2,4,6-Trichlorophenol Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H351Suspected of causing cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

2,4,6-Trichlorophenol Chemical Properties,Usage,Production

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.]