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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/REAXYS Number:
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

signalword

Warning

hcodes

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

586.4 °F - closed cup

flash_point_c

308 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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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)
E H Ohlstein et al.
Life sciences, 46(3), 181-188 (1990-01-01)
The biosynthesis and modulation of the vasoconstrictor peptide endothelin was studied in the conditioned medium from cultured bovine pulmonary artery endothelial (BPAE) cells. Conditioned medium from cultured BPAE cells produced contraction of isolated rabbit aortic rings. Incubation of BPAE cells
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
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
Asha M D'Souza et al.
Organic letters, 13(3), 486-489 (2010-12-24)
A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient
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