Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN.[5] It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−. Chloroacetophenone is thermally stable, and is the only tear agent that is distillable at ambient conditions.
It was investigated, but not used, during the First and Second World Wars (it was used as a "green agent" by the former Japanese military during the Sino-Japanese War).
Because of its significantly greater toxicity,[9] it has largely been supplanted by CS gas. Even though CN is still supplied to paramilitary and police forces in a small pressurized aerosol known as “Mace” or tear gas, its use is falling as pepper spray both works and disperses more quickly than CN and is less toxic than CN.
The term "Mace" came into being because it was the brand-name invented by one of the first American manufacturers of CN aerosol sprays. Subsequently, in the United States, Mace became synonymous with tear-gas sprays in the same way that Kleenex has become strongly associated with facial tissues (a phenomenon known as a genericized trademark).
Like CS gas, this compound irritates the mucous membranes (oral, nasal, conjunctival and tracheobronchial). Sometimes it can give rise to more generalized reactions such as syncope, temporary loss of balance and orientation.[9] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.[5]
TRPA1 (Transient Receptor Potential-Ankyrin 1) ion channel expressed on nociceptors (especially trigeminal) has been implicated as the site of action for CN, in vivo and in vitro. [11][12]
Referencesedit
^Verma, K.S. Cengage Physical Chemistry Part 1 2021-05-06 at the Wayback Machine, Illustration 5.65
^ abTreudler, R.; Tebbe, B.; Blume-Peytavi, U.; Krasagakis, K.; Orfanos, C. E. (1999). "Occupational contact dermatitis due to 2-chloracetophenone tear gas". British Journal of Dermatology. 140 (3): 531–534. doi:10.1046/j.1365-2133.1999.02724.x. PMID 10233281. S2CID 45123933.
^Graebe, C. (1871), Ueber eine neue Klasse von Alkoholen. Ber. Dtsch. Chem. Ges., 4: 34-35.
^"Ketones of the aromatic group". Journal of the Chemical Society, Abstracts. 34: 419. 1878. doi:10.1039/CA8783400392.
^Levin, N.; Hartung, W. H. (1955). "ω-Chloroisonitrosoacetophenone". Organic Syntheses; Collected Volumes, vol. 3, p. 191.
^ abBallantyne, B.; Swanston, D. W. (1978). "The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS)". Archives of Toxicology. 40 (2): 75–95. doi:10.1007/BF01891962. PMID 350195. S2CID 35150415.
^Blain, P. G. (2003). "Tear Gases and Irritant Incapacitants: 1-Chloroacetophenone, 2-Chlorobenzylidene Malononitrile and Dibenz[b,f]-1,4-Oxazepine". Toxicological Reviews. 22 (2): 103–110. doi:10.2165/00139709-200322020-00005. PMID 15071820. S2CID 21164652.
Media related to Phenacyl chloride at Wikimedia Commons
April 09, 2024
phenacyl, chloride, also, commonly, known, chloroacetophenone, substituted, acetophenone, useful, building, block, organic, chemistry, apart, from, that, been, historically, used, riot, control, agent, where, designated, should, confused, with, cyanide, anothe. Phenacyl chloride also commonly known as chloroacetophenone is a substituted acetophenone It is a useful building block in organic chemistry Apart from that it has been historically used as a riot control agent where it is designated CN 5 It should not be confused with cyanide another agent used in chemical warfare which has the chemical structure CN Chloroacetophenone is thermally stable and is the only tear agent that is distillable at ambient conditions Phenacyl chloride NamesPreferred IUPAC name 2 Chloro 1 phenylethan 1 oneOther names 2 Chloro 1 phenylethanonea Chloroacetophenone2 ChloroacetophenoneChloromethyl phenyl ketonePhenyl chloromethyl ketoneCNWeeping gas 1 MaceIdentifiersCAS Number 532 27 4 Y3D model JSmol Interactive imageChEMBL ChEMBL105712 NChemSpider 10303 NECHA InfoCard 100 007 757IUPHAR BPS 6285PubChem CID 10757UNII 88B5039IQG YCompTox Dashboard EPA DTXSID9020293InChI InChI 1S C8H7ClO c9 6 8 10 7 4 2 1 3 5 7 h1 5H 6H2SMILES c1ccc cc1 C O CClPropertiesChemical formula C 8H 7Cl OMolar mass 154 59 g mol 1Appearance white to gray crystalline solid 2 Odor pungent and irritating 2 Density 1 324 g cm3Melting point 54 to 56 C 129 to 133 F 327 to 329 K Boiling point 244 5 C 472 1 F 517 6 K Solubility