W-Chloroacetophenone

Holland, P. and White, R.G. The cutaneous reactions produced by o-chlorobenzylidene malononitrile and w-chloroacetophenone when applied directly to the skin of human subjects. Br. J. Dermatol.86 150-154, 1972. 

Grignard reagents are not enough basic to abstract a vinylic hydrogen, nor do they participate in halogen metal exchange. As shown, they instead substitute the reactive chlorine atom in a-chloroenamines. More recent work has shown that 87 a, R = Me can be obtained from (w-chloroacetophenone and tris-dimethylamino) arsine in 86%... 

Diphenylpyrazine (1, R = R = Hi, R = R = H) was the second pyrazine synthesized, and it was prepared by Staedel and Riigheimer (10) in 1876 by the action of ammonia on w-chloroacetophenone and was named isoindol. These authors postulated the first structure for a pyrazine as an inner anhydride (2) of an amino ketone. 

CHLOROACETO PHENONE or 2-CHLOROACETOPHENONE or a-CHLORO-ACETOPHENONE or w-CHLOROACETOPHENONE (532-27-4) Combustible solid (flash point 244°F/118°C cc). Reacts with water, forming hydrogen chloride fumes. Reacts with aldehydes, nitric acid, perchloric acid. Reacts slowly with metals, causing mild corrosion. 

Catechol is an intermediate for the synthesis of racemic adrenaline which, although quite medicinally active, can be resolved (ref. 36) in 71% yield to afford the more active R(-) enantiomer, the natural form, which can also be derived quantitatively by asymmetric reduction (ref. 37) of the synthetic precursor, adrenalone as the hydrochloride by catalytic hydrogenation in methanol containing the rhodium complex of (R)-o[(S)-1 ,2-bis(diphenylphosphine)ferrocenyl]ethyl alcohol. Adrenalone is obtained by the acylation of catechol with chloroacetyl chloride to afford 3,4-dihydroxy-w-chloroacetophenone followed by reaction with methylamine. 

For the purposes of this chapter, "chemical warfare agent" (CWA) is used as a fairly comprehensive term to refer to a diverse group of toxicants commonly discussed within the context of chemical incapacitation for crowd control during riots or death or incapacitation associated with military use or terrorism. The lachrymatory and irritant riot control agents include a-chlorbenzylidene malonitrile (CS), dibenz b,f)-VA oxazepine (CR), w-chloroacetophenone (CN), and oleoresin of capsicum (OC pepper spray) (Salem et al., 2008a). The CWAs... 

A. (o-Bromo-p-chloroacetophenone oxime. A 500-mL, four-necked, round-bottomed flask equipped with a dropping funnel (closed with a giass stopper), mechanicai stirrer, drying tube (calcium chioride, CaCij), and a thermometer is charged with p-chloroacetophenone (38.6 g, 0.25 moi), glacial acetic add (220 mL) and aqueous hydrobromic acid (HBr) [1 mL, 48 % (w/w). Note 1]. The flask is immersed in a water bath (15°C, Note 2) and bromine (40.0 g, 0.25 mol) is added from the dropping funnei at such a... 

A three-necked, round-bottomed flask with Claisen head may be used instead. p-Chloroacetophenone (97%), hydroxylamine hydrochloride (purum p.a. >98%), potassium 0-ethyl xanthogenate (>98%), bromine (puriss. p.a., >99.5%), and hydrobromic add [puriss. 48% (w/w)] were obtained from Ruka Chemika and used as... 

Ballantyne, B. and Swanston, D.W. The comparative acute mammalian toxicology of 1-chloroacetophenone (CN) and 2-chlorobenzylldene malononltrlle (CS). Arch. Toxicol. 40 75-95, 1978. 

Ballartyne, B., Gazzard, M.J., Swanston, D.W., and Williams, P. The comparative ophthalmic toxicology of 1-chloroacetophenone... 

Chung, C.W., Giles, A.L. (1972). Sensitization of guinea pigs to alpha-chloroacetophenone (CN) and ortho-chlorobenzylidene malononitrile (CS), tear gas chemicals. J. Immunol. 109 284-93. 

Hydroxyacetophenone Azide (called Azido-4-oxy-acetophenone in Ger) HOC6H4COCH2N3, mw 177.16, N 23.72% yel leaflets (from w) mp 136°, sol in the usual solvents except benzene decomposes in boiling w Prepd by heating 4-hydroxy-chloroacetophenone with Na Azide in ale. No explosive props are mentioned Ref Beil 8 [87]... 

By adding it in small quantities to a mixture of fuming nitric acid and sulphuric acid, shaking after each addition, it is converted into benzoic acid and w-nitro-a-chloroacetophenone ... 

Drying w-bromo-p-chloroacetophenone oxime was carried out in the dark since otherwise this material turns pink in light. Wrapping the flask with aluminum foil provides adequate light protection for this purpose. 

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