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Revision as of 01:27, 12 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox vali← Previous edit		Latest revision as of 17:49, 3 April 2022 edit undo1234qwer1234qwer4 (talk | contribs)Extended confirmed users, Page movers197,958 editsm correct param for MOS:REFSPACE (cf. Special:Diff/1065499921) (via WP:JWB)
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			{{Distinguish|Acetyl chloride|Chloroacetic acid}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 415462460
			| Watchedfields = changed
⚫	| ImageFile = Chloroacetyl chloride.svg
		⚫	| verifiedrevid = 444365675
⚫	| ImageSize = 150px
		⚫	| ImageFile = Chloroacetyl chloride.svg
⚫	| ImageName = Skeletal formula
		⚫	| ImageSize = 150px
⚫	| ImageFile1 = Chloroacetyl-chloride-3D-balls.png
		⚫	| ImageName = Skeletal formula
⚫	| ImageSize1 = 170px
		⚫	| ImageFile1 = Chloroacetyl-chloride-3D-balls.png
⚫	| ImageName1 = ball-and-stick model
		⚫	| ImageSize1 = 170px
	| IUPACName = chloroacetyl chloride
		⚫	| ImageName1 = ball-and-stick model
	| OtherNames =
			| PIN = Chloroacetyl chloride
			| OtherNames = 2-Chloroacetyl chloride<br />Chloroacetic acid chloride<br />Chloroacetic chloride<br />Monochloroacetyl chloride
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| ChemSpiderID = 6329		| ChemSpiderID = 13856283
		⚫	| SMILES = C(C(=O)Cl)Cl
⚫	| CASNo=79-04-9
			| InChI = 1/C2H2Cl2O/c3-1-2(4)5/h1H2
⚫	| CASNo_Ref = {{cascite}}
			| InChIKey = VGCXGMAHQTYDJK-UHFFFAOYAB
	| PubChem=6577
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| SMILES=C(C(=O)Cl)Cl
			| StdInChI = 1S/C2H2Cl2O/c3-1-2(4)5/h1H2
⚫	| EINECS=201-171-6
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = VGCXGMAHQTYDJK-UHFFFAOYSA-N
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| CASNo =79-04-9
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = K5UML06YUO
			| PubChem =6577
		⚫	| EINECS =201-171-6
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C14859		| KEGG = C14859
			| ChEMBL = 3187685
			| ChEBI = 34624
			| RTECS = AO6475000
			| UNNumber = 1752
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| C = 2 | H = 2 | Cl = 2 | O = 1		| C=2 | H=2 | Cl=2 | O=1
	| Appearance=Colorless liquid		| Appearance =Colorless to yellow liquid
	| Density=1.42 g/mL		| Density =1.42 g/mL
	| MeltingPtC=-22		| MeltingPtC =-22
	| BoilingPtC=106		| BoilingPtC =106
	| Solubility=Reacts		| Solubility = Reacts
			| VaporPressure = 19 mmHg (20°C)<ref name=PGCH/>
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| EUClass = {{Hazchem T}} {{Hazchem N}} {{Hazchem C}}		| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}{{GHS09}}
			| GHSSignalWord = Danger
	| FlashPt=
			| HPhrases = {{H-phrases|301|311|314|331|372|400}}
	| Autoignition=
			| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|314|321|322|330|361|363|391|403+233|405|501}}
⚫	}}
			| NFPA-H = 3
			| NFPA-F = 0
			| NFPA-I = 1
			| NFPA_ref = <ref name=OSHA>{{cite web|url=https://www.osha.gov/chemicaldata/685|title=OSHA Occupational Chemical Database|publisher=Occupational Safety and Health Administration (OSHA)}}</ref>
			| FlashPt = noncombustible
			| FlashPt_ref = <ref name=PGCH/>
			| AutoignitionPt =
			| PEL = none<ref name=PGCH>{{PGCH|0120}}</ref>
			| IDLH = N.D.<ref name=PGCH/>
			| REL = TWA 0.05 ppm (0.2 mg/m<sup>3</sup>)<ref name=PGCH/>
		⚫	}}
	}}		}}
	'''Chloroacetyl chloride''' is a chlorinated ]. It is a ], making it a useful building block chemical.		'''Chloroacetyl chloride''' is a chlorinated ]. It is a ], making it a useful building block chemical.
