Dichloroaniline

The dichloroanilines form a group of aromatic compounds that are derived from both aniline and chlorobenzene . The structure consists of a benzene ring with an attached amino group  (–NH ₂ ) and two chlorine  (–Cl) as substituents . Their different arrangement results in six constitutional isomers with the empirical formula C ₆ H ₅ Cl ₂ N. All substances are sparingly soluble in water and are toxic.

Dichloroaniline
Surname	2,3-dichloroaniline	2,4-dichloroaniline	2,5-dichloroaniline	2,6-dichloroaniline	3,4-dichloroaniline	3,5-dichloroaniline
other names	1-amino- 2,3-dichlorobenzene, 2,3-dichlorophenylamine, 2,3-dichlorobenzene amine, 2,3-DCA	1-amino- 2,4-dichlorobenzene, 2,4-dichlorophenylamine, 2,4-dichlorobenzene amine, 2,4-DCA	1-Amino- 2,5-dichlorobenzene, 2,5-dichlorophenylamine, 2,5-dichlorobenzene amine , 2,5-DCA, scarlet GG base	1-amino- 2,6-dichlorobenzene, 2,6-dichlorophenylamine, 2,6-dichlorobenzene amine, 2,6-DCA	1-amino- 3,4-dichlorobenzene, 3,4-dichlorophenylamine, 3,4-dichlorobenzene amine, 3,4-DCA	1-amino- 3,5-dichlorobenzene, 3,5-dichlorophenylamine, 3,5-dichlorobenzene amine, 3,5-DCA
Structural formula
CAS number	608-27-5	554-00-7	95-82-9	608-31-1	95-76-1	626-43-7
PubChem	11844	11123	7262	11846	7257	12281
ECHA InfoCard	100.009.235	100.008.235	100.002.233	100.009.237	100.002.227	100.009.954
Molecular formula	C 6 H 5 Cl 2 N
Molar mass	162.02 g mol −1
Physical state	firmly
Brief description	flammable, crystalline solids
Melting point	23-24 ° C	62 ° C	50 ° C	36-38 ° C	70-72 ° C	51-53 ° C
boiling point	252 ° C	242 ° C	251 ° C	228 ° C	272 ° C	259-260 ° C
density	1.38 g cm −3 (at 20 ° C)	1.56 g cm −3 (at 20 ° C)	1.54 g cm −3 (at 20 ° C)	1.28 g cm −3 (at 20 ° C)	1.57 g cm −3 (at 20 ° C)	1.58 g cm −3 (at 20 ° C)
solubility	0.75–1 g · l −1 (at 20 ° C)	0.45 g l −1 (at 20 ° C)	0.56 g l −1 (at 20 ° C)	1.6 g l −1 (at 20 ° C)	0.58 g l −1 (at 20 ° C)	0.78 g l −1 (at 20 ° C)
Flash point	115 ° C	115 ° C	139 ° C	118 ° C	135 ° C	133 ° C
Ignition temperature		> 600 ° C	> 540 ° C	> 600 ° C	> 600 ° C	620 ° C
GHS labeling	danger				danger	danger
H and P phrases	301-311-331-373-410				301-311-331-317-318-410	301-311-331-373-410
	no EUH phrases
	261-273-280- 301 + 310-501	260-273-280-301 + 310 + 330- 361 + 364-403 + 233	261-273-280- 301 + 310-311-501	261-273-280- 301 + 310-311-501	261-273-280-301 + 310- 305 + 351 + 338-311	261-273-280- 301 + 310-311-501
Tox data		1600 mg kg −1 ( LD 50 ,  rat ,  oral )	1600 mg kg −1 ( LD 50 ,  rat ,  oral )		545 mg kg −1 ( LD 50 ,  rat ,  oral )

presentation

Dichloroanilines may be prepared by hydrogenation of Dichlornitrobenzolen with hydrogen one using noble metal catalyst at temperatures of 80 to 180 ° C and pressures are obtained from 0.3 to 15 MPa.

use

All dichloroanilines are useful as intermediates for the preparation of drugs , dyes , pesticides and plant protection products but also flame retardants and polymers used. So z. B. 3,4-dichloroaniline into Diethofencarb and - processed into diuron via 3,4-dichlorophenyl isocyanate and 3,5-dichloroaniline into vinclozolin . Around 45,000 t of 3,4-dichloroaniline are produced worldwide per year (as of 1997).

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on 2,3-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
2. ↑ ^{a b c d e f g h i j} Entry on 2,4-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
3. ↑ ^{a b c d e f g h i j} Entry on 2,5-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
4. ↑ ^{a b c d e f g h i} Entry on 2,6-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
5. ↑ ^{a b c d e f g h i j} Entry on 3,4-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
6. ↑ ^{a b c d e f g h i} Entry on 3,5-dichloroaniline in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
7. ↑ Toxicological assessment of 3,4-dichloroaniline and 2,5-dichloroaniline (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
8. ↑ Dangers from hormonally active pesticides and biocides. ( Memento from November 9, 2012 in the Internet Archive ) (PDF; 1.1 MB)

Web links

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