Isatoic anhydride

Structural formula
General
Surname	Isatoic anhydride
other names	4 H -3,1-benzoxazine-2,4- (1 H ) -dione; 2,4-Dioxo-1,2-dihydro-3,1-benzoxazine; N -carboxyanthranilic anhydride;
Molecular formula	C 8 H 5 NO 3
Brief description	beige odorless solid
External identifiers / databases
EC number	204-255-0
ECHA InfoCard	100,003,869
PubChem	8359
ChemSpider	8056
DrugBank	DB11593
Wikidata	Q11286492
properties
Molar mass	163.13 g mol −1
Physical state	firmly
density	1.52 g cm −3
Melting point	230-232 ° C
solubility	very sparingly soluble in water (0.3 g l −1 at 20 ° C); insoluble in ethanol, benzene and chloroform;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 317-319
	P: 280-302 + 352-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isatoic anhydride is a chemical compound from the group of nitrogen-oxygen heterocycles with a keto group .

Extraction and presentation

Isatoic anhydride can be obtained by introducing phosgene into a solution of anthranilic acid in aqueous hydrochloric acid . This synthesis was first carried out by Erdmann in 1899. The first synthesis was carried out in 1883 by Paul Friedlaender .

properties

Isatoic anhydride is a flammable, moisture-sensitive, beige, odorless solid that is very sparingly soluble in water. It decomposes when heated above 350 ° C.

use

Isatoic anhydride is an intermediate for various applications. It is used in coatings and serves as a raw material for agro-active ingredients.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 118-48-9 in the GESTIS substance database of the IFA , accessed on June 29, 2015(JavaScript required) .
^ William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 42 ( limited preview in Google Book search).
↑ Entry on 4H-3,1-benzoxazine-2,4 (1H) -dione 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 .
^ Entry on isatoic anhydride in the Hazardous Substances Data Bank , accessed on June 29, 2015.
↑ T.kap : Isatoic anhydrides and their uses in heterocyclic synthesis , accessed June 29, 2015.
^ BASF: Isatoic anhydride , accessed June 29, 2015.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry for CAS no. 118-48-9 in the GESTIS substance database of the IFA , accessed on June 29, 2015(JavaScript required) .

[William_M._Haynes-2] William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 42 ( limited preview in Google Book search).

[CLP_100.003.869-3] Entry on 4H-3,1-benzoxazine-2,4 (1H) -dione 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 .

[HSDB-4] Entry on isatoic anhydride in the Hazardous Substances Data Bank , accessed on June 29, 2015.

[T._Kappe-5] T.kap : Isatoic anhydrides and their uses in heterocyclic synthesis , accessed June 29, 2015.

[6] BASF: Isatoic anhydride , accessed June 29, 2015.