2,3,5,6-TETRACHLOROPHENOL

Chemical properties

Brown solid; phenol odor. Soluble in sodium hydroxide solutions and most organic solvents; insoluble in water.

The Uses of 2,3,5,6-TETRACHLOROPHENOL

Fungicide, wood preservative.

Definition

ChEBI: The 2,3,5,6-isomer of tetrachlorophenol

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.

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.]