Chloroacetophenone oxime

Chloroacetophenone oxime

Names
Preferred IUPAC name (1Z)-2-Chloro-N-hydroxy-1-phenylethan-1-imine
Identifiers
CAS Number	21572-32-7
3D model (JSmol)	Interactive image
ChemSpider	4899199
PubChem CID	5854981
CompTox Dashboard (EPA)	DTXSID90393433
InChI InChI=1S/C8H8ClNO/c9-6-8(10-11)7-4-2-1-3-5-7/h1-5,11H,6H2/b10-8-Key: VLXDSXLUNPBBOT-NTMALXAHSA-N
SMILES C1=CC=C(C=C1)C(=NO)CCl
Properties
Chemical formula	C8H8ClNO
Molar mass	169.61 g·mol−1
Melting point	88.5–89 °C (191.3–192.2 °F; 361.6–362.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chloroacetophenone oxime is the oxime derivative of chloroacetophenone. It's produced by reaction of chloroacetophenone with hydroxylamine. It has powerful lachrymatory and irritant effects.

References

1. ^ Sartori, Mario (1939). The War Gases (PDF). p. 160.

v t e Agents used in chemical warfare incapacitation riot control
Blood agents	Cyanogen Cyanogen bromide Cyanogen chloride (CK) Hydrogen cyanide (AC) Arsine Cacodyl cyanide Cacodyl oxide Hydrogen sulfide Phosphine Carbon monoxide Phosphorus trifluoride Methyl cyanoformate Iron pentacarbonyl Nickel tetracarbonyl 2,3,7,8-Tetrachlorodibenzodioxin Glycolonitrile Lactonitrile Acetone cyanohydrin Stibine Chloral cyanohydrin
Blister agents	Arsenicals Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3) Sulfur mustards Levinstein mustard (EA-229) T Q CEES Nitrogen mustards HN1 HN2 HN3 TL-301 Nettle agents Phosgene oxime (CX) Other KB-16 Dibutylchloromethyltin chloride Selenium oxychloride
Nerve agents	G-agents Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin V-agents EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7) GV agents GV (EA-5365) Novichok agents A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042 Carbamates Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10) Other Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI Precursors Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG
Neurotoxins	Anatoxin-a Saxitoxin (TZ) Bungarotoxin Botulinum toxin (BTX) Tetanospasmin (TeNT) Ryanodine Ciguatoxin (CTX) Guanitoxin (GTX) Chlorophenylsilatrane Palytoxin (PTX) Maitotoxin (MTX) Tetrodotoxin Aconitine Brevetoxin (PbTX) Strychnine Antillatoxin (ATX) Tetraethyllead Dimethylmercury HN1 hydrochloride HN2 hydrochloride HN3 hydrochloride A-8564 Picrotoxin Sulfuryl fluoride Tremorine Oxotremorine Batrachotoxin Tetramethylenedisulfotetramine (TETS) Bicyclic phosphates IPTBO TBPO TBPS Cloflubicyne Trimethylolpropane phosphite Domoic acid
Pulmonary/ choking agents	Chlorine Bromine Phosgene (CG) Fluorine Perfluoroisobutene Chloropicrin (PS) Dimethyl(trifluoromethylthio)arsine Diphosgene (DP) Disulfur decafluoride (Z) Acrolein Ethyl bromoacetate Perchloromethyl mercaptan Phenylcarbylamine chloride Tetranitromethane Tetrachlorodinitroethane Chlorine trifluoride Perchloryl fluoride Cadmium oxide Cadmium chloride Mercuric chloride Selenium dioxide Selenoyl fluoride Trifluoronitrosomethane Trichloronitrosomethane Nitric oxide Nitrogen dioxide Dinitrogen tetroxide Sulfur dioxide Phosphorus trichloride Methyl isocyanate Ethenone Methyl vinyl ketone Trifluoroacetyl chloride Salcomine Fluomine Uranium hexafluoride Diborane Green Cross
Vomiting agents	Adamsite (DM) Chloropicrin Litharge-glycerine Diphenylchlorarsine Diphenylcyanoarsine Cacodyl cyanide o-Dianisidine
Incapacitating agents	BZ (CS-4030) Apomorphine Butyrophenone EA-4941 (CS-4640) Etorphine EA-2092 CS-4297 Etoxadrol Dimethylheptylpyran (DMHP) EA-2148 EA-3167 EA-3443 Pethidine EA-3580 Ibogaine EA-3834 Kolokol-1 LSD-25 PAVA spray Psilocybin Sleeping gas Carfentanil JB-318 JB-336 CS-27349 CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 Benperidol Desflurane Enflurane Bufotenin Isoflurane Halothane Sevoflurane Pentazocine Procarbazine Fluphenazine Chlorpromazine
Lachrymatory agents	Xylyl bromide Pepper spray (OC) Mace (spray) CN CS CR CNS Benzyl chloride Benzyl bromide Benzyl iodide Bromobenzyl cyanide Thiophosgene Chloroacetone Bromoacetone Bromomethyl ethyl ketone Acrolein Phenacyl bromide Chloroacetophenone oxime Ethyl bromoacetate Ethyl iodoacetate Iodoacetone Allyl isothiocyanate Hexamethylene diisocyanate Crotonaldehyde
Malodorant agents	Thioacetone Allicin Skatole Cadaverine Putrescine
Cornea-clouding agents	Lewisite CX KB-16 Methyl cyanoacrylate N-Methylmorpholine Allyl alcohol Osmium tetroxide Acrolein
Biological toxins	Abrin Aconitine Cyclopiazonic acid Histrionicotoxins Aflatoxins Anatoxin-a Batrachotoxin Botulinum toxin Brevetoxin Ciguatoxin Domoic acid Enterotoxin type B Grayanotoxin Guanitoxin Maitotoxin Modeccin Palytoxin Ricin Saxitoxin Shiga toxin T-2 mycotoxin Tetanospasmin Tetrodotoxin Volkensin Veratridine
Other	Methyl fluoroacetate Napalm (variants and mixtures) Fluoroethyl fluoroacetate Depleted uranium post-combustion uranium oxides Plutonium and its compounds Polonium White phosphorus
List of chemical warfare agents CB military symbol

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