100-44-7

Basic information

• Product Name: Benzyl chloride
• Synonyms: BENZYL CHLORIDE;A-CHLOROTOLUENE;ALPHA-CHLOROTOLUENE;AKOS BBS-00003953;(chloromethyl)-benzen;(Chloromethyl)benzene;(chloromethyl)-Benzene;1-Chloromethylbenzene
• CAS NO: 100-44-7
• Molecular Formula: C₇H₇Cl
• Molecular Weight: 126.58
• EINECS: 202-853-6
• Product Categories: Pharmaceutical Intermediates;Organics;Biochemistry;Reagents for Oligosaccharide Synthesis;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aryl;Building Blocks;C7;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;API Intermediate;alkyl chloride
• Mol File: 100-44-7.mol
• Article Data: 384

Chemical Properties

• Melting Point: -39 °C
• Boiling Point: 179 °C
• Flash Point: 165 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.1 g/mL at 25 °C(lit.)
• Vapor Density: 4.36 (vs air)
• Vapor Pressure: 10.3 mm Hg ( 60 °C)
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: 0-6°C
• Solubility: soluble0.46g/L at 30°C (Decomposes in contact with water)
• Explosive Limit: 1.1-14%(V)
• Water Solubility: 0.3 g/L (20 ºC)
• Stability: Unstable - inhibitors such as propylene oxide or trimethylamine are usually added to prevent polymerization. Combustible. Incomp
• Merck: 14,1129
• BRN: 471308
• CAS DataBase Reference: Benzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl chloride(100-44-7)
• EPA Substance Registry System: Benzyl chloride(100-44-7)

Safety Data

• 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
• RIDADR: UN 1738 6.1/PG 2
• WGK Germany: 3
• RTECS: XS8925000
• F: 8-19
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 100-44-7(Hazardous Substances Data)

Usage

Chemical Description

Benzyl chloride is a colorless liquid used in organic synthesis.

Chemical Description

Benzyl chloride is an organic compound that is used as a precursor to various chemicals, including benzyl alcohol.

InChI:InChI=1/C7H7Cl/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 56-23-5 tetrachloromethane 
• 80654-02-0 phosphorous acid benzyl ester-diphenyl ester 
• 128-09-6 N-chloro-succinimide 
• 108-88-3 toluene 
• 50-00-0 formaldehyd 
• 14070-51-0 N-chlorosaccharin 
• 103-50-4 dibenzyl ether 
• 15050-24-5 N-(benzyloxycarbonyl)glycyl chloride 
• 100-97-0 hexamethylenetetramine 
• 946-80-5 (benzyloxy)benzene 
• 120-51-4 benzoic acid benzyl ester 
• 4383-24-8 N,O-dibenzylhydroxylamine 
• 28643-58-5 benzyl-p-tolyl-carbamoyl chloride 
• 100375-51-7 benzyloxy-chloro-phenyl-borane 

Downstream Products

• 17229-17-3 benzyl 2-chloroethyl ether 
• 29897-82-3 N-benzylpyrrolidine 
• 2905-56-8 N-Benzylpiperidine 
• 774-91-4 1-benzyl-2-methylpyrrolidine 
• 409322-30-1 N-benzyl-N-nitro-toluene-4-sulfonamide 
• 1034-11-3 N,N'-dibenzylpiperazine 
• 55476-88-5 N-benzyl-N-methylmorpholinium chloride 
• 24417-01-4 7-Benzyl-7-aza-bicyclo[4.1.0]heptane 
• 61636-30-4 4-benzyl-2,6-dimethylmorpholine 
• 2116-65-6 4-benzyl pyridine 
• 101-82-6 2-Benzylpyridine 
• 620-95-1 3-benzylpyridine 
• 47090-47-1 2,6-dibenzylpyridine 
• 2876-13-3 N-benzylpyridinium chloride 

Relevant articles and documents

Photocatalytic oxidation of alkanes with dioxygen by visible light and copper(II) and iron(III) chlorides: Preference oxidation of alkanes over alcohols and ketones

