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

• ChemBase ID: 110550
• Molecular Formular: C8H5NO3
• Molecular Mass: 163.1302
• Monoisotopic Mass: 163.02694303
• SMILES: O=c1[nH]c2c(cccc2)c(=O)o1
• Canonical SMILES: O=c1oc(=O)c2c([nH]1)cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
• IUPAC Traditional name: 1H-3,1-benzoxazine-2,4-dione
• Synonyms: 3,1-Benzoxazine-2,4(1H)-dione; Anthranilic acid N-carboxylic acid anhydride; Isatoic anhydride; 1H-benzo[d][1,3]oxazine-2,4-dione; ISATOIC ANHYDRIDE; 4H-3,1-Benzoxazine-2,4(1H)-dione; 2H-3,1-Benzoxazine-2,4(1H)-dione; 1,2-Dihydro-3,1-benzoxazine-2,4-dione; 1H-Benz[d][1,3]oxazine-2,4-dione; 2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine; 2-(Carboxyamino)benzoic Acid Cyclic Anhydride; Isatoic Acid Anhydride; NSC 104662; NSC 29555; N-羧鄰胺苯甲酐; 衣托酸酐; 靛红酸酐

Database IDs

• CAS Number: 118-48-9
• EC Number: 204-255-0
• MDL Number: MFCD00006700
• Beilstein Number: 136786
• PubChem SID: 162096513; 24895927
• PubChem CID: 8359

CALCULATED PROPERTIES

• Acid pKa: 9.395176
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4760556
• LogD (pH = 7.4): 1.4719576
• Log P: 1.4761082
• Molar Refractivity: 41.8263 cm^3
• Polarizability: 15.27678 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Brown Solid
• Melting Point: 233 °C (dec.)(lit.); 234-236°C (dec.); ca 237°C dec.
• Flash Point: 308 °C; 308°C(586°F); 586.4 °F
• Density: 1.520
• Vapor Density: 5.6 (vs air)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• RTECS: DM3100000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36-43
• Safety Statements: 24-26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319; H319-H317
• GHS Precautionary statements: P261-P280-P305+P351+P338-P302+P352-P321-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥94% (HPLC); 96%; 97%
• Grade: technical
• Empirical Formula (Hill Notation): C8H5NO3

DETAILS

MP Biomedicals - 05215507

MP Biomedicals Rare Chemical collection

Sigma Aldrich - I12808

Packaging
100, 500 g in poly bottle

Sigma Aldrich - 58279

Other Notes
Review1; Reagent for 2-aminobenzoylations2

Toronto Research Chemicals - 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

• Moorman, A.J. et al.: J. AM. Chem. Soc., 104, 6785 (1982)
• Shinogi, M. et al.: J. Pharmac. Sci., 74, 782 (1982)
• Khiav, B. et al.: Int. Arch. Allergy Immunol., 113, 291 (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).