Chloromethyl phenyl

Chemical Designations - Synonyms Phenacyl Chloride omega-Chloroacetophenone alpha-Chloroacetophenone Phenyl Chloromethyl Ketone Tear Gas Chloromethyl Phenyl Ketone Chemical Formula CeHjCOCHjCl. 

Chlorobenzene Producers Association (CPA), 270 p-Chlorobenzotrichloride, 39 Chlorobenzotrifluorides, 39 Chlorobromomethane, 39 Chlorodifluorobromomethane, 39 Chlorodifluoroethane, 39 Chlorodifluoromethane, 39 Chlorodiphenyl, 39 Chloroethanol, 39 2-Chloroethyl vinyl ether, 39 Chlorofluorocarbons, 39 Chloroform, 40 Chloromethyl anilines, 40 Chloromethyl ether, 40 Chloromethyl methyl ether, 40 2-(4-Chloro-2-methylphenoxy) propionic acid, 40 Chloromethyl phenyl isocyanate, 40... 

Also, the observed highly regioselective course in the SnFI substitutions in 2-R-3-nitro-l, 8-naphthyridines (R = FI, OFI, Cl, NFI2, OEt) with the anion of chloromethyl phenyl sulfone was explained by MNDO quantum-chemical calculations showing that, like in the aminations, the interaction of FIOMO of the nucleophile with LUMO of the nitronaphthyridines controls the regioselectivity (91JFIC1075). 

The reaction of 3-methoxy-1,2,4-triazine 1-oxide 20 with the carbanion generated from chloromethyl phenyl sulfone proceeds as the vicarious nucleophilic substitution (VNS) of hydrogen (Scheme 1, path B) via addition of the carbanion at position 5 of the heterocycle. Following base-induced elimination of HCl and protonation, 3-methoxy-5-phenylsulfonyl-1,2,4-triazine 4-oxides 65 result (88LA627). 

At the same time, the reaction of 1,2,4-triazine 4-oxides 55 with the anion of chloromethyl phenyl sulfone affords 5-(l-chloro-l-phenylmethyl)-l,2,4-triazines 66. In this case, autoaromatization of the a -adducts proceeds by the deoxygenative... 

Chloro-3-hydroxybutyronitrile, byproduct in preparation of 3-hydroxyglu taronitrile, 46, 49 3-hydroxyglutaronitrile from, 46, 49 1-Chloro-l-methylcyclohexane as precursor of 1-methylcyclohexane-carboxylic acid, 46, 73 Chloromethyl phenyl ether, 47,... 

Addition of BuLi to a 0.3 M solution of chloromethyl phenyl sulfoxide in THF at — 78 "C yields an immediate bright-yellow solution containing the lithio derivative which is stable for at least 2 h at —78 rC. Decomposition occurs rapidly above —20 C with the solution becoming turbid and the color changing to dark brown. Reaction of the lithiated solution of chloromethyl phenyl sulfoxide with cyclohexanone, acetone, or ben/ophenone for 10 min at —78 °C followed by 30 min at —20 rC yields one diastereomeT in 79, 75 and 68 % yields, respectively, after hydrolysis of the corresponding adducts. 

E. Reduction of Halomethyl Phenyl Sulfones and Chloromethyl Phenyl... 

Nitro-, 4-nitro-, 7-nitro-, 5,7-dinitro-, and 6,8-dinitroquinoline react with the carbanion of chloromethyl phenyl sulfone to give products of substitution of hydrogen at positions 4 3 8 6,8 and 5,7 respectively <96LA641>. The base-induced reaction of benzoyl chloride salts of quinoline iV-oxides with carbonitriles to give 2-quinolyldiacylamines as the main products has been reported <96TL(37)69>. 

