4 -chloroacetophenone

Sargent EV, Kirk GD, Hite M Hazard evaluation of monochloroacetone. Am Ind Hyg Assoc 747 375-378, 1986 

Anonymous Monochloraceton. Berater-gremium fuer umweltrelevante Altstoffe (BUA) Vol 226, 71pp, 2001 

Synonyms 2-Chloro-l-phenylethanone phenacyl chloride phenyl chloromethyl ketone tear gas chemical Mace 

Chemical warfare agent (CN) principal constituent in riot control agent Mace in tear gas formulations for personal protection devices 

Sporadic cases of dermatitis due to primary irritation by a-chloroacetophenone have been reported. Allergic contact dermatitis to this substance in chemical Mace has been documented by patch test evaluation, and it is said to be a potent skin sensitizer.  

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Chloroaeetophenone oxime was prepared by a modification of the method described by Shriner, Fuson, and Curtin.5 A mixture of 100 g. (0.65 mole) of reagent-grade 4-chloroacetophenone, 300 ml. of water, 200 ml. of aqueous 10% sodium hydroxide, 50g. (0.72 mole) of hydroxyl-amine hydrochloride, and 500 ml. of ethanol is heated at reflux in a 2-1. round-bottomed flask for 2 hours. The crystals that separate on cooling in an ice bath are recovered by filtration and air dried. The product is added to approximately 1 1. of hexane, and the mixture is... 

CSH7CIO 2142-68-9) see Clofedanol Clorprenaline Fenclofenac Tulobuterol Zotepine 4 -chloroacetophenone... 

Dihydropyrrolizine 219, a precursor of ML 300, was efficiently obtained in a one-step cyclization between cyclic imine 218 and tu-bromo-4-chloroacetophenone in the presence of NaHC03 (Scheme 53) <2003W0018583>. 

Incidents involving reactions with either ammonia or organic amines (sometimes only in catalytic proportions) may be found under the entries Benzenediazonium-2-carboxylate, Aniline, or Isocyanides, 2659 4-Chloroacetophenone, Dimethylamine, 2929... 

The reduction of a dinitro ketone to an azo ketone is best achieved with glucose. 2,2 -Dinitrobenzophenone treated with glucose in methanolic sodium hydroxide at 60° afforded 82% of dibenzo[c,f [i 2]diazepin-l 1-one whereas lithium aluminum hydride yielded 24% of bis(o-nitrophenyl)methanol [575], Conversion of aromatic nitro ketones with a nitro group in the ring into amino ketones has been achieved by means of stannous chloride, which reduced 4-chloro-3-nitroacetophenone to 3-amino-4-chloroacetophenone in 91% yield [178]. A more dependable reagent for this purpose proved to be iron which, in acidic medium, reduced m-nitroacetophenone to m-aminoacetophenone in 80% yield and o-nitrobenzophenone to o-aminobenzophenone in 89% yield (stannous chloride was unsuccessful in the latter case) [903]. Iron has also been used for the reduction of o-nitrochalcone, 3-(o-nitrophenyl)-l-phenyl-2-propen-l-one, to 3-(o-aminophenyl)-l-phenyl-2-propen-l-one in 80% yield [555]. 

Clemastine Clemastine, 2-[2-[l-(4-chlorophenyl)-l-phenylethoxy]ethyl]-l-methylpyrroli-dine (16.1.4), is synthesized by reacting l-(4-chlorophenyl)-l-phenylethanol (16.1.3) with 2-(2-chlorethyl)-2-methylpyrrolidine using sodium amide as a base. The starting l-(4-chlorophenyl)-l-phenylethanol (16.1.3) is synthesized either by reacting 4-chloroben-zophenone with methylmagnesium chloride, or by reacting 4-chloroacetophenone with phenylmagnesium bromide [6-8]. 

The reduction of 4-chloroacetophenone mediated by L. kefir stopped at 46% conversion owing to the reactant and/or the product being toxic to the cell membrane [100]. The addition of TBME (20%, v/v) made the situation worse because... 

The telluronium salt 142 obtained from telluroisochromane and o -bromo-4-chloroacetophenone upon treatment with silver o-bromcamphor-sulfonate produced two diastereomers which were separated by crystallization from ethanol and then converted to their enantiomeric picrates. Racemization due to inversion of their pyramidal configuration at the tricoordinate tellurium center occurs slowly and was accomplished at room temperature over 20 days (45JCS37). 

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