Chemical Properties
Brown solid; phenol odor. Soluble in sodium hydroxide
solutions and most organic solvents; insoluble
in water.
Uses
Fungicide, wood preservative.
Production Methods
Chlorophenols are generally prepared by the chlorination of
phenol. There are other routes of synthesis as through diazotizing
p-chloroaniline or dechlorinating (by alkaline hydrolysis)
1,2,4,5-tetrachlorobenzene to yield 2,4,5-trichlorophenol
(TCP). Polychlorinated dibenzo-p-dioxins can be
formedduringthemanufacturingprocess of the chlorophenols.
The amount formed depends on temperature and pressure
process variability during production. The more
notable toxic dioxin, 2,3,7,8-tetrachlorodibenzo-p-dioxin
(2,3,7,8-TCDD), is formed during the production of 2,4,5-
TCP. Laboratory reference standards of 2,3,7,8-TCDD are
prepared by heating 2,4,5-TCP under alkaline conditions.
All technical and formulated products containing 2,4,5-TCP
are expected to be contaminated to varying degrees by this
2,3,7,8-TCDD by-product of the manufacturing process.
Definition
ChEBI: The 2,3,5,6-isomer of tetrachlorophenol
General Description
Leaflets (from ligroin) or light beige powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2,3,5,6-TETRACHLOROPHENOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents. .
Hazard
Toxic by ingestion and inhalation, strong
irritant.
Fire Hazard
Flash point data for 2,3,5,6-TETRACHLOROPHENOL are not available. 2,3,5,6-TETRACHLOROPHENOL is probably combustible.
Carcinogenicity
There was no evidence of carcinogenic
activity of 2,4-dichlorophenol in F344/N rats or
B6C3F1 mice from the NTP bioassay program, but
2,4,6-trichlorophenol was reported to be carcinogenic in both
species.
Purification Methods
Crystallise the phenol from pet ethers. The benzoate has m 136o (from EtOH). [Beilstein 6 II 182, 6 III 730, 6 IV 1025.]
