Tetrachlorophenols

Tetrachlorophenols
Surname	2,3,4,5-tetrachlorophenol	2,3,4,6-tetrachlorophenol	2,3,5,6-tetrachlorophenol
other names	2,3,4,5-TeCP	2,3,4,6-TeCP Dowicide 6	2,3,5,6-TeCP
Structural formula
CAS number	4901-51-3	58-90-2	935-95-5
	25167-83-3 (mixture of isomers)
PubChem	21013	6028	13636
Molecular formula	C 6 H 2 Cl 4 O
Molar mass	231.89 g mol −1
Physical state	firmly
Brief description	colorless to gray crystal needles with a phenol-like odor
Melting point	69-70 ° C	68 ° C	113-114 ° C
boiling point	164 ° C (31 mbar)	150 ° C (21 mbar)	288 ° C (decomposition)
density	1.6 g cm −3 (80 ° C)	1.6 g cm −3 (60 ° C)
solubility		<1 g l −1 (20 ° C)
	poorly soluble in water
GHS labeling	danger	danger	danger
H and P phrases	301-315-318-335-400	301-319-315-410	301-315-318-335
	no EUH phrases	no EUH phrases	no EUH phrases
	261-273-280-301 + 310 305 + 351 + 338	273-301 + 310 305 + 351 + 338-501	261-280-301 + 310 305 + 351 + 338

The tetrachlorophenols form a group of organochlorine compounds, consisting of a benzene ring with four chlorine atoms  (–Cl) and a hydroxyl group  (–OH) as substituents . Their different arrangement results in three constitutional isomers with the empirical formula C ₆ H ₂ Cl ₄ O.

Extraction and presentation

2,3,4,6-Tetrachlorophenol is considered an impurity in technical pentachlorophenol and is a by-product of its manufacture.

properties

The boiling points of the three isomers are relatively close to one another, while their melting points differ more clearly. The 2,3,5,6-tetrachlorophenol, which has the highest symmetry, has the highest melting point. The tetrachlorophenols are sparingly soluble in water and react slightly acidic in solution.

use

2,3,4,6-Tetrachlorophenol is used in the manufacture of pharmaceuticals, fertilizers and pesticides and is used as a wood preservative. Sodium 2,3,5,6-tetrachlorophenolate (the sodium salt of 2,3,5,6-tetrachlorophenol, CAS number: 85712-07-8) is used as a fungicide .

safety instructions

The decomposition of tetrachlorophenols produces hydrogen chloride and other highly toxic chlorine products such as PCDD / PCDF. The compounds are very toxic to aquatic organisms.

literature

• Jennifer M. Gee, JL Peel: Metabolism of 2,3,4,6-Tetrachlorophenol by Micro-organisms from Broiler House Litter . In: Microbiology . tape 85 , no. 2 , 1974, p. 237–243 , doi : 10.1099 / 00221287-85-2-237 (free full text).

Individual evidence

1. ↑ ^{a b c d e f} Entry on 2,3,4,5-tetrachlorophenol in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
2. ↑ ^{a b c d e} Entry on 2,3,4,6-tetrachlorophenol in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
3. ↑ ^{a b c d} Entry on 2,3,5,6-tetrachlorophenol in the GESTIS substance database of the IFA , accessed on October 14, 2012(JavaScript required) .
4. ↑ Data sheet 2,3,4,6-tetrachlorophenol from Sigma-Aldrich , accessed on July 1, 2011 ( PDF ).
5. ↑ 2,3,4,6-tetrachlorophenol (Enius)
6. ↑ 2,3,4,6-tetrachlorophenol (SpecLab)