Synthesis of chloroacetophenone

Preparation of chloroacetophenone

Chloroacetophenone is prepared by the action of chlorine on acetophenone.

Preparation of chloroacetophenone

Preparation of chloroacetophenone

To the round bottom flask fitted with a reflux condenser, stirrer and gas inlet tube a solution of 20 g acetophenone in 100 g acetic acid is placed. The reaction mixture is weighed and with vigorous stirring a rapid stream of chlorine is passed through the solution. If the reaction is very rapid cooling with ice-water bath may be applied. Chlorine is passed until the necessary amount of gas has been absorbed and reaction mixture is kept at room temperature until the liquid becomes colorless. Finally the reaction mixture is poured into ice-water where the products separates as an oily liquid which rapidly solidifies. The crystals are filtered and washed with distilled water and crystallized from dilute ethyl alcoholChloroacetophenone forms colorless or slightly yellowish crystals which melt at 58-59° C and boil at 244-245° C.

The war gases chemistry and analysis, by M. Sartory, 156, 1939.

IUPAC Name

2-chloro-1-phenylethanone

InChI

InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

InChI Key

IMACFCSSMIZSPP-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)CCl

MeSH Synonyms

2 Chloro 1 phenylethanone, 2 Chloroacetophenone, 2-Chloro-1-phenylethanone, 2-Chloroacetophenone, 3′-Chloroacetophenone, alpha Chloroacetophenone, alpha-Chloroacetophenone, Chloracetophenone, Chloroacetophenone, Mace, omega Chloroacetophenone, omega-Chloroacetophenone

