Trifluoroacetic anhydride: Difference between revisions

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	\|IUPACName=trifluoroacetic anhydride
			\| ImageAlt = Skeletal formula
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			\| ImageFile1 = Trifluoroacetic-anhydride-3D-balls.png
⚫	\|Section1={{Chembox Identifiers
			\| ImageAlt1 = Ball-and-stick model
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			\| PIN = Trifluoroacetic anhydride
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			\| OtherNames = {{Unbulleted list\|2,2,2-Trifluoroacetic anhydride\|TFAA}}
			\| IUPACName =
		⚫	\| Section1 = {{Chembox Identifiers
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		⚫	\| PubChem=9845
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			\| EC_number = 206-982-9
		⚫	\| SMILES=C(=O)(C(F)(F)F)OC(=O)C(F)(F)F
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			\| StdInChIKey = QAEDZJGFFMLHHQ-UHFFFAOYSA-N
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	\| Appearance=		\| Appearance= colorless liquid
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	\| MeltingPtC = -65		\| MeltingPtC = -65
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			\| SolubleOther = soluble in ], ], ], ], ], ]
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	\| EUClass = Harmful (Xn); Corrosive (C)
			\| GHSPictograms = {{GHS05}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich\|supelco\|id=33165u\|name=Trifluoroacetic Anhydride\|accessdate=2020-06-08}}</ref>
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			'''Trifluoroacetic anhydride''' ('''TFAA''') is the ] of ]. It is the perfluorinated derivative of ].
	'''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>

	==Preparation==		==Preparation==
	Trifluoroacetic anhydride ~~may~~ be prepared ~~from~~ trifluoroacetic acid by ~~dehydrating~~ with excess ~~α~~-halogenated ]s. For example, with ]:<ref>{{Cite patent \|US\|4595541}}</ref>		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>

	: 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		: 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

			== Uses ==
			Trifluoroacetic anhydride has various uses in ].

			It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding ], ], which is a gas.

			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" />

			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>

			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>

			With ], it reduces ]s to ].<ref name="encyclopedia"/>

			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>

	==References==		==References==
	<references/>		<references/>

	]		]
	]		]

	]
	]

Latest revision as of 13:41, 26 August 2024

Trifluoroacetic anhydride
Names


Preferred IUPAC name Trifluoroacetic anhydride
Other names 2,2,2-Trifluoroacetic anhydride TFAA
Identifiers
CAS Number	407-25-0
3D model (JSmol)	Interactive image
ChemSpider	21106178
ECHA InfoCard	100.006.349
EC Number	206-982-9
PubChem CID	9845
UNII	5ENA87IZHT
CompTox Dashboard (EPA)	DTXSID40893892 DTXSID90861920, DTXSID40893892
InChI InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10Key: QAEDZJGFFMLHHQ-UHFFFAOYSA-N
SMILES C(=O)(C(F)(F)F)OC(=O)C(F)(F)F
Properties
Chemical formula	C₄F₆O₃
Molar mass	210.031 g·mol
Appearance	colorless liquid
Density	1.511 g/mL (20°C)
Melting point	−65 °C (−85 °F; 208 K)
Boiling point	40 °C (104 °F; 313 K)
Solubility in water	reacts
Solubility	soluble in benzene, dichloromethane, ether, DMF, THF, acetonitrile
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H332
Precautionary statements	P280, P305+P351+P338, P310
Safety data sheet (SDS)	Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride.

Preparation

Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with phosphorus pentoxide. The dehydration might also be carried out with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride:

2 CF₃COOH + Cl₂CHCOCl → (CF₃CO)₂O + Cl₂CHCOOH + HCl

Uses

Trifluoroacetic anhydride has various uses in organic synthesis.

It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding acyl chloride, trifluoroacetyl chloride, which is a gas.

It can be used to promote reactions of carboxylic acids, including Friedel-Crafts acylation and acylation of other unsaturated compounds. Other electrophilic aromatic substitution reactions can also be promoted with trifluoroacetic anhydride, including nitration, sulfonation and nitrosylation.

Similar to acetic anhydride, trifluoroacetic anhydride can be used as a dehydrating agent and as an activator for the Pummerer rearrangement.

It can be used in place of oxalyl chloride in the Swern oxidation, allowing temperatures up to −30 °C.

With sodium iodide, it reduces sulfoxides to sulfides.

Trifluoroacetic anhydride is the recommended desiccant for trifluoroacetic acid.

References

^ Sigma-Aldrich Co., Trifluoroacetic Anhydride. Retrieved on 2020-06-08.
^ Tedder, J. M. (1955). "The Use of Trifluoroacetic Anhydride and Related Compounds in Organic Synthesis". Chem. Rev. 55 (5): 787–827. doi:10.1021/cr50005a001.
US 4595541, Amiet, Louis & Disdier, Camille, "Process for the preparation of trifluoroacetic anhydride", published 1986-06-17, assigned to Rhone Poulenc Specialites Chimiques
^ Sweeney, Joseph; Perkins, Gemma; DiMauro, Erin F.; Hodous, Brian L. (2005). "Trifluoroacetic Anhydride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rt237.pub2. ISBN 978-0-470-84289-8.
Omura, Kanji; Sharma, Ashok K.; Swern, Daniel (1976). "Dimethyl Sulfoxide-Trifluoroacetic Anhydride. New Reagent for Oxidation of Alcohols to Carbonyls". J. Org. Chem. 41 (6): 957–962. doi:10.1021/jo00868a012.
Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals (Google Books excerpt). Oxford: Butterworth-Heinemann. p. 376. ISBN 0-7506-7571-3.

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