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Structure of the chloromethyl group. In organic chemistry, the chloromethyl group is a functional group that has the chemical formula −CH 2 −Cl. The naming of this group is derived from the methyl group (which has the formula −CH 3), by replacing one hydrogen atom by a chlorine atom. Compounds with this group are a subclass of the ...
The Blanc chloromethylation (also called the Blanc reaction) is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride to form chloromethyl arenes. The reaction is catalyzed by Lewis acids such as zinc chloride. [1] The reaction was discovered by Gustave Louis Blanc (1872-1927) in 1923. [2] [3] Blanc chloromethylation
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: [3] C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl. In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. [4]
The structure of xylylene dichloride is characterized by an benzene ring with two chloromethyl groups and four hydrogen atoms bound to it. [4] The chloromethyl groups can be located on different sites on the ring, leading to a few different possible forms. These forms are: [3] o-xylylene dichloride: 1,2-bis(chloromethyl)benzene
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C 6 H 5 Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2. The reaction is proposed to proceed via a substitution nucleophilic internal mechanism. [3]
For example, the industrial production of chloroethane proceeds by the reaction of ethylene with HCl: H 2 C=CH 2 + HCl → CH 3 CH 2 Cl. In oxychlorination, hydrogen chloride instead of the more expensive chlorine is used for the same purpose: CH 2 =CH 2 + 2 HCl + 1 ⁄ 2 O 2 → ClCH 2 CH 2 Cl + H 2 O.
Chloromethyl methyl ether (CMME) is a compound with formula CH 3 OCH 2 Cl. A colorless liquid, it is a chloroalkyl ether.It is used as an alkylating agent.In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group, [3] and is thus often called MOM-Cl or MOM chloride.