Names | |||
---|---|---|---|
Preferred IUPAC name 2,4,6-Trichlorophenol | |||
Identifiers | |||
3D model (JSmol) | |||
776729 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.633 | ||
EC Number |
| ||
3766 | |||
KEGG | |||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
UN number | 2020 | ||
CompTox Dashboard (EPA) | |||
| |||
| |||
Properties | |||
C6H2Cl3OH/C6H3Cl3O | |||
Molar mass | 197.45 g/mol | ||
Appearance | yellow-whitish lumps or powder | ||
Density | 1.4901 g/cm3 at 75 °C [1] | ||
Melting point | 69.5 °C (157.1 °F; 342.6 K) [1] | ||
Boiling point | 249 °C (480 °F; 522 K) [1] | ||
0.069 g/100 g H2O [2] | |||
Hazards | |||
GHS labelling: | |||
Warning | |||
H302, H315, H319, H351, H410 | |||
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P391, P405, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, [3] defoliant, and glue preservative. [4] It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.
2,4,6-Trichlorophenol is produced industrially by the electrophilic chlorination of phenol: [5]
In animal models, consumption of 2,4,6-trichlorophenol leads to an increased incidence of lymphomas, leukemia, and liver cancer. [6] [7] It is classified as Group B2 (probable human carcinogen) by the United States Environmental Protection Agency. [7] The technical grade of this substance may contain polychlorinated dibenzodioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and other contaminants. [8]
2,4,6-Trichlorophenol is an environmental pollutant that has been found in fresh water lakes such as the Great Lakes. [9]
The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.
Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in contrast to molecular hydrides such as borane, silane, germane, ammonia, and methane. It is an ionic material that is insoluble in all solvents (other than molten sodium metal), consistent with the fact that H− ions do not exist in solution.
Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.
2,4,6-Trichloroanisole (TCA) is a chemical compound that represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products. As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines, and it has an unpleasant earthy, musty and moldy smell.
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.
A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. There are five basic types of chlorophenols and 19 different chlorophenols in total when positional isomerism is taken into account. Chlorophenols are produced by electrophilic halogenation of phenol with chlorine.
4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.
Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, synthetic perfumes and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.
Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.
1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C3H4Cl2. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is banned in 34 countries.
Hexachlorocyclohexa-2,5-dien-1-one, sometimes informally called hexachlorophenol (HCP) is an organochlorine compound. It can be prepared from phenol. Despite the informal name, the compound is not a phenol but is a ketone. The informal name is derived from its method of preparation which includes phenol as a reagent.
2-Aminophenol is an organic compound with the formula C6H7NO. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallized from hot water.
Hexachlorobutadiene, (often abbreviated as "HCBD") Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds. Structurally, it has a 1,3-butadiene core, but fully substituted with chlorine atoms.
2,4-Dichlorophenol (2,4-DCP) is a chlorinated derivative of phenol with the molecular formula Cl2C6H3OH. It is a white solid that is mildly acidic (pKa = 7.9). It is produced on a large scale as a precursor to the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D).
Dichlorophenols (DCPs) are any of several chemical compounds which are derivatives of phenol containing two chlorine atoms. There are six isomers:
2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).
3-Chlorophenol is an organic compound with the molecular formula C6H4ClOH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene.
4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.
Dichloroacetaldehyde is a chlorinated aldehyde with the chemical formula HCCl2CHO. Along with monochloroacetaldehyde and trichloroacetaldehyde, it is one of the three possible chlorinated acetaldehydes.