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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/15 08:00:23」(JST)

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Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF₃CO₂H. It is a colorless liquid with a sharp odor similar to vinegar, but stronger in acidity. TFA is an analogue of acetic acid with the three hydrogen atoms replaced by three fluorine atoms. The acidity of TFA is approximately 34,000 times stronger^[2] than that of acetic acid due to the electronegativity of the trifluoromethyl group. TFA is widely used in organic chemistry for various purposes.

Synthesis

TFA is prepared industrially by the electrofluorination of acetyl chloride and acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride:^[3]

CH
3COCl + 4 HF → CF
3COF + 3 H
2 + HCl

CF
3COF + H
2O → CF
3COOH + HF

Where desired, this compound may be dried by addition of trifluoroacetic anhydride.^[4]

An older route to TFA proceeds via the oxidation of 1,1,1-trifluoro-2,3,3-trichloropropene with potassium permanganate. The trifluorotrichloropropene can be prepared by Swarts fluorination of hexachloropropene.

TFA occurs naturally in sea water, but only in small concentrations (<200 ng/L).^[5]^[6]

Uses

TFA is the precursor to many other fluorinated compounds such as trifluoroacetic anhydride and 2,2,2-trifluoroethanol.^[3] It is a reagent used in organic synthesis because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength as an acid.^[7] TFA is also less oxidizing than sulfuric acid but more readily available in anhydrous form than many other acids. One complication to its use is that TFA forms an azeotrope with water (b. p. 105 °C).

TFA is popularly used as a strong acid in peptide synthesis and other organic synthesis to remove the t-butoxycarbonyl protecting group.^[8]^[9]

At a low concentration, TFA is used as an ion pairing agent in liquid chromatography (HPLC) of organic compounds, particularly peptides and small proteins. TFA is a versatile solvent for NMR spectroscopy (for materials stable in acid). It is also used as a calibrant in mass spectrometry.^[10]

TFA is used to produce trifluoroacetate salts.^[11]

Safety

Trifluoroacetic acid is a corrosive acid but it does not pose the hazards associated with hydrofluoric acid because the carbon-fluorine bond is not labile. Toxic.

References

^ Ref 1 in Milne, J. B.; Parker, T. J. (1981). "Dissociation constant of aqueous trifluoroacetic acid by cryoscopy and conductivity". Journal of Solution Chemistry 10 (7): 479. doi:10.1007/BF00652082.
^ Note: Calculated from Ka ratio of TFA and acetic acid
^ ^a ^b G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, B. McKusick (2005), "Fluorine Compounds, Organic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a11_349
^ Wilfred L.F. Armarego and Christina Li Lin Chai. "Chapter 4 - Purification of Organic Chemicals". Purification of Laboratory Chemicals (6th Ed. ed.). doi:10.1016/B978-1-85617-567-8.50012-3.
^ "Trifluoroacetate in ocean waters". Environ. Sci. Technol. 36 (1): 12–5. January 2002. Bibcode:2002EnST...36...12P. doi:10.1021/es0221659. PMID 11811478.
^ "Trifluoroacetate profiles in the Arctic, Atlantic, and Pacific Oceans". Environ. Sci. Technol. 39 (17): 6555–60. September 2005. Bibcode:2005EnST...39.6555S. doi:10.1021/es047975u. PMID 16190212.
^ Eidman, K. F.; Nichols, P. J. (2004). "Trifluoroacetic Acid". In L. Paquette. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289.
^ Lundt, Behrend F.; Johansen, Nils L.; Vølund, Aage; Markussen, Jan (1978). "Removal of t-Butyl and t-Butoxycarbonyl Protecting Groups with Trifluoroacetic acid". International Journal of Peptide and Protein Research 12 (5): 258–268. doi:10.1111/j.1399-3011.1978.tb02896.x. PMID 744685.
^ Andrew B. Hughes. "1. Protection Reactions". In Vommina V. Sureshbabu, Narasimhamurthy Narendra. Amino Acids, Peptides and Proteins in Organic Chemistry: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis 4. doi:10.1002/9783527631827.ch1.
^ Stout, Steven J.; Dacunha, Adrian R. (1989). "Tuning and calibration in thermospray liquid chromatography/mass spectrometry using trifluoroacetic acid cluster ions". Analytical Chemistry 61 (18): 2126. doi:10.1021/ac00193a027.
^ O. Castano, A. Cavallaro, A. Palau, J. C. Gonzalez, M. Rossell, T. Puig, F. Sandiumenge, N. Mestres, S. Pinol, A. Pomar, and X. Obradors (2003). "High quality YBa₂Cu₃O₇ thin films grown by trifluoroacetates metal-organic deposition". Superconductor Science and Technology 16 (1): 45–53. Bibcode:2003SuScT..16...45C. doi:10.1088/0953-2048/16/1/309.

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Seo U Min,Zhao Bing Tian,Kim Won Il,Seo Eun Kyoung,Lee Jae Hyun,Min Byung Sun,Shin Beom Soo,Son Jong Keun,Woo Mi Hee
Chemical and Pharmaceutical Bulletin 63(7), 546-553, 2015
… To establish a standard for quality control as well as the reliable identification of Farfarae Flos, the contents of five standards, rutin (1), isoquercetin (2), 3,5-dicaffeoylquinic acid (3), tussilagone (4), and tussilagonone (5), were determined by quantitative high-performance liquid chromatography (HPLC)/photodiode array (PDA) analysis. …
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Related Pictures

★リンクテーブル★

リンク元	「TFA」「trifluoroacetate」「トリフルオロ酢酸」

「TFA」

Trifluoroacetic acid
Names
	IUPAC name 2,2,2-Trifluoroethanoic acid
	Other names Perfluoroacetic acid; Trifluoroethanoic acid; TFA
Identifiers
CAS Registry Number	76-05-1
ChEBI	CHEBI:45892
ChEMBL	ChEMBL506259
ChemSpider	10239201
	InChI InChI=1S/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7) ; Key: DTQVDTLACAAQTR-UHFFFAOYSA-N ; InChI=1/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7); Key: DTQVDTLACAAQTR-UHFFFAOYAP ;
Jmol-3D images	Image
PubChem	6422
RTECS number	AJ9625000
	SMILES FC(F)(F)C(=O)O ;
UNII	E5R8Z4G708
Properties
Chemical formula	C2HF3O2
Molar mass	114.02 g/mol
Appearance	colorless liquid
Density	1.489 g/cm3, 20 °C
Melting point	−15.4 °C (4.3 °F; 257.8 K)
Boiling point	72.4 °C (162.3 °F; 345.5 K)
Solubility in water	miscible
Acidity (pKa)	0.23
Hazards
MSDS	External MSDS
Main hazards	Highly corrosive
R-phrases	R20 R35 R52/53
S-phrases	S9 S26 S27 S28 S45 S61
NFPA 704	1 3 1
Flash point	−3 °C (27 °F; 270 K)
Related compounds
Related perfluorinated acids	Perfluorooctanoic acid; Perfluorononanoic acid
Related compounds	Acetic acid; Trichloroacetic acid
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references