Chloro acetophenone

These efforts began with directed lithiation [53] of commercially available 4-methoxybenzaldehyde dimethyl acetal (117, Scheme 1.12), followed by quenching with amide 118 to produce chloro acetophenone 119 (52 %). Conversion... 

The reaction of triphenylphosphine with 2-acylamino-2-(chloro)acetophenones gives the salts (113), which may be cyclized to the oxazolylphosphonium salts (114).113 Similarly, the halogenocarboxamides (115) react readily with triphenylphosphine to give the enamide phosphonium salts (116), which on treatment with primary or secondary amines give the salts (117).114... 

Helland, D.R. A cllnlcopathologic study of the effects of riot control agents on monkeys. I.Dlphenylaminochloroarslne-chloro-acetophenone (DM-CN) grenade. U.S. Army Medical Research Laboratory, Edgewood Arsenal, Md. Technical Report EATR 4068. 1967. 

The following couples were tested p-chlorobenzonitrile/p-chloro-acetophenone, p-chloroacetophenone/p-chlorodiphenyl, p-chlorodiphenyl /chlorobenzene, p-chlorodiphenyl/p-chlorofluorobenzene, chlorobenzene /p-chlorotoluene, chlorobenzene/p-chloroanisole, p-chloroacetophenone/ methyl ester of m-chlorobenzoic acid, chlorobenzene/m-chlorotoluene, p-chlorodiphenylether/p-chlorotoluene, m-chlorodiphenylether/chloroben-zene, m-chlorodiphenylether/p-chlorotoluene, chlorobenzene/methyl ester of m-chlorobenzoic acid, chlorobenzene/p-bromoanisole, p-bromoaceto-phenone / p-chlorobenzonitrile, p-bromobenzonitrile / p-chloroacetophe-none, bromobenzene/p-chlorodiphenyl, m-bromotoluene/chlorobenzene, and p-chlorodiphenyl/p-bromotoluene. 

To obtain more information on the nature of the quasiphosphonium intermediates involved in these systems we have studied the reactions gf sterically hindered neopentyl esters by means of 1P nmr spectroscopy. Trineopentyl phosphite and a-bromoacetophenone gave rise to a peak at +41 ppm due to the ketophosphonium intermediate 3 (R = Me.CCH, R = Ph X = Br ) within half an hour of mixingJthe reactants in acetone-dfi at 27 °C ( p nmr shifts are relative to 85% H-PO. down-field positive). Peaks due to the ketophospnonate 4 +19 ppm and the vinyl phosphate 7 (-7 ppm) were also observed (compound 4 and 7 have satisfactory elemental analysis and spectroscopic data ). The concentration of the intermediate reached a maximum after about two hours when it was precipitated from acetone solution by the addition of anhydrous ether to give white crystals of trineopentyloxy (phenacyl)phosphonium bromide, identified by elemental analysis and nmr spectroscopy ( XP 6+41, in CDCl ). When redissolved in acetone-dg, deuterochloroform, acetic acid, or acetic acid-acetone mixtures, the intermediate decomposed to yield keto-phosphonate 4 but none of the vinyl phosphate 6 (Perkow product). Nor was the course of reaction affected by the addition of chloride ion or of a-chloro-acetophenone in acetonitrile. 

Fluoro 6 chloro acetophenone see 2 Fluoro phenacyl chloride 4 Fluoro 2 chloro benzophenone see 2 Chloro phenyl 4 fluoro phenyl ketone Fluoro dichloro methyl sulfenyl chloride dichlorofluanid... 

It is well known that deoxycholic acid 1 forms inclusion complexes with a number of guest molecules. The crystalline inclusion complexes 87a-c l were obtained from solutions of deoxycholic acid 1 with acetophenone 87a, ra-chloro-acetophenone 87b, or / -fluoroacetophenone 87c in methanol. The host guest molar ratios are 5 2, 3 1, and 8 3, respectively. The guest molecules are... 