in water insolubleVapor pressure 0 005 mmHg 20 C 2 HazardsOccupational safety and health OHS OSH Main hazards Combustible 2 GHS labelling 4 PictogramsSignal word DangerHazard statements H300 H311 H331 H315 H318 H334 H335Precautionary statements P280 P301 P310 P330 P302 P352 P312 P304 P340 P311 P305 P351 P338 P310NFPA 704 fire diamond 310Flash point 88 C 190 F 361 K Lethal dose or concentration LD LC LCLo lowest published 417 mg m3 rat 15 min 600 mg m3 mouse 15 min 465 mg m3 rabbit 20 min 490 mg m3 guinea pig 30 min 159 mg m3 human 20 min 850 mg m3 human 10 min 3 NIOSH US health exposure limits PEL Permissible TWA 0 3 mg m3 0 05 ppm 2 REL Recommended TWA 0 3 mg m3 0 05 ppm 2 IDLH Immediate danger 15 mg m3 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Riot control agent 3 References 4 External linksPreparation editChloroacetophenone was first synthetized by Graebe in 1871 by passing chlorine into boiling acetophenone 6 Phenacyl chloride is readily available and was first prepared by chlorination of acetophenone vapour 7 It may also be synthesized by the Friedel Crafts acylation of benzene using chloroacetyl chloride with an aluminium chloride catalyst 8 nbsp Riot control agent editIt was investigated but not used during the First and Second World Wars it was used as a green agent by the former Japanese military during the Sino Japanese War Because of its significantly greater toxicity 9 it has largely been supplanted by CS gas Even though CN is still supplied to paramilitary and police forces in a small pressurized aerosol known as Mace or tear gas its use is falling as pepper spray both works and disperses more quickly than CN and is less toxic than CN The term Mace came into being because it was the brand name invented by one of the first American manufacturers of CN aerosol sprays Subsequently in the United States Mace became synonymous with tear gas sprays in the same way that Kleenex has become strongly associated with facial tissues a phenomenon known as a genericized trademark Like CS gas this compound irritates the mucous membranes oral nasal conjunctival and tracheobronchial Sometimes it can give rise to more generalized reactions such as syncope temporary loss of balance and orientation 9 More rarely cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis 5 At high concentrations CN may cause corneal epithelial damage and chemosis It has also accounted for at least five deaths which have resulted from pulmonary injury and or asphyxia 10 TRPA1 Transient Receptor Potential Ankyrin 1 ion channel expressed on nociceptors especially trigeminal has been implicated as the site of action for CN in vivo and in vitro 11 12 References edit Verma K S Cengage Physical Chemistry Part 1 Archived 2021 05 06 at the Wayback Machine Illustration 5 65 a b c d e f g NIOSH Pocket Guide to Chemical Hazards 0119 National Institute for Occupational Safety and Health NIOSH alpha Chloroacetophenone Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH GHS GESTIS 037810 a b Treudler R Tebbe B Blume Peytavi U Krasagakis K Orfanos C E 1999 Occupational contact dermatitis due to 2 chloracetophenone tear gas British Journal of Dermatology 140 3 531 534 doi 10 1046 j 1365 2133 1999 02724 x PMID 10233281 S2CID 45123933 Graebe C 1871 Ueber eine neue Klasse von Alkoholen Ber Dtsch Chem Ges 4 34 35 Ketones of the aromatic group Journal of the Chemical Society Abstracts 34 419 1878 doi 10 1039 CA8783400392 Levin N Hartung W H 1955 w Chloroisonitrosoacetophenone Organic Syntheses Collected Volumes vol 3 p 191 a b Ballantyne B Swanston D W 1978 The comparative acute mammalian toxicity of 1 chloroacetophenone CN and 2 chlorobenzylidene malononitrile CS Archives of Toxicology 40 2 75 95 doi 10 1007 BF01891962 PMID 350195 S2CID 35150415 Blain P G 2003 Tear Gases and Irritant Incapacitants 1 Chloroacetophenone 2 Chlorobenzylidene Malononitrile and Dibenz b f 1 4 Oxazepine Toxicological Reviews 22 2 103 110 doi 10 2165 00139709 200322020 00005 PMID 15071820 S2CID 21164652 doi 10 1096 fj 08 117812 doi 10 1016 j taap 2008 04 005External links edit nbsp Media related to Phenacyl chloride at Wikimedia Commons Retrieved from https en wikipedia org w index php title Phenacyl chloride amp oldid 1197668864, wikipedia, wiki, book, books, library,