Depositor-Supplied Synonyms

2-CHLOROACETOPHENONE, Phenacyl chloride, 2-Chloro-1-phenylethanone, 532-27-4, Tear Gas, omega-Chloroacetophenone, CHLOROACETOPHENONE, alpha-Chloroacetophenone, Mace (lacrimator), 1-Chloroacetophenone, Mace, Acetophenone, 2-chloro-, Chloromethyl phenyl ketone, Ethanone, 2-chloro-1-phenyl-, Phenacylchloride, Chemical mace, CN (lacrimator), Phenyl chloromethyl ketone, NCI-C55107, 2-Chloroacetophenone (CN), 2-Chloro-1-phenyl-ethanone, a-Chloroacetophenone, 2-Chloro-1-phenylethan-1-one, Phenylchloromethylketone, Caswell No. 179C, NSC 41666, .alpha.-Chloroacetophenone, .alpha.-Phenacyl chloride, .omega.-Chloroacetophenone, UNII-88B5039IQG, CCRIS 2370, HSDB 972, CN, IMACFCSSMIZSPP-UHFFFAOYSA-N, EINECS 208-531-1, UN1697, EPA Pesticide Chemical Code 018001, BRN 0507950, AI3-52322, DSSTox_CID_293, DSSTox_RID_75493, DSSTox_GSID_20293, Chloroacetophenone (CN), solid [UN1697] [Poison], Chloracetophenone, CAS-532-27-4, Chloroacetyl benzene, Benzoylmethyl chloride, 2-chloro acetophenone, 2-chloro-acetophenone, PubChem3264, 2-Chloroacetonephenone, alpha-Phenacyl chloride, Chloroacetophenone, 2-, AC1L1VVT, W-CHLOROACETOPHENONE, WLN: G1VR, Phenyl chloromethy l ketone, AC1Q3T9R, AC1Q3T9S, AC1Q5F5I, SCHEMBL55444, C19686_ALDRICH, BETA-CHLOROACETOPHENONE, KSC103C9B, (2-Chloro-1-oxoethyl)benzene, 1-Phenyl-2-chloro-1-ethanone, CHEMBL105712, Chloroacetophenone (CN), solid, GTPL6285, PARAGOS 530514, Chloroacetophenone (CN), liquid, 77460_FLUKA, ATTERCOP-CHM AT113381, MolPort-000-913-150, OTAVA-BB 1366928, 88B5039IQG, LABOTEST-BB LTBB002807, NSC41666, STR01480, Halomethyl Phenyl Ketone deriv. 21, Tox21_202075, Tox21_300045, ANW-64249, LABOTEST-BB LT03333320, LS-192, NSC-41666, SBB058832, ZINC01673519, AKOS000200777, AS01163, MCULE-1687900460, RP17374, RTC-063631, UN 1697, NCGC00091207-01, NCGC00091207-02, NCGC00091207-03, NCGC00091207-04, NCGC00091207-05, NCGC00254035-01, NCGC00259624-01, AK-48314, AN-45636, CJ-27265, KB-22794, DB-013352, TC-063631, FT-0649549, EN300-18309, 4636-EP2269992A1, 4636-EP2269994A1, 4636-EP2270001A1, 4636-EP2270004A1, 4636-EP2270014A1, 4636-EP2270018A1, 4636-EP2272510A1, 4636-EP2272517A1, 4636-EP2272825A2, 4636-EP2272837A1, 4636-EP2272848A1, 4636-EP2272972A1, 4636-EP2272973A1, 4636-EP2274983A1, 4636-EP2275105A1, 4636-EP2275395A2, 4636-EP2275416A1, 4636-EP2275422A1, 4636-EP2277848A1, 4636-EP2277858A1, 4636-EP2277862A2, 4636-EP2277865A1, 4636-EP2277866A1, 4636-EP2277869A1, 4636-EP2277870A1, 4636-EP2277871A1, 4636-EP2277872A1, 4636-EP2277876A1, 4636-EP2277877A1, 4636-EP2277882A1, 4636-EP2277898A2, 4636-EP2280005A1, 4636-EP2280008A2, 4636-EP2280282A1, 4636-EP2281810A1, 4636-EP2281815A1, 4636-EP2281823A2, 4636-EP2281861A2, 4636-EP2284148A1, 4636-EP2284149A1, 4636-EP2284157A1, 4636-EP2284178A2, 4636-EP2284179A2, 4636-EP2286915A2, 4636-EP2287154A1, 4636-EP2287165A2, 4636-EP2287166A2, 4636-EP2287167A1, 4636-EP2289509A2, 4636-EP2289868A1, 4636-EP2289871A1, 4636-EP2289876A1, 4636-EP2289884A1, 4636-EP2289891A2, 4636-EP2292088A1, 4636-EP2292227A2, 4636-EP2292234A1, 4636-EP2292595A1, 4636-EP2292607A2, 4636-EP2292608A1, 4636-EP2292614A1, 4636-EP2292620A2, 4636-EP2292621A1, 4636-EP2292625A1, 4636-EP2295402A2, 4636-EP2295408A1, 4636-EP2295412A1, 4636-EP2295413A1, 4636-EP2295415A1, 4636-EP2295422A2, 4636-EP2295429A1, 4636-EP2295433A2, 4636-EP2298305A1, 4636-EP2298761A1, 4636-EP2298776A1, 4636-EP2298780A1, 4636-EP2301544A1, 4636-EP2301932A1, 4636-EP2305627A1, 4636-EP2305636A1, 4636-EP2305640A2, 4636-EP2305652A2, 4636-EP2305655A2, 4636-EP2305668A1, 4636-EP2305675A1, 4636-EP2305677A1, 4636-EP2305688A1, 4636-EP2305689A1, 4636-EP2305695A2, 4636-EP2305696A2, 4636-EP2305697A2, 4636-EP2305698A2, 4636-EP2308812A2, 4636-EP2308828A2, 4636-EP2308840A1, 4636-EP2308844A2, 4636-EP2308845A2, 4636-EP2308846A2, 4636-EP2308849A1, 4636-EP2308850A1, 4636-EP2308852A1, 4636-EP2308866A1, 4636-EP2308872A1, 4636-EP2308876A1, 4636-EP2311464A1, 4636-EP2311801A1, 4636-EP2311802A1, 4636-EP2311803A1, 4636-EP2311820A1, 4636-EP2311823A1, 4636-EP2311825A1, 4636-EP2311836A1, 4636-EP2311837A1, 4636-EP2311840A1, 4636-EP2314574A1, 4636-EP2314576A1, 4636-EP2314580A1, 4636-EP2314584A1, 4636-EP2314588A1, 4636-EP2314590A1, 4636-EP2314593A1, 4636-EP2315502A1, 4636-EP2316829A1, 4636-EP2316832A1, 4636-EP2316833A1, 4636-EP2316834A1, 4636-EP2316835A1, 4636-EP2316974A1, 4636-EP2371795A1, 4636-EP2371814A1, 4636-EP2371823A1, 4636-EP2374790A1, 4636-EP2374791A1, 4636-EP2374792A1, 4636-EP2377845A1, 4636-EP2380869A1, 4636-EP2380870A1, Y-8606, 4-07-00-00641 (Beilstein Handbook Reference), I01-5864, T5957949, Chloroacetophenone (CN), liquid [UN1697] [Poison], Chloroacetophenone (CN), liquid [UN1697] [Poison], 3B3-035847, 108321-66-0

Removed Synonyms

Nutmeg butter, Nutmeg fat, Nutmeg oleoresin, Macis oil, Oil of nutmeg, Oil of mace, Oils, mace, Nutmeg butter fat, Nutmeg oil, fixed, 3′-Chloroacetophenone, 2 Chloroacetophenone, Fats, nutmeg butter, Nutmeg oil, expressed, MACE OIL, alpha Chloroacetophenone, omega Chloroacetophenone, Oils, myristica fragrans, Myristica fragrans houtt., Oil of nutmeg, expressed, 2 Chloro 1 phenylethanone, FEMA No. 2652, FEMA No. 2653, FEMA No. 2654, UNII-9R828X074Q, HSDB 1950, Mace (Myristica fragrans Houtt.), NCI-C56484, CID10757, c0095, Mace oil (Myristica fragrans Houtt.), EPA-E17300211, D002721, Mace oleoresin/extract (Myristica fragrans Houtt.), 2142-68-9, CAF, CAP, 4638-79-3, 8007-12-3

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