58279
Isatoic anhydride
technical, ≥94% (HPLC)
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:
Molecular Weight:
163.13
EC Number:
204-255-0
UNSPSC Code:
12162002
PubChem Substance ID:
Beilstein/REAXYS Number:
136786
MDL number:
vapor density
5.6 (vs air)
grade
technical
assay
≥94% (HPLC)
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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Other Notes
Review; Reagent for 2-aminobenzoylations
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M.C. Venuti
Synthesis, 266-266 (1982)
G.M. Coppola
Synthesis, 505-505 (1980)
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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