| 词条 | Phenacyl chloride |
| 释义 |
| 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 α-Chloroacetophenone 2-Chloroacetophenone Chloromethyl phenyl ketone Phenyl chloromethyl ketone CN Weeping gas[1] Mace |Section1={{Chembox Identifiers | IUPHAR_ligand = 6285 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 532-27-4 | 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[2] | Odor = pungent and irritating[2] | VaporPressure = 0.005 mmHg (20 °C)[2] |Section7={{Chembox Hazards | EUClass = {{Hazchem T}} | MainHazards = Combustible[2] | FlashPtC = 88 | AutoignitionPtC = | NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | ExternalSDS = | PEL = TWA 0.3 mg/m3 (0.05 ppm)[2] | REL = TWA 0.3 mg/m3 (0.05 ppm)[2] | IDLH = 15 mg/m3[2] | LCLo = 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] }} 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.[4] It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−. PreparationPhenacyl chloride is readily available commercially. It may be synthesized by the Friedel-Crafts acylation of benzene using chloroacetyl chloride, with an aluminium chloride catalyst:[5] Riot control agentIt was investigated, but not used, during the First and Second World Wars. Because of its significantly greater toxicity,[6] 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).{{citation needed|date=July 2012}} 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.[6] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis.[4] 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.[7] References1. ^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], Illustration 5.65 2. ^1 2 3 4 5 6 {{PGCH|0119}} 3. ^{{IDLH|532274|alpha-Chloroacetophenone}} 4. ^1 {{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| pmc = }} 5. ^{{OrgSynth | title = ω-Chloroisonitrosoacetophenone | author = Levin, N.; Hartung, W. H. | collvol = 3 | collvolpages = 191 | year = 1955 | prep = cv3p0191}} 6. ^1 {{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| pmc = }} 7. ^{{ cite journal | last = Blain | first = P. G. | title = Tear Gases and Irritant Incapacitants: 1-Chloroacetophenone, 2-Chlorobenzylidene Malononitrile and Dibenz[b,f]-1,4-Oxazepine | journal = Toxicological Reviews | volume = 22 | issue = 2 | pages = 103–110 | year = 2003 | pmid = 15071820 | url = http://www.ingentaconnect.com/content/adis/txr/2003/00000022/00000002/art00005 | doi=10.2165/00139709-200322020-00005}} External links
4 : Riot control agents|Lachrymatory agents|Organochlorides|Aromatic ketones |
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