トリクロロ酢酸
- 関
- TCA、trichloroacetic acid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/22 16:50:01」(JST)
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Trichloroacetic acid
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|
|
| Names |
| IUPAC name
Trichloroacetic acid
|
| Identifiers |
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CAS Registry Number
|
76-03-9 N |
| ChEMBL |
ChEMBL14053 |
| Jmol-3D images |
Image |
| KEGG |
C11150 Y |
| PubChem |
6421 |
| RTECS number |
AJ7875000 |
|
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| Properties |
|
Chemical formula
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C2HCl3O2 |
| Molar mass |
163.38 g·mol−1 |
| Appearance |
Colorless to white, crystalline solid |
| Odor |
sharp, pungent [1] |
| Density |
1.63 g/cm³ |
| Melting point |
57 to 58 °C (135 to 136 °F; 330 to 331 K)[2] |
| Boiling point |
196 to 197 °C (385 to 387 °F; 469 to 470 K)[2] |
|
Solubility in water
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Soluble in 0.1 parts[2] |
| Vapor pressure |
1 mmHg (51.1°C)[1] |
| Acidity (pKa) |
0.66[3] |
| Structure |
|
Dipole moment
|
3.23 D |
| Hazards |
| EU classification |
Corrosive (C)
Dangerous for
the environment (N) |
| R-phrases |
R35, R50/53 |
| S-phrases |
(S1/2), S26, S36/37/39,
S45, S60, S61 |
| NFPA 704 |
|
| Lethal dose or concentration (LD, LC): |
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LD50 (Median dose)
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5000 mg/kg orally in rats[2] |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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none[1] |
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REL (Recommended)
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TWA 1 ppm (7 mg/m3)[1] |
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IDLH (Immediate danger
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N.D.[1] |
| Related compounds |
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Related chloroacetic acids
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Chloroacetic acid
Dichloroacetic acid |
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Related compounds
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Acetic acid
Trifluoroacetic acid
Tribromoacetic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| Y verify (what is: Y/N?) |
| Infobox references |
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Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.
Contents
- 1 Synthesis
- 2 Use
- 3 History
- 4 See also
- 5 References
- 6 External links
Synthesis
It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst.
- CH
3COOH + 3Cl
2 → CCl
3COOH +3HCl
Use
It is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. Solutions containing trichloroacetic acid as an ingredient are used for cosmetic treatments, such as chemical peels, tattoo removal, and the treatment of warts, including genital warts. It can kill normal cells as well. It is considered safe for use for this purpose during pregnancy.[4][5]
Salts and esters of trichloroacetic acid are called trichloroacetates.
Its sodium salt was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.[6][7][8][9][10]
History
The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1839 delivered a striking example to the slowly evolving theory of organic radicals and valences.[11] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[12]
See also
References
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards #0626National Institute for Occupational Safety and Health (NIOSH)
- ^ a b c d Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ^ Databog fysik kemi, F&K Forlaget 11. udgave 2009
- ^ "Trichloroacetic Acid or Bichloroacetic Acid for Genital Warts (Human Papillomavirus)". WebMD.
- ^ Wiley DJ, Douglas J, Beutner K, Cox T, Fife K, Moscicki AB, Fukumoto L (2002). "External genital warts: Diagnosis, treatment, and prevention". Clinical Infectious Diseases 35 (Suppl 2): S210–S224. doi:10.1086/342109. PMID 12353208.
- ^ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
- ^ G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Weeds 2(4) Oct. 1953: 271-279
- ^ OECD Trichloroacetic Acid CAS N°: 76-03-9 Accessed June 20, 2014
- ^ EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014
- ^ PAN Trichloroacetic acid, sodium salt
- ^ Dumas (1839). "Trichloroacetic acid". Annalen der Pharmacie 32: 101–119. doi:10.1002/jlac.18390320109.
- ^ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society 66: 287–308. JSTOR 3301070.
External links
- International Chemical Safety Card 0586
- CDC - NIOSH Pocket Guide to Chemical Hazards
English Journal
- Highly Active, Thermally Stable, Ethylene-Polymerisation Pre-Catalysts Based on Niobium/TantalumImine Systems.
