Dichlorophenols

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The dichlorophenols ( DCP ) form a group of aromatic compounds from the group of chlorophenols , which are derived from phenol as well as from chlorobenzene or dichlorobenzenes . The structure consists of a benzene ring with an attached hydroxyl group  (-OH) and two chlorine atoms  (-Cl) as substituents . Their different arrangement results in six constitutional isomers . They have the empirical formula C 6 H 4 Cl 2 O, a molar mass of 163.00 g / mol and are in the form of colorless crystal needles. During their production, polychlorinated dibenzodioxins and dibenzofurans are produced as by-products under unfavorable conditions . In particular, 2,4-dichlorophenol is used in the manufacture of herbicides .

properties

Dichlorophenols
Surname 2,3-dichlorophenol,
1,2-dichloro-
3-hydroxybenzene 		2,4-dichlorophenol ,
1-hydroxy-
2,4-dichlorobenzene 		2,5-dichlorophenol,
1,4-dichloro-
2-hydroxybenzene 		2,6-dichlorophenol,
1,3-dichloro-
2-hydroxybenzene 		3,4-dichlorophenol,
1,2-dichloro-
4-hydroxybenzene 		3,5-dichlorophenol,
1,3-dichloro-
5-hydroxybenzene
Structural formula 2,3-dichlorophenol.svg 2,4-dichlorophenol.svg 2,5-dichlorophenol.svg 2,6-dichlorophenol.svg 3,4-dichlorophenol.svg 3,5-dichlorophenol.svg
CAS number 576-24-9 120-83-2 583-78-8 87-65-0 95-77-2 591-35-5
25167-81-1 (mixture of isomers)
PubChem 11334 8449 66 6899 7258 11571
ECHA InfoCard 100.008.546 100.004.027 100.008.657 100.001.602 100.002.228 100.008.833
100.042.433 (mixture of isomers)
Molecular formula C 6 H 4 Cl 2 O
Molar mass 163.00 g mol −1
Physical state firmly
Brief description flammable, colorless to yellowish crystal needles with a phenol-like odor
Melting point 56-57 ° C 40-43 ° C 56-58 ° C 64-66 ° C 68 ° C 65-67 ° C
boiling point 206 ° C 209-211 ° C 211 ° C 218-220 ° C 253 ° C 233 ° C
solubility poorly soluble in water
GHS
labeling
07 - Warning 09 - Dangerous for the environment
Caution
05 - Corrosive 06 - Toxic or very toxic

09 - Dangerous for the environment
danger
07 - Warning 09 - Dangerous for the environment
danger
05 - Corrosive
Caution
05 - Corrosive 07 - Warning
danger
06 - Toxic or very toxic 07 - Warning

09 - Dangerous for the environment
danger
H and P phrases 319-302 + 312-315-411 302-311-314-411 302-315-319-335-411 314 302-315-318 302-311-314-411
no EUH phrases no EUH phrases no EUH phrases no EUH phrases no EUH phrases no EUH phrases
280-302 + 352
305 + 351 + 338-273-501 		273-280-301 + 330 + 331
302 + 350-305 + 351 + 338-310 		273-280-301 + 312
302 + 352-305 + 351 + 338 		280-302 + 352-305 + 351 + 338 280-305 + 351 + 338 273-280-305 + 351 + 338-310
LD 50 2376 mg kg −1
oral, mouse 		47 mg kg −1
oral, rat 		580 mg kg −1
oral, rat 		- 1685 mg kg −1
oral, mouse 		2389 mg kg −1
oral, mouse

use

2,4-dichlorophenol is used in moth repellants and as an antifungal agent in stockings, shoe insoles, etc. as well as in the manufacture of herbicides such as 2,4-dichlorophenoxyacetic acid , which made up half of the defoliant Agent Orange used in the Vietnam War . 3,5-dichlorophenol is used as a reference substance in some standardized bio-test procedures for water, such as the luminescent bacteria test.

Biological importance

2,6-dichlorophenol is used as a pheromone by the females of 14 tick species and 2,4-dichlorophenol is produced as a growth hormone by penicillin molds .

Individual evidence

  1. ↑ a b Entry on dichlorophenol, isomers in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  2. ↑ a b c d Entry on 2,3-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  3. ↑ a b c d Entry on 2,4-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  4. ↑ a b c d Entry on 2,5-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  5. ↑ a b c d Entry on 2,6-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  6. ↑ a b c Entry on 3,4-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  7. ↑ a b c d Entry on 3,5-dichlorophenol in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
  8. ↑ Data sheet 3,4-dichlorophenol from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
  9. ↑ a b c d e f data sheet at chemicalland21.com
  10. ↑ Gordon W. Gribble: Environmental poisons from the gift table of nature . In: Spectrum of Science 06/2005.

Web links

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