| Revision as of 19:56, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472742027 of page Acetyl_chloride for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 23:48, 10 December 2024 edit Graeme Bartlett (talk | contribs)Administrators249,716 edits drugbank |
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{{short description|Organic compound (CH₃COCl)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Distinguish|Chloroacetic acid|Chloroacetyl chloride|Acetylcholine|Actinium(III) chloride}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 446282072 |
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| Watchedfields = changed |
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| Reference=<ref>'']'', 11th Edition, '''79'''.</ref> |
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| verifiedrevid = 477239934 |
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| Name = Acetyl chloride |
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| Reference=<ref>'']'', 11th Edition, '''79'''.</ref> |
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| ImageFileL1 = Acetyl chloride-2D-Skeletal.png |
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| Name = Acetyl chloride |
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| ImageSizeL1 = 100px |
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| ImageFileL1 = Acetyl-chloride_skeletal.svg |
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| ImageNameL1 = Skeletal formula of acetyl chloride |
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| ImageNameL1 = Skeletal formula of acetyl chloride |
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| ImageFileR1 = Acetyl-chloride-3D-balls.png |
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| ImageFileR1 = Acetyl-chloride-3D-balls.png |
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| ImageSizeR1 = 100px |
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| ImageNameR1 = Ball-and-stick model of acetyl chloride |
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| ImageNameR1 = Ball-and-stick model of acetyl chloride |
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| ImageFile2 = Acetyl-chloride-3D-vdW.png |
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| ImageFile2 = Acetyl-chloride-3D-vdW.png |
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| ImageSize2 = 120px |
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| ImageSize2 = 120px |
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| ImageName2 = Space-filling model of acetyl chloride |
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| ImageName2 = Space-filling model of acetyl chloride |
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| ImageFile3 = Acetyl chloride 25ml.jpg |
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| ImageFile3 = Acetyl chloride 25ml.jpg |
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| PIN = Acetyl chloride<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 796–797 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| IUPACName = Acetyl chloride |
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| OtherNames = Ethanoyl chloride |
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| SystematicName = Ethanoyl chloride |
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| OtherNames = Acyl chloride |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo = 75-36-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 37580 |
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| ChEBI = 37580 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = ClC(=O)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6127 |
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| ChemSpiderID = 6127 |
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| DrugBank = DB14623 |
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| EC_number = 200-865-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = QD15RNO45K |
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| UNII = QD15RNO45K |
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| Beilstein = 605303 |
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| Gmelin = 1611 |
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| PubChem = 6367 |
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| RTECS = AO6390000 |
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| UNNumber = 1717 |
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| InChI = 1/C2H3ClO/c1-2(3)4/h1H3 |
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| InChI = 1/C2H3ClO/c1-2(3)4/h1H3 |
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| InChIKey = WETWJCDKMRHUPV-UHFFFAOYAQ |
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| InChIKey = WETWJCDKMRHUPV-UHFFFAOYAQ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WETWJCDKMRHUPV-UHFFFAOYSA-N |
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| StdInChIKey = WETWJCDKMRHUPV-UHFFFAOYSA-N |
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| CASNo = 75-36-5 |
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| SMILES = ClC(=O)C |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = AO6390000 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = CH<sub>3</sub>COCl |
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| Formula = {{chem2|CH3COCl}} |
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| MolarMass = 78.49 g/mol |
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| MolarMass = 78.49 g/mol |
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| Appearance = colorless liquid |
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| Appearance = Colorless liquid |
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| Density = 1.104 g/ml, liquid |
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| Density = 1.104 g/ml, liquid |
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| Solubility = Reacts |
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| Solubility = Reacts with water |
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| MeltingPtC = -112 |
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| MeltingPtC = -112 |
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| BoilingPtC = 52 |
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| BoilingPtC = 52 |
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| MagSus = -38.9·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Viscosity = |
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| Viscosity = |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Dipole = 2.45 ] |
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| Dipole = 2.45 ] |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| GHSSignalWord = Danger |
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| EUClass = Flammable ('''F''')<br />Corrosive ('''C''') |
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| RPhrases = {{R11}} {{R14}} {{R34}} |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} |
