2,4,6-Trichlorophenol
2,4,6-Trichlorophenol Basic information
- Product Name:
- 2,4,6-Trichlorophenol
- Synonyms:
-
- 2,4,6-trichloro-pheno
- ai3-00142
- caswellno.880c
- Dowcide 2S
- dowcide2s
- epapesticidechemicalcode064212
- NCI-C02904
- phenaclor
- CAS:
- 88-06-2
- MF:
- C6H3Cl3O
- MW:
- 197.45
- EINECS:
- 201-795-9
- Product Categories:
-
- Agro-Products
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- TP - TZ
- Organic Building Blocks
- Oxygen Compounds
- Phenols
- Alpha Sort
- Analytical Standards
- Pesticides&Metabolites
- Q-ZAlphabetic
- Method 552Analytical Standards
- 500 Series Drinking Water Methods
- ChloroEPA
- TP - TZMore...Close...
- Phenoles and thiophenoles
- AromaticsChemical Class
- Chemical Class
- ChloroAnalytical Standards
- Halogenated
- PhenolsVolatiles/ Semivolatiles
- T-ZAlphabetic
- Mol File:
- 88-06-2.mol
2,4,6-Trichlorophenol Chemical Properties
- Melting point:
- 64-66 °C(lit.)
- Boiling point:
- 246 °C(lit.)
- Density
- 1.49
- vapor pressure
- 1 mm Hg ( 76.5 °C)
- refractive index
- 1.5300 (estimate)
- Flash point:
- 99 °C
- storage temp.
- Store below +30°C.
- solubility
- 0.8g/l
- form
- Crystalline Mass or Crystalline Powder and Chunks
- pka
- 6.15 (Leuenberger et al., 1985)
6.10 (Blackman et al., 1955)
6.0 (Eder and Weber, 1980) - color
- white to slightly brown
- Water Solubility
- 0.8 g/L
- Merck
- 14,9644
- BRN
- 776729
- Henry's Law Constant
- 9.07 at 25 °C (estimated, Leuenberger et al., 1985a)
- CAS DataBase Reference
- 88-06-2(CAS DataBase Reference)
- IARC
- 2B (Vol. 117) 2019
- NIST Chemistry Reference
- Phenol, 2,4,6-trichloro-(88-06-2)
- EPA Substance Registry System
- 2,4,6-Trichlorophenol (88-06-2)
Safety Information
- Hazard Codes
- Xn,N,T,F
- Risk Statements
- 22-36/38-50/53-40-52/53-39/23/24/25-23/24/25-11-51/53
- Safety Statements
- 36/37-60-61-45-16
- RIDADR
- UN 3077 9/PG 3
- WGK Germany
- 3
- RTECS
- SN1575000
- TSCA
- Yes
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 29081000
- Hazardous Substances Data
- 88-06-2(Hazardous Substances Data)
- Toxicity
- LD50 orally in Rabbit: 887 mg/kg
MSDS
- Language:English Provider:2,4,6-TCP
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
2,4,6-Trichlorophenol Usage And Synthesis
Description
2,4,6-Trichlorophenol is a colorless to yellow solid that has a strong phenol-like smell. It decomposes at elevated temperatures when heated to produce corrosive and toxic fumes including chlorine and hydrogen chloride. It is soluble in organic solvents and partially soluble in water.
Previously, it was used in the manufacture of other chemicals. Moreover, it was also used as an antiseptic, a pesticide for leather, wood, and preservation of glue as well as an anti-mildew treatment. Nevertheless, the production of 2,4,6-Trichlorophenol was discontinued in America in the 1980s.
Health Effects
Human beings may be exposed to 2,4,6-Trichlorophenol via inhalation and can cause altered pulmonary functions, respiratory effects, and pulmonary lesions. Moreover, 2,4,6-trichlorophenol can irritate the lungs and throat causing coughing and wheezing. In animal models, ingestion of 2,4,6-trichlorophenol caused an increase in occurrences of leukemia, lymphoma, and liver cancer. As such, 2,4,6-Trichlorophenol might be a carcinogenic in humans.
