4-chloro- o -toluidine

Structural formula
General
Surname	4-chloro- o -toluidine
other names	1-amino-4-chloro-2-methylbenzene 4-chloro-2-methylaniline 2-amino-5-chlorotoluene 5-chloro-2-aminotoluene Real red TR base Fast Red TR Base
Molecular formula	C 7 H 8 ClN
Brief description	colorless to brown crystal mass with an aniline- like odor
External identifiers / databases
CAS number 95-69-2 EC number 202-441-6 ECHA InfoCard 100.002.220 PubChem 7251 ChemSpider 6981 Wikidata Q10859489
properties
Molar mass	141.60 g mol −1
Physical state	firmly
density	1.14 g cm −3
Melting point	30 ° C
boiling point	241 ° C
solubility	practically insoluble in water
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301-311-331-341-350-410 P: 201-261-273-280-301 + 310-311
MAK	Switzerland: 2 ml m −3 or 12 mg m −3
Toxicological data	1060 mg 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 .

4-chloro- o -toluidine ( p -chloro- o -toluidine) is a chemical compound from the group of toluidines . The aromatic amino compound is a carcinogen that leads to bladder cancer .

4-chloro- o -toluidine was produced industrially in Germany from 1924.

use

• 4-chloro- o -toluidine can be used as a diazo component for the synthesis of azo dyes .
• The compound is the starting material for the insecticide chlordimeform .
• Fast Red Salt TR:
  4-chloro- o -toluidine is the starting material for Fast Red Salt TR ( CI Azoic Diazo Component 11), a stabilized diazonium salt for the production of developing dyes . It is used in biochemistry for immunostaining with an alkaline phosphatase and reacts with naphtol AS-MX-phosphate after its enzymatic hydrolysis to form a red azo dye that is insoluble in aqueous solutions , e.g. B. Western blotting and immunohistochemistry .
• Naphtol AS-TR phosphate:
  By reacting 4-chloro- o -toluidine with the acid chloride of 2-hydroxynaphthalene-3-carboxylic acid, naphthol AS-TR is accessible, which can be converted to the phosphoric ester naphtol AS-TR phosphate. Analogous to Naphtol AS-MX-Phosphat , this compound can be used as a substrate for the determination of alkaline phosphatase in cells .

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on 4-chloro-o-toluidine in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
2. ↑ Entry on 4-chloro-o-toluidine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
3. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 95-69-2 or 4-chloro-o-toluidine ), accessed on November 2, 2015.
4. ^ W. Popp, W. Schmieding, M. Speck, C. Vahrenholz, K. Norpoth: Incidence of bladder cancer in a cohort of workers exposed to 4-chloro-o-toluidine while synthesizing chlordimeform. In: British Journal of Industrial Medicine . Volume 49, Number 8, August 1992, pp. 529-531, ISSN  0007-1072 . PMID 1515344 . PMC 1039284 (free full text).
5. ↑ Urinary bladder cancer and its trade association aspects
6. ^ IARC monograph on 4-CHLORO- ortho -TOLUIDINE
7. ↑ Data sheet 4-Chloro-2-methylbenzenediazonium salt, Azoic Diazo No. 11 at Sigma-Aldrich , accessed on September 12, 2016 ( PDF ).
8. ↑ Kim S Suvarna: Bancroft's Theory and Practice of Histological Techniques. Elsevier Health Sciences, 2012, ISBN 978-0-702-05032-9 , p. 421. - Practical blood cell diagnostics .
9. ↑ James W. Goding: Monoclonal Antibodies. Academic Press, 1996, ISBN 978-0-080-53695-8 , p. 418.