Isatoic Anhydride

Isatoic Anhydride Basic information
Synthesis
Product Name:Isatoic Anhydride
Synonyms:1,2-Dihydro-3,1-benzoxazine-2,4-dione;2-(carboxyamino)-benzoicacicyclicanhydride;2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine;4H-3,1-Benzoxazin-2,4-(1H)-dion;4H-3,1-Benzoxazin-2,4(1H)-dion;Anthranilic acid, N-carboxy-, cyclic anhydride;Benzoic acid, 2-(carboxyamino)-, cyclic anhydride;Benzoicacid,2-(carboxyamino)-,cyclicanhydride
CAS:118-48-9
MF:C8H5NO3
MW:163.13
EINECS:204-255-0
Product Categories:Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;pharmacetical;118-48-9
Mol File:118-48-9.mol
Isatoic Anhydride Structure
Isatoic Anhydride Chemical Properties
Melting point 233 °C (dec.) (lit.)
Boiling point 290.19°C (rough estimate)
density 1,52 g/cm3
vapor density 5.6 (vs air)
refractive index 1.5510 (estimate)
Fp 308 °C
storage temp. Store below +30°C.
solubility 0.3g/l
form Powder
pka11.06±0.20(Predicted)
color Beige to brown
Water Solubility decomposes
Sensitive Moisture Sensitive
BRN 136786
LogP0.978 (est)
CAS DataBase Reference118-48-9(CAS DataBase Reference)
NIST Chemistry ReferenceIsatoic anhydride(118-48-9)
EPA Substance Registry System2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9)
Safety Information
Hazard Codes Xi
Risk Statements 36-43
Safety Statements 24-26-37
WGK Germany 1
RTECS DM3100000
3
Autoignition Temperature>600 °C
TSCA Yes
HS Code 29349990
Hazardous Substances Data118-48-9(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
ProviderLanguage
4H-3,1-Benzoxazine-2,4(1H)-dione English
ACROS English
SigmaAldrich English
ALFA English
Isatoic Anhydride Usage And Synthesis
Synthesis Isatoic Anhydride is synthesized from indole (9a) by stirring in a 4:1 mixture of  DMF/H2O for 16 h at room temperature. 
1 H NMR (DMSO-d6): δ11.73 (s, br., 1H),  7.92 (d, J = 7.8 Hz, 1H), 7.74 (t, J = 7.8 Hz, 1H), 7.26 (t, J = 7.8 Hz, 1H), 7.16 (d,  J = 7.8 Hz, 1H).

Chemical PropertiesBEIGE TO BROWN POWDER
UsesIsatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.
DefinitionA bicyclic molecule composed of a benzene ring attached at the oand mpositions to a heterocyclic ring. It forms useful anthranilic acid derivatives by reaction with hydrogen.
PreparationPhosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.
Flammability and ExplosibilityNonflammable
Purification MethodsRecrystallise it from EtOH or 95% EtOH (30mL/g) or dioxane (10mL/g) and dry it in a vacuum. [Wagner & Fegley Org Synth Coll Vol III 488 1955, Ben-Ishai & Katchalski J Am Chem Soc 74 3688 1952, UV: Zentmyer & Wagner J Org Chem 14 967 1949, Beilstein 27 II 299, 27III/IV 3330.]
5-NITROISATOIC ANHYDRIDE 6-CHLOROISATIN 5-Bromoisatoic anhydride 4-NITRO-ISATOIC ANHYDRIDE N-methylisatoic anhydride 5-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE N-ALLYLISATOIC ANHYDRIDE 6-CHLORO-2H-1,4-BENZOXAZINE-2,3(4H)-DIONE 3-OXIME 6-METHYL ISATINIC ANHYDRIDE 2H-1,4-benzoxazine-2,3(4H)-dione AKOS BBS-00002894 5-AMINOISATOIC ANHYDRIDE 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione 1-Benzyl-2H-3,1-benzoxazine-2,4(1H)-dione 6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione Isatoic Anhydride 4-CARBOXYLIC-ISATOIC ANHYDRIDE 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE

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