzyl chloride or benzaldehyde is used as raw materials to prepare benzyl alcohol in the industry. 5.Add chlorobenzyl to 12% sodium carbonate solution, heat to 93 ℃ and stir for 5h. Then warm the mixture to 101~103℃ and react for 10h. After the reaction, cool it to the room temperature, and add salt to saturation. After still standing for stratification, take the upper liquid and get crude products through pressure distillation. Then refine to gain the target products. The yield is 70%～72%. C6H5CH2Cl+H2O[Na2CO3]→C6H5CH2OH+NaCl+CO2↑ In the presence of sodium hydroxide, formaldehyde and benzaldehyde react to produce benzyl alcohol by disproportionation reaction. C6H5CHO+HCHO[NaOH]→C6h5CH2OH+HCOONa
• Description: Benzyl alcohol is a component catalyst for epoxy resins. It is also contained in the color developer C-22.
• Physical properties: Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor threshold concentration in water is 10 ppm (Buttery et al., 1988).

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%

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-phenylethanol

2-benzylthiophene

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.