Phenacyl chloride: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 296402074

| Name =

| ImageFile = Chloroacetophenone.svg

| ImageSize = 180px

| ImageName = Skeletal formula

| ImageFile1 = Phenacyl-chloride-3D-balls.png

| ImageSize1 = 180px

| ImageName1 = Ball-and-stick model

| PIN = 2-Chloro-1-phenylethan-1-one

| OtherNames = 2-Chloro-1-phenylethanone<br />α-Chloroacetophenone<br />2-Chloroacetophenone<br />Chloromethyl phenyl ketone<br />Phenyl chloromethyl ketone<br/>CN<br/>Weeping gas<ref>Verma, K.S. [https://www.cengage.co.in/category/test-prep/jee-advanced/chemistry/course/physical-chemistry-for-joint-entrance-examination-jee-advanced-part-1-6h Cengage Physical Chemistry Part 1] {{Webarchive|url=https://web.archive.org/web/20210506233242/https://www.cengage.co.in/category/test-prep/jee-advanced/chemistry/course/physical-chemistry-for-joint-entrance-examination-jee-advanced-part-1-6h |date=2021-05-06 }}, Illustration 5.65</ref><br/>Mace

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 6285

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 532-27-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 88B5039IQG

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 105712

| PubChem = 10757

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10303

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

| SMILES = c1ccc(cc1)C(=O)CCl

}}

|Section2={{Chembox Properties

| C = 8 |H = 7 | O = 1 | Cl = 1

| Density = 1.324 g/cm³

| MeltingPtC = 54 to 56

| BoilingPtC = 244.5

| Solubility = insoluble

| Appearance = white to gray crystalline solid<ref name=PGCH/>

| Odor = pungent and irritating<ref name=PGCH/>

| VaporPressure = 0.005 mmHg (20&nbsp;°C)<ref name=PGCH/>

}}

|Section7={{Chembox Hazards

| MainHazards = Combustible<ref name=PGCH/>

| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}

| GHSSignalWord = danger

| HPhrases = {{HPhrases|H300|H311+H331|H315|H318|H334|H335}}

| PPhrases = {{PPhrases|P280|P301+P310+P330|P302+P352+P312|P304+P340+P311|P305+P351+P338+P310}}

| GHS_ref = <ref>GHS: [https://gestis.dguv.de/data?name=037810 GESTIS 037810]</ref>

| FlashPtC = 88

| AutoignitionPtC =

| NFPA-H = 3

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

| ExternalSDS =

| PEL = TWA 0.3 mg/m³ (0.05 ppm)<ref name=PGCH>{{PGCH|0119}}</ref>

| REL = TWA 0.3 mg/m³ (0.05 ppm)<ref name=PGCH/>

| IDLH = 15 mg/m³<ref name=PGCH/>

| LCLo = 417 mg/m³ (rat, 15 min)<br/>600 mg/m³ (mouse, 15 min)<br/>465 mg/m³ (rabbit, 20 min)<br/>490 mg/m³ (guinea pig, 30 min)<br/>159 mg/m³ (human, 20 min)<br/>850 mg/m³ (human, 10 min)<ref>{{IDLH|532274|alpha-Chloroacetophenone}}</ref>

}}

'''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'''.<ref name="doi10.1046/j.1365-2133.1999.02724.x">{{Cite journal | last1 = Treudler | first1 = R. | last2 = Tebbe | first2 = B. | last3 = Blume-Peytavi | first3 = U. | last4 = Krasagakis | first4 = K. | last5 = Orfanos | first5 = C. E. | title = Occupational contact dermatitis due to 2-chloracetophenone tear gas | doi = 10.1046/j.1365-2133.1999.02724.x | journal = British Journal of Dermatology | volume = 140 | issue = 3 | pages = 531–534 | year = 1999 | pmid = 10233281| s2cid = 45123933 }}</ref> 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.

Chloroacetophenone was first synthetized by Graebe in 1871 by passing chlorine into boiling [[acetophenone]].<ref>Graebe, C. (1871), Ueber eine neue Klasse von Alkoholen. Ber. Dtsch. Chem. Ges., 4: 34-35.</ref>

Phenacyl chloride is readily available and was first prepared by [[Photochlorination|chlorination]] of [[acetophenone]] vapour.<ref>{{cite journal |doi=10.1039/CA8783400392 |doi-access=free |title=Ketones of the aromatic group|journal=Journal of the Chemical Society, Abstracts |year=1878 |volume=34 |page=419 }}</ref> It may also be synthesized by the [[Friedel-Crafts acylation]] of [[benzene]] using [[chloroacetyl chloride]], with an [[aluminium chloride]] catalyst:<ref>{{OrgSynth | title = ω-Chloroisonitrosoacetophenone | author = Levin, N. | author2 = Hartung, W. H. | collvol = 3 | collvolpages = 191 | year = 1955 | prep = cv3p0191}}</ref>

:[[File:Preparation of phenacyl chloride.png|450px]]

It was investigated, but not used, during the [[World War I|First]] and [[Second World War]]s (it was used as a "green agent" by the former Japanese military during the Sino-Japanese War).

Because of CN's significantly greater toxicity,<ref name="xl">{{Cite journal | last1 = Ballantyne | first1 = B. | last2 = Swanston | first2 = D. W. | doi = 10.1007/BF01891962 | title = The comparative acute mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS) | journal = Archives of Toxicology | volume = 40 | issue = 2 | pages = 75–95 | year = 1978 | pmid = 350195| bibcode = 1978ArTox..40...75B | s2cid = 35150415 }}</ref> CN has largely been supplanted for military use by [[CS gas]]. Even though CN is still supplied to [[paramilitary]] and police forces in a small pressurized aerosol known as “[[Mace (spray)|Mace]]” or [[tear gas]], CN's use is falling because [[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 tissue]]s (a phenomenon known as a [[genericized trademark]]).

Like CS gas, this compound irritates the [[mucous membrane]]s (oral, nasal, [[conjunctiva]]l and [[tracheobronchial]]). Sometimes it can give rise to more generalized reactions such as [[fainting|syncope]], temporary loss of balance and orientation.<ref name="xl" /> More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent [[dermatitis]].<ref name="doi10.1046/j.1365-2133.1999.02724.x"/>

At high concentrations, CN may cause [[corneal epithelium|corneal epithelial]] damage and [[chemosis]]. It has also accounted for at least five deaths, which have resulted from [[pulmonary injury]] and/or [[asphyxia]].<ref>{{ cite journal | last = Blain | first = P. G. | title = Tear Gases and Irritant Incapacitants: 1-Chloroacetophenone, 2-Chlorobenzylidene Malononitrile and Dibenz&#91;b,f&#93;-1,4-Oxazepine | journal = Toxicological Reviews | volume = 22 | issue = 2 | pages = 103–110 | year = 2003 | pmid = 15071820 | doi=10.2165/00139709-200322020-00005| s2cid = 21164652 }}</ref>

[[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. <ref>doi=10.1096/fj.08-117812</ref><ref>doi=10.1016/j.taap.2008.04.005</ref>

{{Reflist}}

==External links==

*{{Commons category-inline}}

{{Transient receptor potential channel modulators}}

{{DEFAULTSORT:Phenacyl Chloride}}

[[Category:Organochlorides]]

[[Category:Aromatic ketones]]

[[Category:Acetophenones]]