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{{chembox |
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{{chembox |
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| verifiedrevid = 277558827 |
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| verifiedrevid = 374753871 |
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| Name = |
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|ImageFile=Trifluoroacetic anhydride.svg |
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| ImageFile = Trifluoroacetic anhydride.svg |
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|ImageSize= |
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| ImageSize = |
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|IUPACName=trifluoroacetic anhydride |
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| ImageAlt = Skeletal formula |
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|OtherNames= |
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| ImageFile1 = Trifluoroacetic-anhydride-3D-balls.png |
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|Section1={{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model |
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| CASNo_Ref = {{cascite}} |
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| PIN = Trifluoroacetic anhydride |
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| SystematicName = |
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| OtherNames = {{Unbulleted list|2,2,2-Trifluoroacetic anhydride|TFAA}} |
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| IUPACName = |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=407-25-0 |
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| CASNo=407-25-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=9845 |
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| UNII = 5ENA87IZHT |
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| SMILES=C(=O)(C(F)(F)F)OC(=O)C(F)(F)F |
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| PubChem=9845 |
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| ChemSpiderID = 21106178 |
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| EC_number = 206-982-9 |
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| SMILES=C(=O)(C(F)(F)F)OC(=O)C(F)(F)F |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = QAEDZJGFFMLHHQ-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C = 4 | F = 6 | O = 3 |
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| C=4 | F=6 | O=3 |
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| Appearance= |
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| Appearance= colorless liquid |
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| Density=1.487 g/mL |
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| Density= 1.511 g/mL (20°C) |
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| MeltingPtC = -65 |
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| MeltingPtC = -65 |
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| BoilingPtC = 40 |
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| BoilingPtC = 40 |
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| Solubility= |
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| Solubility= reacts |
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| SolubleOther = soluble in ], ], ], ], ], ] |
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|Section3={{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| ExternalSDS = |
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| EUClass = Harmful (Xn); Corrosive (C) |
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| GHSPictograms = {{GHS05}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich|supelco|id=33165u|name=Trifluoroacetic Anhydride|accessdate=2020-06-08}}</ref> |
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| GHSSignalWord = Danger |
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| FlashPt= |
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| HPhrases = {{H-phrases|314|332}}<ref name="sigma"/> |
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| Autoignition= |
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| PPhrases = {{P-phrases|280|305+351+338|310}} <ref name="sigma"/> |
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'''Trifluoroacetic anhydride''' ('''TFAA''') is the ] of ]. It is the perfluorinated derivative of ]. |
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'''Trifluoroacetic anhydride (TFAA)''' is the ] of ]. In particular, trifluoroacetic anhydride is the perfluorinated derivative of ]. Like many acid anhydrides, it may be used to introduce the corresponding trifluoroacetyl group. The corresponding ], is a gas, making it inconvenient to work with. Trifluoroacetic anhydride is the recommended ] for trifluoroacetic acid.<ref>{{cite book |author=Chai, Christina Li Lin; Armarego, W. L. F. |title=Purification of laboratory chemicals |publisher=Butterworth-Heinemann |location=Oxford |year=2003 |pages=376 |isbn=0-7506-7571-3 | url = http://books.google.com/books?id=SYzm1tx2z3QC&pg=PA376 | format = ] excerpt}}</ref> |
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==Preparation== |
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==Preparation== |
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Trifluoroacetic anhydride may be prepared from trifluoroacetic acid by dehydrating with excess α-halogenated ]s. For example, with ]:<ref>{{Cite patent |US|4595541}}</ref> |
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Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with ].<ref name=":0">{{Cite journal|last=Tedder|first=J. M.|date=1955|title=The Use of Trifluoroacetic Anhydride and Related Compounds in Organic Synthesis|journal=]|volume=55|issue=5|pages=787–827|doi=10.1021/cr50005a001}}</ref> The dehydration might also be carried out with excess α-halogenated ]s. For example, with ]:<ref>{{Cite patent|country=US|number=4595541|pubdate=1986-06-17|title=Process for the preparation of trifluoroacetic anhydride|assign1=]|inventor1-last=Amiet|inventor1-first=Louis|inventor2-last=Disdier|inventor2-first=Camille}}</ref> |
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: 2 CF<sub>3</sub>COOH + Cl<sub>2</sub>CHCOCl → (CF<sub>3</sub>CO)<sub>2</sub>O + Cl<sub>2</sub>CHCOOH + HCl |
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: 2 CF<sub>3</sub>COOH + Cl<sub>2</sub>CHCOCl → (CF<sub>3</sub>CO)<sub>2</sub>O + Cl<sub>2</sub>CHCOOH + HCl |
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== Uses == |
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Trifluoroacetic anhydride has various uses in ]. |
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It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding ], ], which is a gas. |
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It can be used to promote reactions of carboxylic acids, including ] and acylation of other unsaturated compounds. Other ] reactions can also be promoted with trifluoroacetic anhydride, including nitration, sulfonation and nitrosylation.<ref name=":0" /> |
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Similar to ], trifluoroacetic anhydride can be used as a dehydrating agent and as an activator for the ].<ref name="encyclopedia">{{Cite book|last1=Sweeney|first1=Joseph|title=Encyclopedia of Reagents for Organic Synthesis|last2=Perkins|first2=Gemma|last3=DiMauro|first3=Erin F.|last4=Hodous|first4=Brian L.|publisher=John Wiley & Sons|year=2005|isbn=978-0-470-84289-8|chapter=Trifluoroacetic Anhydride|doi=10.1002/047084289X.rt237.pub2}}</ref> |
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It can be used in place of ] in the ], allowing temperatures up to −30 °C.<ref>{{cite journal|last1=Omura|first1=Kanji|last2=Sharma|first2=Ashok K.|last3=Swern|first3=Daniel|title=Dimethyl Sulfoxide-Trifluoroacetic Anhydride. New Reagent for Oxidation of Alcohols to Carbonyls|journal=]|date=1976 |volume=41|issue=6|pages=957–962|doi=10.1021/jo00868a012}}</ref> |
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With ], it reduces ]s to ].<ref name="encyclopedia"/> |
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Trifluoroacetic anhydride is the recommended ] for trifluoroacetic acid.<ref>{{cite book|author1=Chai, Christina Li Lin|url=https://books.google.com/books?id=SYzm1tx2z3QC&pg=PA376|title=Purification of laboratory chemicals|author2=Armarego, W. L. F.|publisher=Butterworth-Heinemann|year=2003|isbn=0-7506-7571-3|location=Oxford|pages=376|format=] excerpt}}</ref> |
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==References== |
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==References== |
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