Visible light irradiation of alkanes in acetonitrile with CuCl2 and FeCl3 catalysts under atmospheric dioxygen gave the corresponding alcohols and ketones effectively; in these reactions, the total selectivity of the products did not decrease so much with increase of alkane conversion. For example, cyclohexanol and cyclohexanone were formed with ca. 70% selectivity at 50% conversion, because overoxidation of the products took place more slowly than cyclohexane oxidation. The relative reactivity values of cycloalkanes increased as their ring-sizes decreased. In the oxidation of hexane, the reactivity ratio of C1-/C2-/C3-H was found to be 1.0/1.4/1.8 with CuCl2 and 1.0/4.6/6.6 with FeCl3, respectively. Toluene and diphenylmethane were more reactive than cyclohexane with FeCl3, as expected, whereas the alkane was oxidized faster than the benzylic compounds in the separate reaction with CuCl2. Moreover, the alkane oxidation could be comparably performed by sunlight instead of an artificial lamp.

Formation of Benzylic Chlorides by Rearrangement of Cycloheptatrienes with Tellurium Tetrachloride

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Vitamin B12 Catalyzed Atom Transfer Radical Addition

Vitamin B12, a natural Co-complex, catalyzes atom transfer radical addition (ATRA) of organic halides to olefins. The established conditions were found to be very selective, with atom transfer radical polymerization (ATRP) occurring only in the case of acrylates.

Investigation of the stability of the Corey-Kim intermediate

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Diphenylphosphinated Ethylene Oligomers as polymeric Reagents for Synthesis of Alkyl Chlorides from Alcohols

Diphenylphosphinated ethylene oligomers can be used as homogeneous polymeric reagents at 90 deg C in carbon tetrachloride to form alkyl chlorides from alcohols and since these funcionalized ethylene oligomers precipitate quantitatively from solution at 25 deg C, they can be easily recovered and separated from the reaction products and can be partially recycled.

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A convenient method for producing mono- and dichlorohydrins from glycerol

A new method for the transformation of glycerol into mono- and dichlorohydrins has been studied. With trimethylchlorosilane as chlorinating agent and acetic acid as catalyst, mono- and dichlorohydrins have been obtained in high yields and selectivity. In fact, under different reaction conditions, the synthesis of α-monochlorohydrin (3-chloropropan-1,2-diol) or α,γ-dichlorohydrin (1,3-dichloropropan-2-ol) as predominant product has been achieved. This process was also exploited for the valorisation of the crude mixture of glycerol and monochlorohydrin (glyceric mixture), a by-product from an earlier BioDiesel production. A reaction mechanism has been proposed based on investigations on the chlorination of different alcohols.

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Kinetic study of the reactions of chlorine atoms and Cl2.- radical anions in aqueous solutions. II. Toluene, benzoic acid, and chlorobenzene

The reactions of chlorine atoms and Cl2.- radical ions with toluene, benzoic acid, and chlorobenzene were studied using laser conventional flash photolysis of Na2S2O8 aqueous solutions containing Cl- ions. The reaction rate constants was diffusion-controlled, thus showed no dependence on the σ-Hammett parameter of the substituent in the aromatic ring. The high reactivity of Cl atoms was distinct with that of Cl2.- radical ions, for which the rate constants for the reactions with the substituted benzenes were -/M-sec. The π-complex of benzene yielded very low bond energies (a sequence of chemical reactions unless highly stabilized by the solvent. An electron-transfer reaction pathway was not important for the substrates benzene, toluene, and benzoic acid since phenolic derivatives formed from the disproportionation of HO-CHD radicals were not observed as reaction products. The dissimilarity in the behavior of the Cl-CHD radicals in the gas phase and in organic solvents compared with that in the aqueous phase seemed to be the lack of dissociation of Cl-CHD in aqueous solutions.

