Trifluoroacetic anhydride
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Basic information
- CAS
407-25-0- Standard SMILES
O=C(OC(=O)C(F)(F)F)C(F)(F)F- InChIKey
QAEDZJGFFMLHHQ-UHFFFAOYSA-N- Molecular formula
- C4F6O3
- Average molar mass
- 210.03 g/mol
- Monoisotopic mass
- 209.97516318
Names & identifiers
- Preferred name
- Trifluoroacetic anhydride
- IUPAC
- (2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate
- English name
- Trifluoroacetic anhydride
- Molecular formula
- C4F6O3
- Molecular weight
- 210.03
Names & synonyms
TRIFLUOROACETIC ANHYDRIDE407-25-0Trifluoroacetic acid anhydrideBis(trifluoroacetic) anhydridePerfluoroacetic anhydrideTrifluoroacetyl anhydrideHexafluoroacetic anhydrideAnhydrid kyseliny trifluoroctove5ENA87IZHTNSC-96965DTXSID90861920RefChem:899576
Show more names
trifluoroaceticTRIFLUORACETIC ANHYDRIDETIFLUOROACETIC ANHYDRIDETrifluoroacetic anhyTrifluoroacetic anhydride 10g [407-25-0]uoroacetic anhydridetrimethylamine (TMA)
DTXCID90810771206-982-9TFAA2,2,2-trifluoroacetic anhydrideAcetic acid, trifluoro-, anhydridetrifluoro acetic anhydride(2,2,2-trifluoroacetyl) 2,2,2-trifluoroacetate2,2,2-trifluoroacetyl 2,2,2-trifluoroacetate
Database identifiers
- CAS
407-25-0- PubChem CID
- 9845
- DTXSID
DTXSID90861920- UNII
- 5ENA87IZHT
- EC Number
- 206-982-9
- Nikkaji
- J5.723A
Properties
Computed structural propertiesFilling in
- XLogP
- 2.1
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 201
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Acid Anhydrides, Other
PFAS
PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds
SpringerMaterials PropertiesSchoenflies notation
Density1.49 @25 °C
Boiling Point39.5 °C @760 [mm Hg]
Vapor Pressure41.2 [mmHg]
Physical Description
Liquid
Colorless liquid; [MSDSonline]
Physicochemical properties
- Melting point
- -65 °C · -65 °C (lit.)
- Boiling point
- 39.5 · 39.5-40 °C (lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P203, P260, P261, P264, P264+P265, P271, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 114 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Acetic acid, trifluoro-, anhydride
Acetic acid, 2,2,2-trifluoro-, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2,2,2-trifluoro-, 1,1'-anhydride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 29-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/10848
Trifluoroacetic anhydride: HSNO Approval: HSR004742 Approved with controls
Hazards SummaryCorrosive to skin; [eChemPortal: ERMA] Reacts with water; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]
Hazard Classes and CategoriesSkin Corr. 1A (100%)
Safety & protection
Protective Action Criteria (PAC)
0.60 [mg/m3]
6.6 [mg/m3]
Chemistry & industry
Uses & manufacturing
U.S. Production2023: <50,000 lb
Industry UsesIntermediate
General Manufacturing Information
Miscellaneous Manufacturing
Acetic acid, 2,2,2-trifluoro-, 1,1'-anhydride: ACTIVE
Applications
DescriptionTrifluoroacetic acid anhydride (TFAA), a perfluoroacylated acylation reagent, forms stable, volatile derivatives with alcohols, amines, and phenols.
UsesUsed as analytical reagents, solvents, catalysts, dehydration condensing agent, protection agent of trifluoroacetylation of carboxyl and amino; used as Intermediate of fluorine fine chemicals, pharmaceutical, agrochemical.
UsesTrifluoroacetic anhydride is used for the introduction of trifluoroacetyl group in organic synthesis. It is involved in the preparation of N- and O-trifluoroacetyl derivatives of a wide range of biologically active compounds for gas chromatography analysis. It plays an important role as desiccant for trifluoroacetic acid. It is also used in the oxidation of aldehydes to acids, esters, amides as well as in the protection of alcohols and amines. In addition, it is used as analytical reagents, solvents and dehydration condensing agent. It serves as an intermediate of fluorine fine chemicals, pharmaceuticals and agrochemicals.
Preparation methods
PreparationTrifluoroacetic anhydride is prepared by reaction of trifluoroacetyl chloride with an alkali metal or alkaline-earth metal salt of trifluoroacetic acid at approximately 50° C.
Upstream & downstream products
Upstream raw materials
Related reactions
2,516 records
Compound notes
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