Contact can severely burn and irritate the eyes and skin with possible eye damage. Elevated exposures may cause weakness, restlessness, rapid breathing, shaking, tremors, coma, seizures, or even death.
Extreme exposure to 2,4,6-trichlorophenol can have devastating effect on a developing fetus. Other long-term effect to repeated exposure may cause bronchitis with shortness of breath.
Chemical Properties
Yellow flakes; strong phenolic odor. Soluble in acetone, alcohol, and ether; insoluble in water. Nonflammable.
Physical properties
Colorless needles or yellow solid with a strong, phenolic, musty or rotten vegetable-type odor. At 40 °C, the lowest concentration at which an odor was detected was 380 μg/L. At 25 °C, the lowest concentration at which a taste was detected was >12 μg/L (Young et al., 1996).
Uses
Wood preservative; disinfectant; fungicide, herbicide, defoliant.
Uses
2,4,6-Trichlorophenol is used as a broad range pesticide against insects, fungi, vegetation and bacteria. It has become a common environmental contaminant and probable human carcinogen.
Uses
Fungicide, herbicide, defoliant.
Definition
ChEBI: A trichlorophenol with phenolic substituents on positions 2, 4 and 6.
Synthesis Reference(s)
The Journal of Organic Chemistry, 24, p. 1523, 1959 DOI: 10.1021/jo01092a034
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2,4,6-Trichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents. 2,4,6-Trichlorophenol can be converted to the sodium salt by reaction with sodium carbonate. Forms ethers, esters and salts by reaction with metals and amines. Undergoes substitution reactions such as nitration, alkylation, acetylation and halogenation. Can be hydrolyzed by reaction with bases at elevated temperatures and pressures. Reacts with alkalis at high temperatures .
Health Hazard
In experimental animals, 2,4,6- trichlorophenol causes toxic effects to the liver and hematologic system and cancer. There is no reliable information regarding exposure and toxic effects in humans.
Fire Hazard
Literature sources indicate that 2,4,6-Trichlorophenol is nonflammable.
Safety Profile
Confirmed carcinogen with experimental carcinogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and skin contact. A skin and severe eye irritant. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-. Used as a germicide and preservative. See also CHLOROPHENOLS.
Carcinogenicity
2,4,6-Trichlorophenol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Biological. In activated sludge, only 0.3% mineralized to carbon dioxide after 5 d (Freitag et al.,
1985). In anaerobic sludge, 2,4,6-trichlorophenol degraded to 4-chlorophenol (Mikesell and Boyd,
1985). When 2,4,6-trichlorophenol was statically incubated in the dark at 25 °C with yeast extract
and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was
observed. At concentrations of 5 and 10 mg/L, 96 and 97% biodegradation, respectively, were
observed after 7 d (Tabak et al., 1981).
Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ
= 365 nm) converted 2,4,6-trinitrophenol to carbon dioxide at a significant rate (Matthews, 1986).
A carbon dioxide yield of 65.8% was achieved when 2,4,6-trichlorophenol adsorbed on silica gel
was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. An aqueous solution containing chloramine reacted with 2,4,6-trichlorophenol
to yield the following intermediate products after 2 h at 25 °C: 2,6-dichloro-1,4-
benzoquinone-4-(N-chloro)imine and 4,6-dichloro-1,2-benzoquinone-2-(N-chloro)imine (Maeda et
al., 1987).
Purification Methods
Crystallise the phenol from *benzene, EtOH or EtOH/water. [Beilstein 6 IV 1005.]
2,4,6-Trichlorophenol Preparation Products And Raw materials
Preparation Products
Raw materials
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2,4,6-Trichlorophenol(88-06-2)Related Product Information
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- 2,4,6-TRICHLOROANISOLE
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