A Chloroacetophenone

A solution of 2,3-dibromo-5-methoxyaniline (32 g, 0.17 mol) in CHjClj (300 ml) was stirred and cooled in an icc bath. Boron trichloride (1 M in CH2CI2, 180 ml, 0.18 mol), chloroacetonitrile (14.3 g, 0.19 mol) and TiC (1 M in CH CIj, 190ml, 0.19 mol) were added. The resulting mixture was refluxed for 1.5 h. The solution was cooled to room temperature and poured carefully on to a mixture of icc and 20% aq. HCl (700 ml). The organic layer was separated and the CH Clj removed by distillation. The residue was heated to 90°C on a water bath for 30 min. The solution was cooled and the solid collected by filtration. It was partitioned between ether (1.41) and 1 N NaOH (500 ml). The ether layer was washed with brine, dried over Na2S04 and evaporated. The residue was recrystallized from ethanol to give 2-amino-3,4-dibromo-6-methoxy-a-chloroacetophenone (55 g) in 90% yield. 

Stoddard solvent VM P naphtha Phenacyl chloride, see a-Chloroacetophenone... 

Chloro-1 -nitropropane Chloroacetaldehyde a-Chloroacetophenone Chlorobenzene (monochlorobenzene) o-Chlorobenzylidine malononitrile Chlorobromomethane Chlorodiphenyl (42% chlorine) Chlorodiphenyl (54% chlorine) 2-Chloroethanol (ethylene chlorohydrin) Chloroform... 

C-07100,see2,4,5-T C-07101, see 2,4,5-Trichlorophenol C-07328, see Isoamyl alcohol C-07557, see TCDD C-08374, see Dodecane C-08380, see 2-Heptanone C-11043, see Methoxychlor C-11088, see 2,6-Dinitrotoluene C-11142, see Phenanthrene C-11160, see Thiram C-11233, see Dimethylphthalate C-14098, see 2-Methylnaphthalene C-10998, see 4-Aminobiphenyl C-11249, see Cyclohexane C-2292-52A, see Carbofuran CAF, see a-Chloroacetophenone Calmathion, see Malathion 2-Camphanone, see Camphor Camphechlor, see Toxaphene Camphochlor, see Toxaphene Camphoclor, see Toxaphene DL-Camphor, see Camphor Camphor-natural, see Camphor Camphor-synthetic, see Camphor Camphor tar, see Naphthalene Candaseptic, see p-Chloro-m-cresol Canogard, see Dichlorvos CAP, see a-Chloroacetophenone Caprolin, see Carbaryl... 

CF 2, see 1,1,1-Trichloroethane CFC 11, see Trichlorofluoromethane CFC 21, see Dichlorofluoromethane CFC 112, see 1,2-Difluorotetrachloroethane CFC 112a, see 1,1-Difluorotetrachloroethane CFC 113, see 1,1,2-Trichlorotrifluoroethane Chelen, see Chloroethane Chemform, see Methoxychlor Chemathion, see Malathion Chemical 109, see ANTU Chemical mace, see a-Chloroacetophenone Chemox PE, see 2,4-Dinitrophenol Chempenta, see Pentachlorophenol Chemphene, see Toxaphene Chemrat, see Pindone Chemsect DNOC, see 4,6-Dinitro-ocresol Chemtol, see Pentachlorophenol Chevron acetone, see Acetone Chimec NR, see 2-Bntoxyethanol Chinone, see / Qninone Chinnfnr, see Carbofuran Chipco thiram 75, see Thiram Chipco turf herbicide "D", see 2,4-D Chladone 11, see Trichlorofluoromethane Chlon, see Pentachlorophenol Chlorallylene, see Allyl chloride Chloran, see Lindane 4-Chloraniline, see 4-Chloroaniline p-Chloraniline, see 4-Chloroaniline Chlorbenzene, see Chlorobenzene Chlorbenzol, see Chlorobenzene p-Chlor-ro-cresol, see p-Chloro-ro-cresol Chlordantoin, see Amyl acetate Chlordan, see Chlordane... 

Chloroacetophenone, see a-Chloroacetophenone Q-Chloroacetophenone, see a-Chloroacetophenone cfs-3-Chloroallyl chloride, see cfs-l,2-Dichloropropylene frarrs-3-Chloroallyl chloride, see frarrs-l,2-Dichloro-... 

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... 

Chloro-l-phenylethanone, see a-Chloroacetophenone 4-Chlorophenyl ether, see 4-Chlorophenyl phenyl ether p-Chlorophenyl ether, see 4-Chlorophenyl phenyl ether Chlorophenylmethane, see Benzyl chloride [(2-Chlorophenyl)methylene]propanedinitrile, see o-... 

Phenyl chloromethyl ketone, see a-Chloroacetophenone 1,4-Phenylenediamine, see p-Phenylenediamine /72-Phenylene dichloride, see 1,2-Dichlorobenzene... 

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. ... 

The 2003 ACGIH threshold limit value-time-weighted average (TLV-TWA) for a-chloroacetophenone is 0.05 ppm (0.32 mg/m ). 

Toxicology. a-Chloroacetophenone is a potent lacrimating agent and an irritant of mucous membranes it causes dermatitis of both primary irritation and sensitization type. 

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