Chrysoidine

Structural formula
General
Surname	Chrysoidine
other names	4 - [( E ) -phenyldiazenyl] -1,3-benzenediamine ( IUPAC ); CI Solvent Orange 3; CI 11270; 4- (phenylazo) benzene-1,3-diamine; 2,4-diaminoazobenzene; Chrysoidin Y / G;
Molecular formula	C 12 H 12 N 4
Brief description	yellow needles
External identifiers / databases
EC number	207-803-7
ECHA InfoCard	100.007.095
PubChem	10317
ChemSpider	9895
Wikidata	Q26840899
properties
Molar mass	212.25 g mol −1
Physical state	firmly
Melting point	117.5 ° C
solubility	poorly soluble in water; soluble in alcohol and ether;
safety instructions
H and P phrases	H: 302-315-341-410
	P: 273-281-501
Toxicological data	1650 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 .

Chrysoidin or 2,4-diaminoazobenzene is an azo dye that was discovered by Heinrich Caro in 1875 and specifically synthesized by Otto Nikolaus Witt in 1876 . The dye with the color index name Solvent Orange 3 belongs to the application group of solvent dyes . The hydrochloride of chrysoidin, on the other hand, is the cationic dye CI Basic Orange 2.

synthesis

Chrysoidin can be prepared by an azo coupling of diazotized aniline with 1,3-diaminobenzene .

use

Chrysoidin is approved for coloring tannin-stained cotton, leather and paper as well as in histology for coloring Corynebacterium diphtheriae . On the other hand, use in cosmetic products is prohibited. The dye is used in FCA staining in botany.

Chrysoidin dyes wool, silk and stained cotton golden yellow, pulling a little orange.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2,4-diaminoazobenzene. In: Römpp Online . Georg Thieme Verlag, accessed on July 6, 2014.
↑ ^a ^b ^c ^d Entry on chrysoidin in the GESTIS substance database of the IFA , accessed on February 8, 2018(JavaScript required) .
↑ External identifiers or database links for chrysoidin hydrochloride (CI Basic Orange 2) : CAS number: 532-82-1, EC number: 208-545-8, ECHA -InfoCard: 100.007.770 , GESTIS- Substance database : 104818 , PubChem : 10771 , ChemSpider : 10468547 , Wikidata : Q17522036 .

↑ Entry on 4- (phenylazo) benzene-1,3-diamine 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 .

↑ Otto Nikolaus Witt: The Chrysoïdin and its implementations . In: Reports of the German Chemical Society . tape 10 , no. 1 , January 1877, p. 654–662 , doi : 10.1002 / cber.187701001183 ( PDF ).

↑ Fuchsin-Chrysoidin-Astrablau according to Etzold (FCA staining)

↑ Adolf Beythien, Ernst Dressler (Ed.): Merck's Lexicon of Goods for Trade, Industry and Commerce . 7th edition. Leipzig 1920, ISBN 3-933497-13-2 , entry on chrysoidin (reprint: Manuscriptum, Recklinghausen 1996): “(Diamidoazobenzene hydrochloride, diamidoazobenzene hydrochloric acid), a yellow tar dye belonging to the group of azo dyes, is produced by the action of metaphenylenediamine on hydrochloric acid diazobenzene . It dissolves in water and dyes wool and silk, as well as cotton stained with tannin, golden yellow, turning a little orange. The hot, concentrated, aqueous solution turns into a blood-red gel when it cools. "

[roempp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2,4-diaminoazobenzene. In: Römpp Online . Georg Thieme Verlag, accessed on July 6, 2014.

[GESTIS-2] Entry on chrysoidin in the GESTIS substance database of the IFA , accessed on February 8, 2018(JavaScript required) .

[3] External identifiers or database links for chrysoidin hydrochloride (CI Basic Orange 2) : CAS number: 532-82-1, EC number: 208-545-8, ECHA -InfoCard: 100.007.770 , GESTIS- Substance database : 104818 , PubChem : 10771 , ChemSpider : 10468547 , Wikidata : Q17522036 .

[CLP_100.007.095-4] Entry on 4- (phenylazo) benzene-1,3-diamine 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 .

[5] Otto Nikolaus Witt: The Chrysoïdin and its implementations . In: Reports of the German Chemical Society . tape 10 , no. 1 , January 1877, p. 654–662 , doi : 10.1002 / cber.187701001183 ( PDF ).

[6] Fuchsin-Chrysoidin-Astrablau according to Etzold (FCA staining)

[7] Adolf Beythien, Ernst Dressler (Ed.): Merck's Lexicon of Goods for Trade, Industry and Commerce . 7th edition. Leipzig 1920, ISBN 3-933497-13-2 , entry on chrysoidin (reprint: Manuscriptum, Recklinghausen 1996): “(Diamidoazobenzene hydrochloride, diamidoazobenzene hydrochloric acid), a yellow tar dye belonging to the group of azo dyes, is produced by the action of metaphenylenediamine on hydrochloric acid diazobenzene . It dissolves in water and dyes wool and silk, as well as cotton stained with tannin, golden yellow, turning a little orange. The hot, concentrated, aqueous solution turns into a blood-red gel when it cools. "