Naphthalic anhydride

Structural formula
General
Surname	Naphthalic anhydride
other names	1 H , 3 H -naphtho [1,8- cd ] pyran-1,3-dione ( IUPAC ); 1,8-naphthalic anhydride;
Molecular formula	C 12 H 6 O 3
Brief description	beige powder
External identifiers / databases
EC number	201-380-2
ECHA InfoCard	100.001.256
PubChem	6693
Wikidata	Q424800
properties
Molar mass	198.18 g mol −1
Physical state	firmly
Melting point	269-276 ° C
boiling point	422 ° C
solubility	slightly soluble in water: 0.1 g l −1 (23 ° C); easily soluble in alcohol and ether; soluble in dimethylformamide;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 319-315-317-335
	P: 260-280-302 + 352
Toxicological data	12,300 mg kg −1 ( LD 50 , rat , oral ) ; > 2,030 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naphthalic anhydride is a chemical compound from the group of cyclic carboxylic acid anhydrides .

Extraction and presentation

Naphthalic anhydride by oxidation of acenaphthene prepared: in the vapor phase with air at 460 ° to 650 ° C to vanadium pentoxide - catalysts or in a solution in acetic acid at 100 to 150 ° C in the presence of cobalt - manganese - or bromide - ions .

properties

Naphthalic anhydride is a beige powder that is sparingly soluble in water, but readily soluble in ethanol and ether .

use

Naphthalic anhydride is used as intermediate for the preparation of imides and imide derivatives, in particular imidazole - dyes and optical brighteners used. It also acts as a herbicide safener , reducing the susceptibility of the crop to acetolactate synthase inhibitors such as B. sulfonylureas , lowers.

Individual evidence

↑ ^a ^b data sheet 1,8-Naphthalic anhydride from Sigma-Aldrich , accessed on September 11, 2010 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f ^g ^h Toxicological evaluation of naphthalic anhydride (PDF) at the professional association for raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
↑ ^a ^b ^c Entry on naphthalene-1,8-dicarboxylic acid anhydride in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Joanna Davies, John C. Caseley, Owen TG Jones, Michael Barrett, Nicholas D. Polge: Mode of action of naphthalic anhydride as a safener for the herbicide AC 263222 in maize . In: Pesticide Science . tape 52 , no. 1 , January 1998, pp. 29-38 ( PDF ).

[Sigma-1] ta sheet 1,8-Naphthalic anhydride from Sigma-Aldrich , accessed on September 11, 2010 ( PDF ).

[bgc-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Toxicological evaluation of naphthalic anhydride (PDF) at the professional association for raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

[GESTIS-3] Entry on naphthalene-1,8-dicarboxylic acid anhydride in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[4] Joanna Davies, John C. Caseley, Owen TG Jones, Michael Barrett, Nicholas D. Polge: Mode of action of naphthalic anhydride as a safener for the herbicide AC 263222 in maize . In: Pesticide Science . tape 52 , no. 1 , January 1998, pp. 29-38 ( PDF ).