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407-25-0 molecular structure
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trifluoroacetyl 2,2,2-trifluoroacetate

ChemBase ID: 99501
Molecular Formular: C4F6O3
Molecular Mass: 210.0314192
Monoisotopic Mass: 209.97516318
SMILES and InChIs

SMILES:
FC(F)(F)C(=O)OC(=O)C(F)(F)F
Canonical SMILES:
O=C(C(F)(F)F)OC(=O)C(F)(F)F
InChI:
InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
InChIKey:
QAEDZJGFFMLHHQ-UHFFFAOYSA-N

Cite this record

CBID:99501 http://www.chembase.cn/molecule-99501.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
trifluoroacetyl 2,2,2-trifluoroacetate
IUPAC Traditional name
trifluoroacetic anhydride
Synonyms
Trifluoroacetic anhydride 99%
2,2,2-Trifluoroacetic anhydride
TFAA
Trifluoroacetic anhydride
TRIFLUOROACETIC ANHYDRIDE
三氟乙酸酐
CAS Number
407-25-0
EC Number
206-982-9
MDL Number
MFCD00000416
Beilstein Number
746197
PubChem SID
162085766
24889536
24846727
PubChem CID
9845
Wikipedia Title
Trifluoroacetic_anhydride

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.9521378  LogD (pH = 7.4) 1.9521378 
Log P 1.9521378  Molar Refractivity 24.1024 cm3
Polarizability 9.386645 Å3 Polar Surface Area 43.37 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
clear, colorless liquid expand Show data source
Melting Point
-63°C expand Show data source
-65 °C(lit.) expand Show data source
-65°C expand Show data source
-65°C expand Show data source
Boiling Point
39- 40°C expand Show data source
39°C expand Show data source
39.5-40 °C(lit.) expand Show data source
39-40°C expand Show data source
39-40°C expand Show data source
40°C expand Show data source
Density
1.487 g/ml expand Show data source
1.487 g/mL expand Show data source
1.498 g/ml expand Show data source
1.503 expand Show data source
1.511 expand Show data source
1.511 g/mL at 20 °C(lit.) expand Show data source
Refractive Index
1.269 expand Show data source
1.2690 expand Show data source
n20/D 1.3(lit.) expand Show data source
Vapor Pressure
6.28 psi ( 20 °C) expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
Corrosive/Harmful/Moisture Sensitive/Store under Argon expand Show data source
Moisture Sensitive expand Show data source
RTECS
AJ9800000 expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
UN Number
1760 expand Show data source
3265 expand Show data source
UN3265 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
1 expand Show data source
I expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
14-20-35-52/53 expand Show data source
35 expand Show data source
R:14-34 expand Show data source
R:35 expand Show data source
Safety Statements
20-26-36/37/39-45-60 expand Show data source
26-36/37/39-43-45-61 expand Show data source
S:26-27/28-36/37/39-46-64 expand Show data source
S:27/28-30-36/37/39-45 expand Show data source
EU Classification
C9 expand Show data source
EU Hazard Identification Number
8B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H314-H318 expand Show data source
H314-H332 expand Show data source
H314-H332-H412 expand Show data source
GHS Precautionary statements
P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A expand Show data source
P273-P280-P305 + P351 + P338-P310 expand Show data source
P280-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US) expand Show data source
RID/ADR
UN 3265 8/PG 1 expand Show data source
Supplemental Hazard Statements
Reacts violently with water. expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
~99% expand Show data source
≥99% expand Show data source
≥99.0% (GC) expand Show data source
95+% expand Show data source
97% expand Show data source
99+% expand Show data source
Grade
for GC derivatization expand Show data source
puriss. p.a. expand Show data source
purum expand Show data source
ReagentPlus® expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Derivatization reagent for
Acetylations expand Show data source
Acylations expand Show data source
Esterifications expand Show data source
Linear Formula
(CF3CO)2O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Apollo Scientific Apollo Scientific Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02190285 external link
Clear, colorless liquid
Purity: ~99%
1 ml = approx. 1.49 g
MP Biomedicals - 05219309 external link
MP Biomedicals Rare Chemical collection
Apollo Scientific Ltd - PC7170 external link
Useful trifluoroacetylating agent for the protectionof alcohols & amines: Helv.Chim.Acta., 37, 443 (1954)Ask for a bulk quote. Packaged in Safebreak bottles
Sigma Aldrich - 106232 external link
Packaging
10×1 g in ampule
3 kg in glass bottle
25 kg in comp drum
25, 100, 500 g in glass bottle
Application
For the preparation of N- and O-trifluoroacetyl derivatives of a wide range of biologically active compounds for GC analysis. Also used in the oxidation of aldehydes to acids, esters, or amides.1
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 91719 external link
Other Notes
For the protection of prim. and sec. amines; derivatives are more volatile1
Sigma Aldrich - 91720 external link
Other Notes
Powerful activator in the DMSO oxidation of alcohols to carbonyl compounds1,2

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Trifluoroacetylating agent for protection of alcohols and amines: Helv. Chim. Acta., 37, 443 (1954); Tetrahedron,43, 5583 (1987); Tetrahedron Lett., 28, 4737 (1987), useful, e.g. as volatile derivatives in GC: J. Chromat., 43, 129 (1969); 61, 225 (1971); 93, 223, 447 (1974); D. R. Knapp, Handbook of Analytical Derivatisation Reactions, Wiley, N.Y. (1979); Handbook of Derivatives for Chromatography, 2nd ed., K. Blau and J. M. Halket, Eds., Wiley, Chichester (1993).
  • • Trifluoroacetyl esters are rapidly hydrolyzed at pH 7: Tetrahedron Lett., 1039 (1963). Trifluoroacetamides are also readily hydrolyzed e.g. by mild base; selective cleavage of a trifluoroacetamide can be achieved in the presence of a methyl ester: J. Org. Chem., 54, 2498 (1989). For the racemization-free removal of the N-trifluoroacetyl group from peptides by NaBH4, see: Chem. Ber., 103, 2437 (1970).
  • • In pyridine and dichloromethane or ether, converts acid chlorides to trifluoromethyl ketones in good yields via a trifluoroacyl ketene intermediate: Tetrahedron, 51, 2573 (1995). The method has been extended to the synthesis of a range of trifluoromethylated heterocycles: Tetrahedron, 51, 2585 (1995):
  • • In pyridine, dehydrates carboxamides or aldoximes to nitriles: Tetrahedron Lett., 1813 (1977); Synthesis, 56, (1979). With triethylamine, effects the dehydration of aldols to enones, where other methods are less successful: Org. Synth. Coll., 8, 210 (1993).
  • • For the ɑ-trifluoroacetylation of a phosphonium salt in a route to perfluoroalkyl acetylenes, see: Org. Synth. Coll., 9, 436 (1998). For reaction scheme, see (Ethoxycarbonylmethyl)triphenylphosphonium bromide, A16347.
  • • Alternative to Oxalyl chloride, A18012, for activation of Dimethyl sulfoxide, A13280 in the low temperature Swern oxidation of alcohols to aldehydes or ketones: J. Org. Chem., 41,957 (1976); Tetrahedron, 34, 1651 (1978). This reagent often gives cleaner reactions and improved yields, e.g. in the synthesis of a sensitive 1,2-dione from the diol: J. Org. Chem., 52, 4851 (1987).
  • • Mild conversion of aryl halides to aryl trifluoromethyl ketones via Pd catalyzed stannylation: Synlett, 165 (1995).
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PATENTS

PATENTS

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