Trichloroacetic acid
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Names | |||
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Preferred IUPAC name
Trichloroacetic acid | |||
Identifiers | |||
3D model (
JSmol ) |
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970119 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.000.844 | ||
2842 | |||
KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
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] | ||
1000 g/100 mL[2] | |||
Vapor pressure | 1 mmHg (51.1 °C)[1] | ||
Acidity (pKa) | 0.66[3] | ||
−73.0·10−6 cm3/mol | |||
Structure | |||
3.23 D | |||
Hazards | |||
GHS labelling: | |||
Danger | |||
H314, H410 | |||
P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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5000 mg/kg orally in rats[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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None[1] | ||
REL (Recommended)
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TWA 1 ppm (7 mg/m3)[1] | ||
IDLH (Immediate danger) |
N.D.[1] | ||
Related compounds | |||
Related chloroacetic acids
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Chloroacetic acid Dichloroacetic acid | ||
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).
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Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of
of trichloroacetic acid are called trichloroacetates.Synthesis
Trichloroacetic acid was discovered by Jean-Baptiste Dumas in 1830.[4]
It is prepared by the reaction of chlorine with
- CH
3COOH + 3 Cl
2 → CCl
3COOH + 3 HCl
Another route to trichloroacetic acid is the oxidation of
Use
It is widely used in
The sodium salt (sodium trichloroacetate) was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.[7][8][9][10]
Environmental and health concerns
According to the European Chemicals Agency, "This substance causes severe skin burns and eye damage, is very toxic to aquatic life and has long lasting toxic effects."[11]
History
The discovery of trichloroacetic acid by
Popular culture
In the 1958 film The Blob, a bottle of trichloroacetic acid is tossed at the Blob in a futile attempt to fend it off.
See also
References
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards #0626 National Institute for Occupational Safety and Health (NIOSH)
- ^ ISBN 0911910123
- ^ Databog fysik kemi, F&K Forlaget 11. udgave 2009
- ^ Terchloracetic Acid in Gmelin, L., Hand-book of Chemistry: Organic chemistry
- ^ Jones, Kirtly (June 21, 2012). Marshall, Sarah (ed.). "Trichloroacetic Acid or Bichloroacetic Acid for Genital Warts (Human Papillomavirus)". WebMD. HealthWise. Archived from the original on 16 July 2015.
- PMID 12353208.
- ^ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
- DOI10.2307/4040104.
- OECD SIDS). Accessed June 20, 2014. Archived from the originalon 15 August 2018.
- Cornell PMEP Pesticide Active Ingredient Information database. Archived from the originalon 15 Aug 2020.
- European Chemical Agency. Retrieved 14 March 2022.
- .
- JSTOR 3301070.