3-chloro-4-methylaniline

Structural formula
General
Surname	3-chloro-4-methylaniline
other names	4-amino-2-chlorotoluene 3-chloro- p -toluidine 1-amino-3-chloro-4-methylbenzene
Molecular formula	C 7 H 8 ClN
Brief description	solid slowly melting at room temperature
External identifiers / databases
CAS number 95-74-9 7745-89-3 (hydrochloride) EC number 202-446-3 ECHA InfoCard 100.002.225 PubChem 7255 ChemSpider 6985 Wikidata Q7602061
properties
Molar mass	141.60 g mol −1
Physical state	liquid or solid
density	1.17 g cm −3
Melting point	24 ° C
boiling point	237-238 ° C
solubility	sparingly soluble in water (2.5 g l −1 at 25 ° C) soluble in ethanol
Refractive index	1.584 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-311-315-317-319-410 P: 273-280-301 + 310-305 + 351 + 338-312-501
Toxicological data	1500 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 . Refractive index: Na-D line , 20 ° C

3-chloro-4-methylaniline is a chemical compound from the group of aminobenzenes and monochloroanilines . The compound's hydrochloride is also known as Starlicid due to its high toxicity to birds.

Extraction and presentation

3-Chloro-4-methylaniline can be obtained by chlorination of p -nitrotoluene and subsequent catalytic reduction on sulfided palladium / activated carbon contacts.

properties

3-chloro-4-methylaniline is a flammable, hardly ignitable solid that melts slowly at room temperature and is sparingly soluble in water. Yellow-brown liquid at temperatures above the melting point. A contaminated product can be liquid even at room temperature. The decomposition temperature of the compound is above 500 ° C, and the decomposition produces hydrogen chloride, among other things. Two stable and one metastable phases of the compound are known.

use

3-chloro-4-methylaniline is used to produce 2-chloro-4-cyanotoluene by the Sandmeyer reaction with copper (I) cyanide . It can also be used as an intermediate in the production of other chemical compounds such as the herbicide chlortoluron . The hydrochloride of 3-chloro-4-methylaniline has been approved for bird control in the USA since 1967.

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on 3-chloro-4-methylaniline in the GESTIS substance database of the IFA , accessed on November 21, 2018(JavaScript required) .
2. ↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 114 ( limited preview in Google Book search).
3. ↑ ^{a b} Data sheet 2-Chloro-4-aminotoluene, 98% from Sigma-Aldrich , accessed on November 21, 2018 ( PDF ).
4. ↑ ^{a b} EPA: Starlicide (3-chloro-p-toluidine hydrochloride)
5. ^ ^{A b} Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry Raw Materials Processes Products . Springer-Verlag, 2013, ISBN 978-3-662-07875-4 , pp. 492 ( limited preview in Google Book search).
6. ↑ SK Roy, B. Amitha, J. Uchil: Study of polymorphism and torsional motions in 3-chloro-4-methylaniline using Cl NQR (nuclear quadrupole resonance). In: Canadian Journal of Physics. 70, 1992, p. 119, doi : 10.1139 / p92-015 .