	==Production==		==Production==
	Industrially, it is produced by the ] of ], ] of ], or the addition of ] to ].<ref name = worsham>{{cite book | editor =Zoeller, Joseph R.; Agreda, V. H., eds. |title=Acetic acid and its derivatives |publisher=M. Dekker |location=New York |year=1993 | chapter = 15. Halogenated Derivatives | author = Paul R. Worsham |isbn=0-8247-8792-7 | pages = 288–298 | url = http://books.google.com/?id=3MjdGp1v1YIC&pg=RA2-PA288 | format = ] excerpt}}</ref> It may be prepared from ] and ], ], or ].		Industrially, it is produced by the ] of ], ] of ], or the addition of ] to ].<ref name="worsham">{{cite book |editor1=Zoeller, Joseph R. |editor2=Agreda, V. H. |title=Acetic acid and its derivatives |publisher=M. Dekker |location=New York |year=1993 | chapter = 15. Halogenated Derivatives | author = Paul R. Worsham |isbn=0-8247-8792-7 | pages = 288–298 | chapter-url = https://books.google.com/books?id=3MjdGp1v1YIC&pg=RA2-PA288 | chapter-format = ] excerpt}}</ref> It may be prepared from ] and ], ], or ].
	==Reactions==		==Reactions==
	Chloroacetyl chloride is bifunctional—the acyl chloride easily forms ]s<ref>{{OrgSynth | prep = cv3p0141 | collvol = 3 | collvolprep = 141 | year = 1955 | title = tert-Butyl acetate | author = Robert H. Baker and Frederick G. Bordwell}}</ref> and ]s, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of ] is illustrative:<ref>{{cite journal | journal = ] | volume = 76 | issue = 11 | year = 1999 | pages = 1557 | author = T. J. Reilly | title = The Preparation of Lidocaine | url = http://jchemed.chem.wisc.edu/Journal/Issues/1999/Nov/abs1557.html | doi = 10.1021/ed076p1557}}</ref>		Chloroacetyl chloride is bifunctional—the acyl chloride easily forms ]s<ref>{{OrgSynth | prep = cv3p0141 | collvol = 3 | collvolprep = 141 | year = 1955 | title = tert-Butyl acetate | author = Robert H. Baker and Frederick G. Bordwell}}</ref> and ]s, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of ] is illustrative:<ref>{{cite journal | journal = ] | volume = 76 | issue = 11 | year = 1999 | pages = 1557 | author = T. J. Reilly | title = The Preparation of Lidocaine | url = http://jchemed.chem.wisc.edu/Journal/Issues/1999/Nov/abs1557.html | doi = 10.1021/ed076p1557| bibcode = 1999JChEd..76.1557R }}</ref>
	:]		:]
	==Applications==		==Applications==
	The major use of chloroacetyl chloride is as an intermediate in the production of ] and ]; an estimated 100 million pounds are used annually. Some chloroacetyl chloride is also used to produce ], another chemical intermediate, also used as a tear gas.<ref name = worsham/> Phenacyl chloride is synthesized in a ] of ], with an ] catalyst:<ref>{{OrgSynth | title = ω-Chloroisonitrosoacetophenone | author = Nathan Levin and Walter H. Hartung | collvol = 3 | collvolpages = 191 | year = 1955 | prep = cv3p0191}}</ref>		The major use of chloroacetyl chloride is as an intermediate in the production of herbicides in the chloroacetanilide family including ], ], ] and ]; an estimated 100 million pounds are used annually. Some chloroacetyl chloride is also used to produce ], another chemical intermediate, also used as a tear gas.<ref name = worsham/> ] is synthesized in a ] of ], with an ] catalyst:<ref>{{OrgSynth | title = ω-Chloroisonitrosoacetophenone | author = Nathan Levin and Walter H. Hartung | collvol = 3 | collvolpages = 191 | year = 1955 | prep = cv3p0191}}</ref>
	:]		:]
			With ], it is used for the synthesis of ].
	==Safety==		==Safety==
	Like other acyl chlorides, reaction with other protic compounds such as amines, alcohols, and water generates ], making it a ].		Like other acyl chlorides, reaction with other protic compounds such as amines, alcohols, and water generates ], making it a ].
			There is no regulated ] set by the ]. However, the ] has set a ] at 0.05 ppm over an eight-hour work day.<ref>{{cite web|title=NIOSH Pocket Guide to Chemical Hazards|url=https://www.cdc.gov/niosh/npg/npgd0120.html|publisher=Centers for Disease Control and Prevention|year=2011}}</ref>
	==References==		==References==
			{{reflist}}
	<references/>
	]		]
			]
	]
	]
	]