1-aminoanthraquinone

Structural formula
General
Surname	1-aminoanthraquinone
other names	1-amino-9,10-anthracenedione; CI 37275;
Molecular formula	C 14 H 9 NO 2
Brief description	dark brown solid
External identifiers / databases
EC number	201-423-5
ECHA InfoCard	100.001.294
PubChem	6710
Wikidata	Q27284591
properties
Molar mass	223.23 g mol −1
Physical state	firmly
Melting point	253-255 ° C
boiling point	> 300 ° C
Vapor pressure	1.2 · 10 −4 Pa (100 ° C)
solubility	practically insoluble in water (20 mg l −1 at 20 ° C); soluble in ethanol , benzene , chloroform , ether , glacial acetic acid , hydrogen chloride (20 mg l −1 at 20 ° C);
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , mouse , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-Aminoanthraquinone is a chemical compound from the group of anthraquinone derivatives .

Extraction and presentation

The most important production methods for 1-aminoanthraquinone are the reaction of anthraquinone sulfonic acid ( 2 ) with ammonia, or the reduction of 1-nitroanthraquinone ( 3 ), which is accessible by nitration of anthraquinone ( 1 ).

Synthesis of 1-aminoanthraquinone from anthraquinone

The reduction of nitroanthraquinone is carried out , for example, with sodium sulfide or sodium hydrogen sulfide . As an alternative to reduction, it is also possible to replace the nitro group with the amino group , this reaction being mainly used in the preparation of secondary amines.

An alternative method for the preparation of 1-aminoanthraquinone by building up the anthraquinone skeleton starts from 5-nitronaphthoquinone .

Synthesis of 1-aminoanthraquinone from 5-nitronaphthoquinone

By reacting 1,3-butadiene ( 1 ) with 5-nitronaphthoquinone ( 2 ) in the sense of a Diels-Alder reaction , 5-nitro-1,4,4a, 9a-tetrahydroanthraquinone ( 3 ) is obtained. Oxidation converts 3 into 1-nitroanthraquinone ( 4 ), which is then reduced to 1-aminoanthraquinone ( 5 ).

properties

1-Aminoanthraquinone is a flammable, difficult to ignite, crystalline, dark brown solid that is practically insoluble in water.

use

1-Aminoanthraquinone is used as an intermediate in the manufacture of anthraquinone dyes and drugs.

An important intermediate dye product is bromamic acid ( 1-amino-4-bromoanthraquinone-2-sulfonic acid ) ( 6 ), which can be obtained from 1-aminoanthraquinone ( 4 ) via sulfonation with chlorosulfonic acid or oleum and subsequent bromination .

Synthesis of bromamic acid

Web links

Professional association raw materials and chemical industry: TOXICOLOGICAL REVIEWS in long version (05/2002) 1-Aminoanthraquinone , accessed on May 16, 2019

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-aminoanthraquinone in the GESTIS substance database of the IFA , accessed on May 16, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Anthraquinone, 1-amino- , accessed on May 16, 2019.
↑ Data sheet 1-Aminoanthraquinone, 97% from AlfaAesar, accessed on May 16, 2019 ( PDF )(JavaScript required) .
↑ Entry on Aminoanthraquinones. In: Römpp Online . Georg Thieme Verlag, accessed on May 21, 2019.
↑ Willy Herbst, Klaus Hunger: Industrial Organic Pigments Production, Properties, Applications . John Wiley & Sons, 2006, ISBN 978-3-527-60406-7 , pp. 501 ( limited preview in Google Book search).
↑ Hans-Samuel Bien, Klaus Wunderlich: Anthraquinone dyes and intermediates . In: Ullmann's Encyclopedia of Technical Chemistry . 4th edition. tape 7 . Verlag Chemie, Weinheim 1974, ISBN 3-527-20000-2 , pp. 585 ff .
↑ Patent application DE2539631 : Process for the production of high-purity 5-nitro-1,4,4A, 9A-tetrahydroanthraquinone. Applied September 5, 1975 , published March 18, 1976 , Applicant: Mitsui Toatsu Chemicals, Inventor: Torisu Yasuyoshi, Kaba Seishichiro, Mukai Ken. ‌
↑ EN Abrahart: Dyes and Their Intermediates . 2nd Edition. Edward Arnold (Publishers) Ltd., London 1977, ISBN 0-7131-2580-2 , pp. 41-42 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-aminoanthraquinone in the GESTIS substance database of the IFA , accessed on May 16, 2019(JavaScript required) .

[INCHEM-2] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Anthraquinone, 1-amino- , accessed on May 16, 2019.

[Alfa-3] Data sheet 1-Aminoanthraquinone, 97% from AlfaAesar, accessed on May 16, 2019 ( PDF )(JavaScript required) .

[4] Entry on Aminoanthraquinones. In: Römpp Online . Georg Thieme Verlag, accessed on May 21, 2019.

[Willy_Herbst,_Klaus_Hunger-5] Willy Herbst, Klaus Hunger: Industrial Organic Pigments Production, Properties, Applications . John Wiley & Sons, 2006, ISBN 978-3-527-60406-7 , pp. 501 ( limited preview in Google Book search).

[6] Hans-Samuel Bien, Klaus Wunderlich: Anthraquinone dyes and intermediates . In: Ullmann's Encyclopedia of Technical Chemistry . 4th edition. tape 7 . Verlag Chemie, Weinheim 1974, ISBN 3-527-20000-2 , pp. 585 ff .

[7] Patent application DE2539631 : Process for the production of high-purity 5-nitro-1,4,4A, 9A-tetrahydroanthraquinone. Applied September 5, 1975 , published March 18, 1976 , Applicant: Mitsui Toatsu Chemicals, Inventor: Torisu Yasuyoshi, Kaba Seishichiro, Mukai Ken. ‌

[8] EN Abrahart: Dyes and Their Intermediates . 2nd Edition. Edward Arnold (Publishers) Ltd., London 1977, ISBN 0-7131-2580-2 , pp. 41-42 .