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Merck
CN

I12808

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
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24895927
EC Number:
204-255-0
Beilstein/REAXYS Number:
136786
MDL number:
MFCD00006700

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InChI key

TXJUTRJFNRYTHH-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1Nc2ccccc2C(=O)O1

vapor density

5.6 (vs air)

assay

96%

mp

233 °C (dec.) (lit.)

Quality Level

100

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB0494
MKCQ5195
MKCG9203
MKCG9345
MKCC6235

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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
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-).
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)
L Servillo et al.
European journal of biochemistry, 213(1), 583-589 (1993-04-01)
A fluorescent tRNA derivative labeled at 3'-O position of the ultimate adenosine residue by reaction, under mild conditions, of tRNA with isatoic anhydride [3,1-benzoxazine-2,4(1H)-dione] was obtained. The labeling selectivity was determined by several criteria: digestion with RNase, followed by HPLC
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
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