Benzyl Chloride

Base Information

• Chemical Name: Benzyl Chloride
• CAS No.: 100-44-7
• Molecular Formula: C7H7Cl
• Molecular Weight: 126.586
• Hs Code.: 29039990
• European Community (EC) Number: 905-236-6,202-853-6
• ICSC Number: 0016
• NSC Number: 8043
• UN Number: 1738
• UNII: 83H19HW7K6
• DSSTox Substance ID: DTXSID0020153
• Nikkaji Number: J4.007J
• Wikipedia: Benzyl_chloride
• Wikidata: Q412260
• NCI Thesaurus Code: C77455
• Metabolomics Workbench ID: 52782
• ChEMBL ID: CHEMBL498878
• Mol file: 100-44-7.mol

Synonyms:alpha-chlorotoluene;benzyl chloride;benzyl chloride, 14C-labeled

Chemical Property of Benzyl Chloride

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 10.3 mm Hg ( 60 °C)
• Melting Point: -39 °C
• Refractive Index: n20/D 1.538(lit.)
• Boiling Point: 179.399 °C at 760 mmHg
• Flash Point: 73.889 °C
• PSA: 0.00000
• Density: 1.018 g/cm³
• LogP: 2.42540
• Storage Temp.: 0-6°C
• Solubility.: soluble0.46g/L at 30°C (Decomposes in contact with water)
• Water Solubility.: 0.3 g/L (20 ºC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 126.0236279
• Heavy Atom Count: 8
• Complexity: 55.4
• Transport DOT Label: Poison Corrosive

Purity/Quality:

98% or more ^*data from raw suppliers

Benzyl Chloride (stabilized with epsilon-Caprolactam) >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,T+
• Statements: 45-22-23-37/38-41-48/22-43-26-46
• Safety Statements: 53-45-36/37/39-28-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)CCl
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C , on spraying much faster.
• Effects of Short Term Exposure: The substance is corrosive to the eyes. The vapour is irritating to the eyes, skin and respiratory tract. Inhalation of the vapour or aerosol may cause lung oedema. The substance may cause effects on the central nervous system. This may result in unconsciousness.
• Effects of Long Term Exposure: The substance may have effects on the liver and kidneys. This may result in tissue lesions. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Physical properties: Colorless to pale yellowish-brown liquid with a pungent, aromatic, irritating odor. Odor threshold concentration is 47 ppbv (Leonardos et al., 1969). Katz and Talbert (1930) reported an experimental detection odor threshold concentration of 210 μg/m3 (41 ppbv). The solubility of benzyl chloride in water is 0.33 g/L at 4°C, 0.49 g/L at 20°C, and 0.55 g/L at 30°C. It is freely soluble in chloroform, acetone, acetic acid esters, diethyl ether, and ethyl alcohol.
• Uses: Benzyl chloride is used in the manufacture of benzyl Compounds, dyes, artificial resins, tanning agents, phar maceuticals, plasticizers, synthetic tannins, perfumes, lubricants, and quaternary ammonium compounds. It is also an intermediate in the preparation of phenylacetic acid (precursor to phamaceuticals).

Technology Process of Benzyl Chloride

There total 608 articles about Benzyl Chloride 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: 90%

toluene (108-88-3,15644-74-3,16713-13-6) → benzyl bromide (100-39-0) + benzyl chloride (100-44-7)

Guidance literature:

With tetrabutylammomium bromide; hydrogen bromide; potassium bromide; In water; at 20 ℃; Irradiation; Green chemistry;

DOI:10.1039/c8gc02628a

Reference yield: 86%

(benzyloxy)benzene (946-80-5) → benzyl chloride (100-44-7) + phenol (108-95-2,27073-41-2)

Guidance literature:

With water; boron trichloride; In chloroform-d1; at 20 ℃;

Reference yield: 82%

5,10,15,20-tetramesitylporphyrin?manganese(IV)-oxo (115775-87-6) + dichloromethane (75-09-2) + toluene (108-88-3,15644-74-3,16713-13-6) → {(5,10,15,20-tetrakis(2,4,6-trimethylphenyl)porphyrinate)Mn(III)}(1+) + benzyl chloride (100-44-7)

Guidance literature:

at -10 ℃; Kinetics; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.9b04496

upstream raw materials:

tetrachloromethane

phosphorous acid benzyl ester-diphenyl ester

N-chloro-succinimide

toluene

Downstream raw materials:

benzyl 2-chloroethyl ether

N-benzylpyrrolidine

N-Benzylpiperidine

1-benzyl-2-methylpyrrolidine

Refernces

• 1、 Wang, Yun,Xi, Yanli. "An experimental and theoretical study on imidazolium-based ionic liquid promoted chloromethylation of aromatic hydrocarbons". . p. 2196 - 2199. Retrieved 2013.
• 2、 Venkana, Purugula,Kumar, Mukka Satish,Rajanna, Kamatala Chinna,Ali, Mir Moazzam. "Trichloroisocynuric acid/DMF as efficient reagent for chlorodehydration of alcohols under conventional and ultrasonic conditions". . p. 97 - 103. Retrieved 2015.
• 3、 Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong. "Chloroalkylation of aryl aldehydes using alkylboron dichlorides in the presence of oxygen". . p. 6239 - 6241. Retrieved 2001.
• 4、 Huyser. "-". . p. 5246. Retrieved 1960.
• 5、 Bortoluzzi, Marco,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano. "Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study". . p. 3169 - 3177. Retrieved 2016.
• 6、 Muathen, Hussni A.. "Chlorination of aromatic compounds with chlorous acid under non-aqueous conditions". . p. 1493 - 1497. Retrieved 1999.
• 7、 Yin, Haolin,Jin, Yi,Hertzog, Jerald E.,Mullane, Kimberly C.,Carroll, Patrick J.,Manor, Brian C.,Anna, Jessica M.,Schelter, Eric J.. "The Hexachlorocerate(III) Anion: A Potent, Benchtop Stable, and Readily Available Ultraviolet A Photosensitizer for Aryl Chlorides". . p. 16266 - 16273. Retrieved 2016.
• 8、 Barton, Derek H.R.,Launay, Franck. "The selective functionalization of saturated hydrocarbons. Part 47, investigation of the size of the reagent involved in the Fe(II)-Fe(IV) manifold". . p. 12699 - 12706. Retrieved 1998.
• 9、 Schreyer. "-". . p. 3483. Retrieved 1958.
• 10、 Gruber, Heinrich,Greber, Gerd. "Phase Transfer Catalysts Based on Sucrose Ethyleneoxide Adducts". . p. 1063 - 1076. Retrieved 1981.