CAS 118-48-9|ISATOIC ANHYDRIDE|2,4-dihydro-1H-3,1-benzoxazine-2,4-dione|1H-3,1-benzoxazine-2,4-dione|1H-benzo[d][1,3]oxazine-2,4-dione|衣托酸酐|3,1-Benzoxazine-2,4(1H)-dione|Anthranilic acid N-carbo...

General Information

Structure

Molecular Formula

C₈H₅NO₃

Molecular Mass

163.1302

Exact Mass

163.02694303

Charge

InChI

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

InChIKey

TXJUTRJFNRYTHH-UHFFFAOYSA-N

Canonic Smiles

O=c1oc(=O)c2c([nH]1)cccc2

Isomeric Smiles

O=c1[nH]c2c(cccc2)c(=O)o1

Calculated Properties

JChem

Acid pKa

9.395176

H Acceptors

H Donor

LogD (pH = 5.5)

1.4760556

LogD (pH = 7.4)

1.4719576

Log P

1.4761082

Molar Refractivity

41.8263

Polarizability

15.27678

Polar Surface Area

55.4

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

ISATOIC ANHYDRIDE1H-benzo[d][1,3]oxazine-2,4-dione衣托酸酐3,1-Benzoxazine-2,4(1H)-dioneAnthranilic acid N-carboxylic acid anhydrideIsatoic anhydride靛红酸酐N-羧鄰胺苯甲酐1,2-Dihydro-3,1-benzoxazine-2,4-dione2H-3,1-Benzoxazine-2,4(1H)-dione2-(Carboxyamino)benzoic Acid Cyclic AnhydrideNSC 104662Isatoic Acid Anhydride2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazineNSC 295551H-Benz[d][1,3]oxazine-2,4-dione4H-3,1-Benzoxazine-2,4(1H)-dione

IUPAC name

2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

IUPAC Traditional name

1H-3,1-benzoxazine-2,4-dione

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

EC Number

MDL Number

Beilstein Number

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05215507

MP Biomedicals Rare Chemical collection

Sigma Aldrich

I12808

Packaging
100, 500 g in poly bottle

58279

Other Notes
Review1; Reagent for 2-aminobenzoylations2

TRC

I777600

Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

Molecule Details

References

PubChem Literature

From Data Sources

• Khiav, B. et al.: Int. Arch. Allergy Immunol., 113, 291 (1982)

• Moorman, A.J. et al.: J. AM. Chem. Soc., 104, 6785 (1982)

• Shinogi, M. et al.: J. Pharmac. Sci., 74, 782 (1982)

• Susceptible to nucleophilic attack, normally at the "acid" 4-carbon. More hindered nucleophiles attack at the "carbamate" 2-carbon. In the presence of DMAP, attack is directed to C-4, giving anthranilic acid derivatives: Synthesis, 266 (1982). For reviews of the chemistry of isatoic anhydrides, including reactions with a wide range of nucleophiles and the formation of a variety of heterocyclic systems, see: Synthesis, 505 (1980); Adv. Heterocycl Chem., 28, 127 (1981).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

IUPAC Traditional name

1H-3,1-benzoxazine-2,4-dione

Registration numbers

CAS Number

PubChem CID

PubChem SID

EC Number

MDL Number

Beilstein Number

Molecule Details

MP Biomedicals Rare Chemical collection

Sigma Aldrich

I12808

Packaging
100, 500 g in poly bottle

58279

Other Notes
Review1; Reagent for 2-aminobenzoylations2

TRC

I777600

Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

References

PubChem Literature

From Data Sources

• Khiav, B. et al.: Int. Arch. Allergy Immunol., 113, 291 (1982)

• Moorman, A.J. et al.: J. AM. Chem. Soc., 104, 6785 (1982)

• Shinogi, M. et al.: J. Pharmac. Sci., 74, 782 (1982)

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:110550