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The halogenation of aliphatic C-H bonds with peracetic acid and halide salts

Hydrocarbons react with molar concentrations of peracetic acid and halide salts to yield predominantly monohalogenated products under optimum conditions, with chlorination being more oxidatively efficient than bromination. The alkane halogenation proceeds at ambient temperature and does not require a heavy-metal catalyst. The observed reactivity is consistent with a radical mechanism, in which the peracid initially reacts with the halide ions to yield halogen-atom radicals, which ultimately oxidize the hydrocarbon. Although the reactivity proceeds slightly more efficiently in acetonitrile, the halogenation protocol works well in water.

Practical conversion of chlorosilanes into alkoxysilanes without generating HCl

Alcohol-free: A versatile, efficient, and practical synthesis of alkoxysilanes without generation of HCl involves the reaction of chlorosilanes with unsymmetrical ethers in the presence of a Lewis acid (see scheme). The reaction proceeds through selective cleavage of C-O bonds and is superior to conventional processes. Industrially feasible reagents are used and only one by-product results. Copyright

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BiCl3 : An efficient agent for selective chlorination of alcohols or for halogen exchange reaction

BiCl3 was found to be an effective reagent for an improved chlorination of alcohols and for a convenient halogen exchange reaction.

ESI-MS study on transient intermediates in the fast cyclopropenium- activated chlorination reaction of alcohols

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Thermal Decomposition of Allylbenzene Ozonide

Thermal decomposition of allylbenzene ozonide (ABO) at 98 deg C in the liquid phase yields toluene, bibenzyl, phenylacetaldehyde, formic acid, and (benzyloxy)methyl formate as major products; benzyl chloride is formed when chlorinated solvents are employe

The chemistry of cyclic carbaphosphazenes: The first observation of (R 2PN)(ClCN)2 (R=Cl, Ph) as a reagent for the conversion of alcohols to aldehydes, ketones, and alkyl chlorides

The oxidation of nine primary and secondary alcohols to the corresponding aldehydes and ketones has been carried out under mild conditions and in good yields using the cyclocarbaphosphazenes (R2PN)(ClCN)2 [R2P = Cl2 P(1), Ph2P(2)] along with dimethylsulfoxide. While both the P-Cl and C-Cl bonds of the carbaphosphazene can in principle bring about the reaction, we observed an increased preference for the C-Cl bonds over the P-Cl bonds in the oxidation of alcohol. Blocking the reactive P site on the heterocyclic ring with the phenyl groups was found to reduce the yields of the oxidized products, while blocking the C- sites with diethylamino groups resulted in no reaction. In addition, along with DMF, the same cyclocarbaphosphazene has been found to be useful for the conversion of alcohols to alkyl chlorides. Copyright Taylor & Francis Group, LLC.

Discovery of novel quinazolinone derivatives as potential anti-HBV and anti-HCC agents

As a continuation of earlier works, a series of novel quinazolinone derivatives (5a-s) were synthesized and evaluated for their in vitro anti-HBV and anti-hepatocellular carcinoma cell (HCC) activities. Among them, compounds 5j and 5k exhibited most potent inhibitory effect on HBV DNA replication in both drug sensitive and resistant (lamivudine and entecavir) HBV strains. Interestingly, besides the anti-HBV effect, compound 5k could significantly inhibit the proliferation of HepG2, HUH7 and SK- cells, with IC50 values of 5.44, 6.42 and 6.75 μM, respectively, indicating its potential anti-HCC activity. Notably, the in vitro anti-HCC activity of 5k were more potent than that of positive control 5-fluorouracil and sorafenib. Further studies revealed that compound 5k could induce HepG2 cells apoptosis by dose-dependently upregulating Bad and Bax expression and decreasing Bcl-2 and Bcl-xl protein level. Considering the potent anti-HBV and anti-HCC effect, compound 5k might be a promising lead to develop novel therapeutic agents towards HBV infection and HBV-induced HCC.

Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate

Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.

Thiourea-Mediated Halogenation of Alcohols

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.