SYNS CAP CAP CHExMICALMACE CHLORACETOPHENONE co-CHLOROACETOPHEN-ONE 1-CHLOROACETOPHENONE CHLORO-ACETOPHENONE, Uquid or soUd (DOT) CHLORO-METHYL PHENAX KETONE 2-CHLORO-l-PHENYL-ETHANONE CN ETHANONE, 2-CHLORO-l-PHENYL- MACE (lachr> mator) NCI-C55107 PHENACYL CHLORIDE PHENYLCHLORO-METHYLKETONE... 

The method is especially valuable for the preparation of certain substituted acetophenones, namely, o- and p-nitroacetophenone and o-chloro-acetophenone. Methods involving Grignard, Friedel-Crafts, or nitration reactions are apparently not applicable for the preparation of these nitro compounds, and the Friedel-Crafts reaction is not applicable to the preparation of o-chloroacetophenone. Although the acetoacetic ester synthesis has been used for the preparation of these and other substituted acetophenones, it may be complicated by O-acylation and also by cleavage at either acyl group (cf. method 212). 

DM is considered less effective as a riot control or incapacitating agent than CS and CN (chloro-acetophenone), and it has been conjectured that there are greater differences in susceptibility among people to DM than to the other agents. DM, like CS, is considered to be a cholinesterase inhibitor, which may be responsible for its lacrimatory effect. DM also has a direct effect on gastric activity, but the evidence suggests that the lethal effect is respiratory related. 

Wills has described new catalysts containing a N-P=0 structural unit such as 76 and 77 (Fig. 7) [117,118,119]. The highest selectivity (92% ee) using 77 was obtained when 10 mol % of the catalyst was used in the reduction of co-chloro-acetophenone in toluene at 110 °C, whereas the reduction of acetophenone proceeded with 82% ee under the same conditions [120]. 

Chloro- acetophenone Phenacyl Chloride Omega-Chloro- acetophenone Alpha-Chloro- acetophenone Phenyl Chloromethyl Ketone Tear Gas... 

Figure 2. Temperature dependence for Mechanisms HI and TV. (E2 - EA) = 4.4 kcal. E = 1.4 kcal. EA = (1) 12 (2) 8 (3) 6 (4) 4 (5) 0 kcal. Circles represent data for 3-chloro acetophenone solid line through the data for the parameters E2 = 17.8 kcal., EA = 13.4 kcal., Ej = 1.4 kcal.

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. 

The mixture of 2.7 g o-amino acetophenone (0.02 mol) and 3.08 g a-chloro-acetophenone (0.02 mol) in 50 mL anhydrous DMF was heated in an oil bath (80-90°C) for 16 h. The reaction mixture was then poured over 1500 mL ice water, and the crystalline 2-benzoyl-3-methyl-indole was isolated by filtfation and was further purified by recrystaUization Irom methanol, giving 69% yield, m.p., 138-139°C. 

Method Q is based on Pd2(dba)3 / ArPCy2-type phosphine 237 catalysis and provides a convenient high-yielding SM procedure with aryl chlorides under reasonably mild reaction conditions (refluxing toluene, 105-110 °C) [11,33]. For instance, 2-chloro acetophenone (289) was coupled with 4-tolylboronic acid (271) to give 290 in 83% yield [33], respectively. Scheme 27. The method is not sensitive to the steric hindrances in both counterparts. 

Chinese reports allege that the Japanese employed gas in China from 18 July 1937 to 8 May 1945. They also allege that the Japanese used diphenylchloroarsine (DA), diphenylcyanoarsine (DC), chloro-acetophenone (CN), chloropicrin, hydrogen cyanide, phosgene, mustard and lewisite. By the end of 1941, Chinese sources claim that over 1000 gas attacks had been delivered. Although the statistics are not necessarily reliable (since there are discrepancies between the various reports), the data from the Chinese Gas Defence Department reveals an interesting pattern of usage ... 

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