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chloroacetone wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 properties 2 synthesis 3 applications 4 purification 5 transportation regulations 6 see also 7 references 8 external links toggle the table of contents chloroacetone 20 languages تۆرکجه čeština deutsch esperanto español فارسی suomi français bahasa indonesia 日本語 nederlands polski română русский srpskohrvatski српскохрватски српски srpski தமிழ் türkçe اردو 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chloroacetone names preferred iupac name 1 chloropropan 2 one other names acetonyl chloride chloropropanone 1 chloro 2 propanone monochloroacetone 1 chloro 2 ketopropane 1 chloro 2 oxypropane un 1695 identifiers cas number 78 95 5 y 3d model jsmol interactive image beilstein reference 605369 chebi chebi 47220 y chemspider 6323 y echa infocard 100 001 056 ec number 201 161 1 pubchem cid 6571 rtecs number uc0700000 unii 60ztr74268 y comptox dashboard epa dtxsid0021547 inchi inchi 1s c3h5clo c1 3 5 2 4 h2h2 1h3 y key bullhnjgppouox uhfffaoysa n y key bullhnjgppouox uhfffaoyay smiles clcc o c properties chemical formula c 3 h 5 cl o molar mass 92 52 g mol 1 appearance colorless liquid oxidizes to amber density 1 123 g cm 3 melting point 44 5 c 48 1 f 228 7 k boiling point 119 c 246 f 392 k solubility in water 10 g 100 ml at 20 c solubility miscible with alcohol ether chloroform vapor pressure 1 5 kpa magnetic susceptibility χ 50 9 10 6 cm 3 mol dipole moment 2 36 hazards flash point 35 c 95 f 308 k autoignition temperature 610 c 1 130 f 883 k explosive limits 3 4 1 lethal dose or concentration ld lc ld 50 median dose 100 mg kg rats oral 2 except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound chloroacetone is a liquid a chemical compound with the formula c h 3 c o ch 2 cl regulated for its potential as a tear gas it is primarily a chemical intermediate in commerce properties edit at stp it is a colorless liquid with a pungent odor 3 on exposure to light it turns to a dark yellow amber color 4 it was used as a tear gas in world war i 5 synthesis edit chloroacetone may be synthesized from the reaction between chlorine and diketene or by the chlorination of acetone applications edit chloroacetone is primarily an intermediate in chemical manufacture in the early 2000s it was used to make dye couplers for colour film photography 2 in the pharmaceutical industry it is a precursor to phenoxyacetone 6 it is also used in the feist benary synthesis of furans 7 purification edit chloroacetone purchased from commercial suppliers contains 5 impurities including mesityl oxide which is not removed by distillation mesityl oxide can be oxidized using acidified kmno 4 to form a diol followed by separation with ether which is removed on subsequent distillation 8 transportation regulations edit transportation of unstabilized chloroacetone has been banned in the united states by the us department of transportation stabilized chloroacetone is in hazard class 6 1 poison inhalation hazard its un number is 1695 see also edit bromoacetone dichloroacetone fluoroacetone hexachloroacetone use of poison gas in world war i references edit icsc neng0760 international chemical safety cards who ipcs ilo cdc niosh center for disease control 2006 10 11 retrieved 2009 04 17 1 2 hathaway gloria j proctor nick h 2004 proctor and hughes chemical hazards of the workplace 5 ed wiley interscience pp 143 144 isbn 978 0 471 26883 3 retrieved 2009 04 16 occupational safety and health guideline for chloroacetone u s department of labor occupational safety health administration archived from the original on 2013 05 03 retrieved 2008 06 06 chloroacetone international programme on chemical safety retrieved 2008 06 06 haber ludwig fritz 1986 the poisonous cloud chemical warfare in the first world war oxford university press isbn 0 19 858142 4 hurd charles d perletz percy 1946 aryloxyacetones1 journal of the american chemical society 68 1 38 40 doi 10 1021 ja01205a012 issn 0002 7863 li jie jack corey e j 2004 name reactions in heterocyclic chemistry wiley interscience p 160 isbn 978 0 471 30215 5 retrieved 2009 04 16 phys chem chem phys 2000 2 237 245 external links edit the halogenation of carbonyls 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 q 1 3 dichloroacetone other kb 16 dibutylchloromethyltin chloride selenium oxychloride phenacyl bromide dimethyl acetylenedicarboxylate dimethyl fumarate chalcone hydrazone methylnitronitrosoguanidine norcantharidin cantharidin t 2 mycotoxin do nerve agents g agents tabun ga sarin gb chlorosarin clgb thiosarin sgb soman gd chlorosoman clgd ethylsarin ge gh cyclosarin gf gp gs fluorotabun ea 1356 ea 4352 crotylsarin v agents ea 2192 ea 3148 ve vg vm vp vr vs vx vt ea 1763 chinese vx v sub x gd 7 gv agents gv ea 5365 ea 5488 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 mevinphos aldicarb phospholine r 16661 vr 56 ro 3 0422 methanesulfonyl fluoride dimefox tl 792 paraoxon mspi fumette 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 dc nitromethane opa mixture phosphoryl chloride phosphorus pentachloride phosphorus trichloride th pinacolone pinacolyl alcohol phenacyl chloride ql ql sulfide 2 4 5 trichlorophenol 3 3 5 trimethylcyclohexanol triethyl phosphite trimethyl phosphite tc tg neurotoxins anatoxin a saxitoxin tz coniine bungarotoxin botulinum toxin btx tetanospasmin tent ryanodine ciguatoxin ctx guanitoxin gtx chlorophenylsilatrane palytoxin ptx maitotoxin mtx tetrodotoxin veratridine aconitine brevetoxin pbtx strychnine antillatoxin atx tetraethyllead dimethylmercury hn1 hydrochloride hn2 hydrochloride hn3 hydrochloride a 8564 picrotoxin mptp bis chloromethyl ether gelsemine epibatidine 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 antimony potassium tartrate lobeline incapacitating agents bz cs 4030 apomorphine butyrophenone ea 4941 cs 4640 etorphine ea 2092 cs 4297 etoxadrol dimethylheptylpyran dmhp canbisol ea 2148 remifentanil ea 2219 ea 3167 nicotine ea 3443 methaqualone pethidine ea 3580 ibogaine ea 3834 kolokol 1 lsd 25 pava spray psilocybin acetonylacetone 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 phorbol esters ingenol mebutate rtx 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 croton oil drc 5593 malodorant agents thioacetone butyl mercaptan allicin skatole cadaverine putrescine cornea clouding agents lewisite cx kb 16 methyl cyanoacrylate n methylmorpholine allyl alcohol osmium tetroxide acrolein cacodyl cyanide dimethyl diglycolate biological toxins abrin aconitine cyclopiazonic acid histrionicotoxins aflatoxins anatoxin a batrachotoxin ea 3000 brevetoxin ciguatoxin domoic acid enterotoxin type b grayanotoxin guanitoxin maitotoxin modeccin ea 3940 ricin saxitoxin shiga toxin t 2 mycotoxin tetanospasmin tetrodotoxin volkensin veratridine tumor promoting agents phorbol esters 12 o tetradecanoylphorbol 13 acetate croton oil bis chloromethyl ether do 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 authority control databases gnd retrieved from https en wikipedia org w index php title chloroacetone oldid 1320739870 categories organochlorides lachrymatory agents chemical weapons in world war i ketones hidden categories articles without inchi source articles without kegg source echa infocard id from wikidata articles containing unverified chemical infoboxes chembox image size set articles with short description short description matches wikidata this page was last edited on 6 november 2025 at 14 03 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents chloroacetone 20 languages add topic