4- Chlorobenzyl cyanide

Chlorobenzyl cyanide Sodium hydride Hydrochloric acid Thionyl chloride Diethylene glycoldimethyl... 

A solution of 4-chlorobenzyl cyanide and 1,3-dibromopropane in dry dimethylsulfoxide was added dropwise under nitrogen to a stirred mixture of sodium hydride dispersed in mineral oil and dimethylsulfoxide at a temperature in the range 30° to 35°C. The mixture was stirred at room temperature for 2 h and propan-2-ol and then water were added dropwise. The mixture was filtered through a diatomaceous earth sold under the Registered Trade Mark CELITE and the solid residue washed with ether. The ether layer was separated, washed with water, dried and evaporated. l-(4-Chlorophenyl)-l-cyclobutanecarbonitrile was isolated by distillation. 

C3H5S 870-23-5) see Altizide allyl(l-methyl-2-pentynyl)malonic acid diethyl ester (C16H24O4 101448-52-6) see Methohexital 4-allyloxy-3-chlorobenzaldehyde (CigH Cl02, 58236-91-2) see Alclofenac 4-allyloxy-3-chlorobenzyl chloride (C Hi()Cl20 20788-43-6) see Alclofenac 4-allyloxy-3-chlorobenzyl cyanide (C, H C1N0 20788-44-7) see Alclofenac... 

C-Methylation of side chain of p-chlorobenzyl cyanide p-chlorobenzyl cyanide, isopropyl halide... 

Amino-3-pyridinecarbonitrile (34) with ra-chlorobenzyl cyanide gave 3-m-chlorophenyl-1,8 naphthyridin-2-amine (35) (neat reactants, trace KOH/ H20, microwave 98%) 77 the same substrate (34) with methyl cyanoacetate... 

A study of those compounds in which the CN-group is in the side chain containing the halogen atom has indicated that chlorobenzyl cyanide, and bromobenzyl cyanide to an even greater degree, have an increased lachrymatory power. These compounds are described in the chapter on Cyanogen Compounds (see p. 196). 

Various other compounds containing the CN— radicle were studied towards the end of the war and since that period. Of these, chlorobenzyl cyanide, bromobenzyl cyanide, diphenyl cyanoarsine, phenarsazine cyanide, etc., were used to a considerable extent as war gases. Recently cyanogen fluoride has also been prepared and studied. It is a colourless gas with powerful lachrymatory properties. 

Benzyl cyanide p-chlorobenzyl Benzyl chloride, sodium cyanide p-chlorobenzyl... 

In mammalian species, CS rapidly hydrolyzes to form 2-chlorobenzaldehyde and malononitrile (Leadbeater, 1973 Paradowski, 1979 Rietveld et a/., 1986). The malononitrile intermediate is further metabolized from two cyanide moieties, which are converted to thiocyanate (Cucinell et al, 1971). The aldehyde intermediate undergoes oxidation to 2-chlorobenzoic acid or reduction to 2-chlorobenzyl alcohol. These metabolites are conjugated and excreted in the urine. 

CS is absorbed very rapidly from the respiratory tract, and the half-lives of CS and its principal metabolic products are extremely short. The disappearance of CS follows first-order kinetics and spontaneously hydrolyses to malononitrile, which is transformed to cyanide in animal tissues. Metabol-ically, CS undergoes conversion to 2-chlorobenzyl malononitrile (CSH2), 2-chlorobenzaldehyde (oCB), 2-chlorohippuric acid, and thiocyanate. CS and its metabolites can be detected in the blood after inhalation exposure, but only after large doses. Following inhalation exposure of CS in rodent and nonrodent species, CS and two of its metabolites, 2-chlorobenzaldehyde and 2-chlorobenzyl malononitrile, were detected in the blood. In another study, human uptake by the respiratory tract, only 2-chlorobenzyl malononitrile was detected in trace amounts in the blood. CS and 2-chlorobenzaldehyde were not detected, even after high doses of CS of up to 90 mg min m. This finding is consistent with the... 

Table 13 The incoming group nC/14C carbon and secondary a-deuterium KIEs for the SN2 reactions between meta-chlorobenzyl-para-substituted benzenesulfonates and cyanide ion in 0.5% aqueous acetonitrile at 0°C...

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