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I12808

Sigma-Aldrich

Isatoic anhydride

96%

Synonym(s):

3,1-Benzoxazine-2,4(1H)-dione, Anthranilic acid N-carboxylic acid anhydride

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About This Item

Empirical Formula (Hill Notation):
C8H5NO3
CAS Number:
118-48-9
Molecular Weight:
163.13
Beilstein:
136786
EC Number:
204-255-0
MDL number:
MFCD00006700
UNSPSC Code:
12162002
PubChem Substance ID:
24895927
NACRES:
NA.23

vapor density

5.6 (vs air)

Assay

96%

mp

233 °C (dec.) (lit.)

SMILES string

O=C1Nc2ccccc2C(=O)O1

InChI

1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)

InChI key

TXJUTRJFNRYTHH-UHFFFAOYSA-N

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Related Categories

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H319

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

586.4 °F - closed cup

Flash Point(C)

308 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jonathan J Goodall et al.
Chembiochem : a European journal of chemical biology, 3(1), 68-75 (2007-06-27)
The acyl-enzyme formed upon acylation of alpha-chymotrypsin with isatoic anhydride has been characterised by infrared spectroscopy. Acylation at pH 7 to yield the 2-aminobenzoyl-enzyme is rapid (k = 5.57x 10(-2)s(-1)), while deacylation is much slower (k =3.7 x 10(-5)10(-2) (s-).
P S Gravett et al.
The International journal of biochemistry, 23(10), 1101-1110 (1991-01-01)
1. Esterase E-I from Bitis gabonica was inactivated with irreversible inhibitors which included studies with a water-soluble carbodiimide, an affinity labelling peptide and a mechanism-based inactivator. 2. The reaction with 1-ethyl-3(3-dimethylaminopropyl)-carbodiimide was biphasic and the dominant part followed saturation kinetics.
Zheng-Hui Guan et al.
Journal of the American Chemical Society, 134(42), 17490-17493 (2012-10-12)
A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and
K Siva Kumar et al.
Organic & biomolecular chemistry, 10(15), 3098-3103 (2012-03-10)
A one-pot cascade reaction has been developed leading to the concurrent construction of six and five membered fused N-heterocyclic rings of indazolo[3,2-b]quinazolinones. The methodology involved the reaction of isatoic anhydride, a hydrazine and o-iodo benzaldehyde in the presence of Pd(PPh(3))(4)
M H Gelb et al.
Journal of medicinal chemistry, 29(4), 585-589 (1986-04-01)
Derivatives of isatoic anhydride were prepared and tested as inhibitors of serine proteases. A number of isatoic anhydrides with positively charged substituents irreversibly inactivated several trypsin-like enzymes and preferentially inactivated trypsin over chymotrypsin. Further selectivity was obtained by introduction of
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