2-aminonaphthalene-1-sulfonic acid

Structural formula
General
Surname	2-aminonaphthalene-1-sulfonic acid
other names	2-amino-1-naphthalenesulfonic acid; 2-naphthylamine-1-sulfonic acid; Tobias acid;
Molecular formula	C 10 H 9 NO 3 S
Brief description	light brown solid
External identifiers / databases
EC number	201-331-5
ECHA InfoCard	100.001.211
PubChem	6670
Wikidata	Q11751621
properties
Molar mass	223.25 g mol −1
Physical state	firmly
solubility	sparingly soluble in water (4.1 g l −1 at 20 ° C); very slightly soluble in ethanol and diethyl ether ;
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	19400 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 .

2-aminonaphthalene-1-sulfonic acid is a chemical compound from the group of aminobenzenes and letter acids . It is also called Tobias acid , after the German chemist Georg Tobias . It belongs to the polycyclic aromatic hydrocarbons (PAH) class of substances .

Extraction and presentation

2-aminonaphthalene-1-sulfonic acid can be obtained by sulfonation of beta-naphthol with chlorosulfonic acid in nitrobenzene at 0 ° C, followed by heating the resultant 1-sulfonic acid with ammonium hydrogen and ammonia at 145-150 ° C ( Bucherer reaction ) are obtained. It is also possible to prepare by sulfonation of 2-naphthylamine or by amination of the corresponding hydroxynaphthalenesulfonic acid .

properties

2-aminonaphthalene-1-sulfonic acid is a flammable, difficult to ignite, crystalline, light brown solid that is sparingly soluble in water.

use

2-Aminonaphthalene-1-sulfonic acid is used as an intermediate in the production of other chemical compounds [such as 2- (2-naphthylamino) benzoxazole or dyes].

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-aminonaphthalene-1-sulfonic acid in the GESTIS substance database of the IFA , accessed on November 6, 2018(JavaScript required) .
↑ BAuA: Rationale on 2-aminonaphthalene-1-sulfonic acid in TRGS 900 , accessed on November 6, 2018.
↑ Alexander Senning: Elsevier's Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology . Elsevier, 2006, ISBN 978-0-08-048881-3 , pp. 394 ( limited preview in Google Book search).
↑ Entry on 2-amino-1-naphthalenesulfonic acid in the Hazardous Substances Data Bank , accessed on November 6, 2018.
↑ Beth-Hübner, M., Brandt, B., Rupp, R., Neumann, V., Eickmann, U., Lindner, G., Auras, S., Fröhlich, H.-P., Isringhausen, A. , Kraus, W., Pucknat, D., Pucknat, U., Neumeister, L., Seibel, J., Fauss, J., Brüning, T., Käfferlein, HU, Taeger, D., Weiß, T., Fritz, C., Breuer, D., Giesen, Y., Pflaumbaum, W .: Aromatic Amines A working aid in the determination of occupational diseases . DGUV / IFA, 2018, ISBN 3-86423-225-2 , p. 75 ( limited preview in Google Book search).
↑ Data sheet 2-Amino-1-naphthalenesulfonic acid, 98% from Sigma-Aldrich , accessed on November 6, 2018 ( PDF ).
↑ Maximilian Zander: Polycyclic aromatic hydrocarbons and fullerenes . Springer-Verlag, 2013, ISBN 978-3-322-96707-7 , p. 195 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-aminonaphthalene-1-sulfonic acid in the GESTIS substance database of the IFA , accessed on November 6, 2018(JavaScript required) .

[2] BAuA: Rationale on 2-aminonaphthalene-1-sulfonic acid in TRGS 900 , accessed on November 6, 2018.

[Alexander_Senning-3] Alexander Senning: Elsevier's Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology . Elsevier, 2006, ISBN 978-0-08-048881-3 , pp. 394 ( limited preview in Google Book search).

[HSDB-4] Entry on 2-amino-1-naphthalenesulfonic acid in the Hazardous Substances Data Bank , accessed on November 6, 2018.

[Beth-Hübner,_M.,_Brandt,_B.,_Rupp,_R.,_Neumann,_V.,_Eickmann,_U.,_Lindner,_G.,_Auras,_S.,_Fröhlich,_H.-P.,_Isringhausen,_A.,_Kraus,_W.,_Pucknat,_D.,_Pucknat,_U.,_Neumeister,_L.,_Seibel,_J.,_Fauss,_J.,_Brüning,_T.,_Käfferlein,_H._U.,_Taeger,_D.,_Weiß,_T.,_Fritz,_C.,_Breuer,_D.,_Giesen,_Y.,_Pflaumbaum,_W.-5] Beth-Hübner, M., Brandt, B., Rupp, R., Neumann, V., Eickmann, U., Lindner, G., Auras, S., Fröhlich, H.-P., Isringhausen, A. , Kraus, W., Pucknat, D., Pucknat, U., Neumeister, L., Seibel, J., Fauss, J., Brüning, T., Käfferlein, HU, Taeger, D., Weiß, T., Fritz, C., Breuer, D., Giesen, Y., Pflaumbaum, W .: Aromatic Amines A working aid in the determination of occupational diseases . DGUV / IFA, 2018, ISBN 3-86423-225-2 , p. 75 ( limited preview in Google Book search).

[Sigma-6] Data sheet 2-Amino-1-naphthalenesulfonic acid, 98% from Sigma-Aldrich , accessed on November 6, 2018 ( PDF ).

[Maximilian_Zander-7] Maximilian Zander: Polycyclic aromatic hydrocarbons and fullerenes . Springer-Verlag, 2013, ISBN 978-3-322-96707-7 , p. 195 ( limited preview in Google Book search).