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| HPhrases = {{H-phrases|225|302|314|335|412}} |
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| SPhrases = {{S1/2}} {{S9}} {{S16}} {{S26}} {{S45}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+312|301+330+331|303+361+353|304+340|305+351+338|310|312|321|330|363|370+378|403+233|403+235|405|501}} |
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| FlashPtC = 5 |
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| NFPA-H = 3 |
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| Autoignition = 390 °C |
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| NFPA-F = 3 |
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| ExploLimits = 7.3–19% |
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| NFPA-R = 2 |
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| NFPA-S= w |
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| FlashPtC = 4 |
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| AutoignitionPtC = 390 |
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| ExploLimits = 7.3–19% |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ]<br />] |
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| OtherFunction = ]<br />] |
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| OtherCpds = ]<br />]<br>] |
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| OtherCompounds = ]<br />]<br>] |
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}} |
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'''Acetyl chloride''' ({{chem2|CH3COCl}}) is an ] derived from ] ({{chem2|CH3COOH}}). It belongs to the class of ]s called ]s. It is a colorless, corrosive, volatile ]. Its formula is commonly abbreviated to AcCl. |
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==Synthesis== |
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On an industrial scale, the reaction of ] with ] produces a mixture of acetyl chloride and acetic acid:<ref>{{Ullmann |doi=10.1002/14356007.a01_045|title=Acetic Acid|year=2000|last1=Cheung|first1=Hosea|last2=Tanke|first2=Robin S.|last3=Torrence|first3=G. Paul|isbn=3527306730}}</ref> |
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:{{chem2 | (CH3CO)2O + HCl -> CH3COCl + CH3CO2H }} |
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===Laboratory routes=== |
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Acetyl chloride was first prepared in 1852 by French chemist ] by treating ] with ].<ref>See: |
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* Gerhardt, Charles (1852) (On anhydrous organic acids), ''Annalen der Chemie und Pharmacie'', '''83''' : 112–116. |
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* Gerhardt, Charles (1853) (Investigations into anhydrous organic acids), ''Annalen der Chemie und Pharmacie'', '''87''' : 57–84; see especially pp. 68–71.</ref> |
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Acetyl chloride is produced in the laboratory by the reaction of ] with chlorodehydrating agents such as ] ({{chem2|PCl3}}), ] ({{chem2|PCl5}}), ] ({{chem2|SO2Cl2}}), ], or ] ({{chem2|SOCl2}}). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions.<ref name="HdBook">{{cite book| title = Handbook of Reagents for Organic Synthesis, Activating Agents and Protective Groups| chapter = Acetyl chloride| author1 = Leo A. Paquette| publisher = John Wiley & Sons| year = 2005| isbn = 978-0-471-97927-2| page = 16}}</ref> |
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===Other methods=== |
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When heated, a mixture of ] and ] gives acetyl chloride.<ref name="HdBook" /> It can also be synthesized from the catalytic ] of ].<ref>{{cite patent|country=US|number=4352761|title=Production of acetyl chloride|pubdate=1982-10-05 |
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|inventor1-last=Erpenbach |inventor1-first=Heinz |
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|inventor2-last=Gehrmann |inventor2-first=Klaus |
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|inventor3-last=Lork |inventor3-first=Winfried |
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|inventor4-last=Pring |inventor4-first=Peter |
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|assign=] |
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}}</ref> |
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==Occurrence== |
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Acetyl chloride is not expected to exist in nature, because contact with ] would ] it into acetic acid and ]. In fact, if handled in open air it releases white "smoke" resulting from hydrolysis due to the moisture in the air. The smoke is actually small droplets of ] and ] formed by hydrolysis. |
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==Uses== |
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Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. Acetyl is an ] group having the formula {{chem2|\sC(\dO)\sCH3}}. For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see ]. Two major classes of acetylations include ] and the ]. |
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===Acetic acid esters and amide=== |
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Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the ] of ]s and ]s. One class of acetylation reactions are ], for example the reaction with ] to produce ] and ]: |
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:{{chem2 | CH3COCl + HO\sCH2\sCH3 -> CH3\sCOO\sCH2\sCH3 + HCl }} |
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Frequently such acylations are carried out in the presence of a base such as ], ], or ], which act as ]s to help promote the reaction and as ]s ] the resulting ]. Such reactions will often proceed via ]. |
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===Friedel-Crafts acetylations=== |
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A second major class of acetylation reactions are the ]s.<ref>Charles Merritt, Jr and Charles E. Braun "9-Acetylanthracene" Org. Synth. 1950, 30, 2. {{doi|10.15227/orgsyn.030.0001}}</ref> |
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==See also== |
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*] |
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*] |
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*] |
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*] |
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==References== |
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{{reflist}} |
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==External links== |
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*{{ICSC|0210}} |
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{{acetates}} |
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{{Authority control}} |
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] |
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] |
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] |