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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m C N g a s )
Phenacyl chloride
Names
Preferred IUPAC name
2-Chloro-1-phenylethan-1-one
Other names
2-Chloro-1-phenylethanone α-Chloroacetophenone 2-Chloroacetophenone Chloromethyl phenyl ketone Phenyl chloromethyl ketoneCN Weeping gas[1] Mace
Identifiers
CAS Number
3D model (JSmol )
ChEMBL
ChemSpider
ECHA InfoCard
100.007.757
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C8H7ClO/c9-6-8(10 )7-4-2-1-3-5-7/h1-5H,6H2
Properties
Chemical formula
C 8 H 7 Cl O
Molar mass
154.59 g·mol−1
Appearance
white to gray crystalline solid[2]
Odor
pungent and irritating[2]
Density
1.324 g/cm3
Melting 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
insoluble
Vapor pressure
0.005 mmHg (20 °C)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Combustible[2]
GHS labelling :[4]
Pictograms
Signal word
Danger
Hazard statements
H300 , H311+H331 , H315 , H318 , H334 , H335
Precautionary statements
P280 , P301+P310+P330 , P302+P352+P312 , P304+P340+P311 , P305+P351+P338+P310
NFPA 704 (fire diamond)
Flash point
88 °C (190 °F; 361 K )
Lethal dose or concentration (LD, LC):
LC Lo (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).
Infobox references
Chemical compound
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.
Preparation
[ edit ]
Chloroacetophenone 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]
Riot control agent
[ edit ]
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 [clarification needed ] 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 ]
^ "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). "ω-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.2008.04.005
External links
[ edit ]
t
e
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (ginger , Sichuan and melegueta peppers )
Acrolein
Allicin (garlic )
Allyl isothiocyanate (mustard , radish , horseradish , wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis )
Cannabidiol (cannabis )
Cannabigerol (cannabis )
Cinnamaldehyde (cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin )
Curcumin (turmeric )
Dehydroligustilide (celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper )
Shogaols (ginger , Sichuan and melegueta peppers )
Tear gases
Tetrahydrocannabinol (cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
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12S-HETE
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13-oxoODE
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α-Sanshool (ginger , Sichuan and melegueta peppers )
Allicin (garlic )
AM404
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Bisandrographolide (Andrographis paniculata )
Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil )
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Diacyl glycerol
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Eugenol (basil , clove )
Evodiamine (Euodia ruticarpa )
Gingerols (ginger )
GSK1016790A
Heat
Hepoxilin A3
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Homodihydrocapsaicin (chili pepper )
Incensole (incense )
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Low pH (acidic conditions)
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N-Arachidonoyl dopamine
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Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., 4α-PDD )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (Ruta graveolens )
Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii )
Shogaols (ginger , Sichuan and melegueta peppers )
Tetrahydrocannabivarin (cannabis )
Thymol (thyme , oregano )
Tinyatoxin (Euphorbia resinifera /pooissonii )
Tramadol
Vanillin (vanilla )
Zucapsaicin
Blockers
See also: Receptor/signaling modulators • Ion channel modulators
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Phenacyl_chloride&oldid=1234472205 "
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