Reaction of the carbanion of chloromethyl phenyl sulphoxide 409 with carbonyl compounds yields the corresponding 0-hydroxy adducts 410 in 68-79% yield. Each of these compounds appears to be a single isomer (equation 242). Treatment of adducts 410 with dilute potassium hydroxide in methanol at room temperature gives the epoxy sulphoxides 411 (equation 243). The ease of this intramolecular displacement of chloride ion contrasts with a great difficulty in displacing chloride ion from chloromethyl phenyl sulphoxide by external nucleophiles . When chloromethyl methyl sulphoxide 412 is reacted with unsymmetrical ketones in the presence of potassium tcrt-butoxide in tert-butanol oxiranes are directly formed as a mixture of diastereoisomers (equation 244). a-Sulphinyl epoxides 413 rearrange to a-sulphinyl aldehydes 414 or ketones, which can be transformed by elimination of sulphenic acid into a, 8-unsaturated aldehydes or ketones (equation 245). The lithium salts (410a) of a-chloro-/ -hydroxyalkyl... 

Fig. 16. Chiral 4th-generation dendrimers from para- or meto-(chloromethyl)-phenyl substituted acetonides and a 1,3,5-benzenetricarboxylic acid center piece [72]... 

Control of the regioselectivity of VNS is important. It is governed by three major factors the structure of the nitroarene the nature of the nucleophile, and the reaction conditions, especially solvent and base. The different effect of methoxy and hydroxy groups is interesting the reaction of l-methoxy-2,4-dinitrobenzene with chloromethyl phenyl sulfone proceeds in... 

Synonyms AI3-52322 BRN 0507950 CAP CAP Caswell No. 179C CCRIS 2370 Chemical mace 1-Chloroacetophenone 2-Chloroacetophenone Q-Chloroacetophenone Chloromethyl phenyl ketone 2-Chloro-l-phenylethanone CN EINECS 208-531-1 EPA pesticide chemical code 018001 Mace NC1-C55107 NSC 41666 Phenacyl chloride Phenyl chloromethyl ketone Tear gas UN 1697. 

Chloromethyl) oxhane, see Epichlorohydrin 2-(Chloromethyl)oxirane, see Epichlorohydrin 4-Chloro-3-methylphenol, see p-Chloro-ro-cresol p-Chloro-3-methylphenol, see p-Chloro-ro-cresol Chloromethyl phenyl ketone, see a-Chloroacetophenone p-Chloronaphthalene, see 2-Chloronaphthalene 4-Chloronitrobenzene, see p-Chloronitrobenzene l-Chloro-4-nitrobenzene, see p-Chloronitrobenzene 4-Chloro-l-nitrobenzene, seep-Chloronitrobenzene p-Chloro-1-nitrobenzene, see p-Chloronitrobenzene Chloronitroform, see Chloropicrin Chloronitropropane, see 1-Chloro-l-nitropropane Chlorophen, see Pentachlorophenol... 

Fig. 11 Wet thickness (H) of PAAm in water as a function of the PAAm graft density for samples prepared by surface-initiated ATRP on substrates with gradient of initiator density. The initiator was immobilized by the vapor-diffusion method using mixtures of l-trichlorosilyl-2-(fn/p-chloromethyl phenyl)ethan n-octyl trichlorosilane (w/w) 1 1 (squares), 1 2 (circles), and 1 5 (triangles). The inset shows a cartoon illustrating the polymer behavior. Reproduced with permission from [134] (Copyright 2003 American Chemical Society)...

In 1993, Satoh and coworkers reported the preparation of lithium- and magnesium-aUtylidene carbenoids from 1-chlorovinyl phenyl sulfoxides by sulfoxide-metal exchange reaction at low temperature (Scheme 6). 1-Chlorovinyl phenyl sulfoxide (128) is easily synthesized from the corresponding aldehyde and chloromethyl phenyl sulfoxide in high yield. Sulfoxide 128 was treated with f-BuLi in THF at —78 °C to give the terminal alkyne 131. Obviously, the intermediate of this reaction was the alkylidene carbenoid 129. 

Trifluoromethyl iodide is a poor substrate for SN2 reactions [28], The increased donativity of the methylene carbon as rendered by the fluorine atoms is reflected in its reluctance to enter a bonding relationship with a nucleophile. Similar reactivity patterns are known for chloromethyl phenyl sulfone [28] and chloromethyltrimethyl-silane. In these latter compounds the reactive center is directly linked to an acceptor group. 

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