Chlornitrofen

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Structural formula
Structural formula of Chlornitrofen
General
Surname Chlornitrofen
other names
  • 1,3,5-trichloro-2- (4-nitrophenoxy) benzene
  • 4-nitrophenyl-2,4,6-trichlorophenyl ether
Molecular formula C 12 H 6 Cl 3 N 1 O 3
Brief description

white solid

External identifiers / databases
CAS number 1836-77-7
EC number 217-407-6
ECHA InfoCard 100.015.825
PubChem 15788
ChemSpider 15011
Wikidata Q11299853
properties
Molar mass 318.54 g mol −1
Physical state

firmly

density

1.53 g cm −3

Melting point

107 ° C

boiling point

210 ° C

solubility
  • practically insoluble in water
  • soluble in xylene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
09 - Dangerous for the environment

Caution

H and P phrases H: 410
P: 273-501
Toxicological data

> 10 g kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlornitrofen is a chemical compound from the group of diphenylether herbicides and nitrophenols .

Extraction and presentation

Chlornitrofen can be obtained by reacting 2,4,6-trichlorophenol with 4-chloronitrobenzene .

properties

Chlornitrofen is a white solid that is practically insoluble in water.

use

Chlornitrofen was used in large quantities as a herbicide on rice fields in Japan between 1965 and 1994 . The compound was then suggested to act as an endocrine disruptor in animals and humans. It acts as a protoporphyrinogen oxidase inhibitor .

Individual evidence

  1. ↑ a b c d e f g h i j data sheet Chlornitrofen, analytical standard at Sigma-Aldrich , accessed on November 2, 2016 ( PDF ).
  2. ↑ a b Entry on Chlornitrofen in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 2, 2016.
  3. ↑ Entry on Chlornitrofen in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 6, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer Science & Business Media, 2012, ISBN 978-3-642-58633-0 , p. 19 ( limited preview in Google Book search).
  5. ↑ Hiroyuki Kojima, Mitsuru Iida, Eiji Katsura, Akio Kanetoshi, Yoshihiro Hori, Kunihiko Kobayashi: Effects of a Diphenyl Ether-type Herbicide, Chlornitrofen, and Its Amino Derivative on Androgen and Estrogen Receptor Activities . In: Environmental Health Perspectives . tape 111 , no. 4 , 2003, p. 497–502 , doi : 10.1289 / ehp.5724 , PMC 1241434 (free full text).
  6. ^ Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Herbicides and plant growth regulators . Royal Society of Chemistry, 1998, ISBN 978-0-85404-494-8 , pp. 317 ( limited preview in Google Book search).