- Redshaw C, Walton M, Clowes L, Hughes DL, Fuller AM, Chao Y, Walton A, Sumerin V, Elo P, Soshnikov I, Zhao W, Sun WH.SourceDepartment of Chemistry, University of Hull, Hull, HU6 7RX (UK). c.redshaw@hull.ac.uk.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2013 May 16. doi: 10.1002/chem.201300453. [Epub ahead of print]
- The reactions of MCl5 or MOCl3 with imidazole-based pro-ligand L1 H, 3,5-tBu2 -2-OH-C6 H2 -(4,5-Ph2 -1H-)imidazole, or oxazole-based ligand L2 H, 3,5-tBu2 -2-OH-C6 H2 (1H-phenanthro[9,10-d])oxazole, following work-up, afforded octahedral complexes [MX(L1, 2 )], where MX=NbCl4 (L1 , 1 a; L2 , 2�
- PMID 23681561
- Metabolomics reveals trichloroacetate as a major contributor to trichloroethylene-induced metabolic alterations in mouse urine and serum.
- Fang ZZ, Krausz KW, Tanaka N, Li F, Qu A, Idle JR, Gonzalez FJ.SourceLaboratory of Metabolism, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Building 37, Room 3106, Bethesda, MD, 20892, USA.
- Archives of toxicology.Arch Toxicol.2013 Apr 11. [Epub ahead of print]
- Trichloroethylene (TCE)-induced liver toxicity and carcinogenesis is believed to be mediated in part by activation of the peroxisome proliferator-activated receptor α (PPARα). However, the contribution of the two TCE metabolites, dichloroacetate (DCA) and trichloroacetate (TCA) to the toxicity of
- PMID 23575800
- The induction of phagocytic activation by mixtures of the water chlorination by-products, dichloroacetate- and trichloroacetate, in mice after subchronic exposure.
- Hassoun EA, Cearfoss J, Musser B, Krispinsky S, Al-Hassan N, Liu MC.SourceCollege of Pharmacy and Pharmaceutical Sciences, The University of Toledo, Toledo, OH 43614-2598, USA. ezdihar.hassoun@utoledo.edu
- Journal of biochemical and molecular toxicology.J Biochem Mol Toxicol.2013 Apr;27(4):237-42. doi: 10.1002/jbt.21476. Epub 2013 Feb 21.
- In this study, groups of B6C3F1 male mice were treated with dichloroacetate (DCA), trichloroacetate (TCA), and mixtures of the compounds (Mix I, II, and III) daily by gavage, for 13 weeks. The tested doses were 7.5, 15, and 30 mg DCA/kg/day and 12.5, 25, and 50 mg TCA/kg/day. The DCA: TCA ratios in
- PMID 23436740
Japanese Journal
- 御厨 正博
- Bulletin of Japan Society of Coordination Chemistry 52, 17-28, 2008
- … By using copper(II) trichloroacetate, a chain molecule consisting of alternated arrangement of tetranuclear cubane and pyrazine was isolated. …
- NAID 130002145054
- キラル銀錯体を用いる触媒的不斉炭素-炭素結合形成反応
- 柳澤 章,山本 尚
- 有機合成化学協会誌 63(9), 888-898, 2005
- … Later, we developed an alternative BINAP·AgOTf-catalyzed asymmetric aldol reaction of an alkenyl trichloroacetate employing a catalytic amount of trialkyltin methoxide. …
- NAID 130000928547
- Potentiometric Responses of Expanded Porphyrin Incorporated Liquid Membrane Electrodes toward a Series of Inorganic and Organic Anions
- Lin Xiao Ming,Umezawa Kayoko,Tohda Koji [他],FURUTA Hiroyuki,SESSLER Jonathan L.,UMEZAWA Yoshio
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 14(1), 99-108, 1998-02-10
- NAID 10002414237
Related Links
- forum Join the Word of the Day Mailing List For webmasters TheFreeDictionary Google Bing? Word / Article Starts with Ends with Text ... trichloroacetate a relatively nontoxic herbicide.
- Structure, properties, spectra, suppliers and links for: trichloroacetate. ... Predicted data is generated using the US Environmental Protection Agency’s EPISuite , for more information see their website. Log Octanol-Water Partition ...
Related Pictures
★リンクテーブル★
[★]
- 英
- trichloroacetic acid, trichloroacetate, TCA
- 関
- トリクロロエチレン中毒
- CCl3-COOH
[★]
トリクロロ酢酸
- 関
- TCA、trichloroacetate