Benzyl formate

Base Information

• Chemical Name: Benzyl formate
• CAS No.: 104-57-4
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 2915.13
• European Community (EC) Number: 203-214-4
• NSC Number: 8049
• UNII: 79GJF97O0Y
• DSSTox Substance ID: DTXSID5059298
• Nikkaji Number: J53.979A
• Wikidata: Q4083784
• Metabolomics Workbench ID: 49384
• Mol file: 104-57-4.mol

Synonyms:benzyl formate

Chemical Property of Benzyl formate

Chemical Property:

• Appearance/Colour: Colorless Transparent Liquid
• Vapor Pressure: 0.273mmHg at 25°C
• Melting Point: 4ºC
• Refractive Index: 1.509 - 1.514
• Boiling Point: 203 °C(lit.)
• Flash Point: 180 °F
• PSA: 26.30000
• Density: 1.088 g/mL at 25 °C(lit.)
• LogP: 1.99550
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Insoluble in water, soluble in organic solvents, oils.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 95.4

Purity/Quality:

95%min ^*data from raw suppliers

Benzyl formate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R21/22:
• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 36-36/37-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC=O
• Uses: Solvent for cellulose esters; in perfumery.

Technology Process of Benzyl formate

There total 102 articles about Benzyl formate 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: 64.0%

phenylacetaldehyde (122-78-1) → benzyl formate (104-57-4) + benzaldehyde (100-52-7)

Guidance literature:

With Desulfoarculus baarsii superoxide reductase E₄₇A; dihydrogen peroxide; In acetonitrile; at 20 ℃; for 0.0333333h; pH=8.5; Reagent/catalyst; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c4cc06114d

Reference yield: 40.0%

N-methyl-N-phenylformamide (93-61-8) + benzyl alcohol (100-51-6,185532-71-2) → benzyl formate (104-57-4) + benzyl chloride (100-44-7)

Guidance literature:

N-methyl-N-phenylformamide; With Phthaloyl dichloride; In 1,4-dioxane; at 50 - 80 ℃; for 1h;

benzyl alcohol; In 1,4-dioxane; at 20 - 70 ℃; for 4h; Temperature;

Reference yield: 22.0%

benzyl chloride (100-44-7) → benzyl fluoride (350-50-5) + dibenzyl ether (103-50-4) + benzyl formate (104-57-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With potassium fluoride; formamide; tetrabutylammomium bromide; at 120 ℃; for 72h;

upstream raw materials:

formic acid

3-benzyloxy-2-methyl-butan-2-ol

benzyl bromide

formamide

Downstream raw materials:

N-benzylpyridin-2-amine

3-oxo-2-phthalimido-propionic acid benzyl ester

dichloromethyl benzyl ether

dibenzyl 4-methoxyphenylphosphonodithioate

Refernces

THE FRAGMENTATION OF BENZYLOXYCHLOROCARBENE: FORMATION OF BENZYL CATION

10.1016/S0040-4039(00)96022-2

The study investigates the thermal decomposition of 3-benzyloxy-3-chlorodiazirine in acetonitrile at 25°C to produce benzyloxychlorocarbene, which further fragments to form the benzyl cation. The researchers conducted a detailed analysis of the reaction, examining the effects of different solvents and solvent conditions on the fragmentation process. They found that the reaction proceeded cleanly in acetonitrile, with only minor solvent effects on the rate constant. The study also included an Arrhenius study to determine the energy of activation and a Hammett study to understand the reaction's sensitivity to substituent effects. The researchers proposed that the thermal fragmentation of benzyloxychlorocarbene yields intermediates such as ion pairs and suggested that the geometry of the diazirine prior to decomposition may influence the distribution of these ion pairs. Additionally, they explored the photolytic decomposition of the compound and observed the formation of benzyl radical, although they concluded that this was not the principal pathway for the fragmentation of the carbene. The study was supported by the National Science Foundation and contributed to the understanding of carbene chemistry and the formation of carbocations.