| Identification | More | [Name]
4H-3,1-Benzoxazine-2,4(1H)-dione | [CAS]
118-48-9 | [Synonyms]
1,2-dihydro-4h-3,1-benzoxazine-2,4-dione
1,4-DIHYDRO-2H-3,1-BENZOXAZIN-2,4-DIONE
1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
2H-3,1-BENZOXAZINE-2,4(1H)-DIONE
3,1-BENZOXAZINE-2,4(1H)-DIONE
4H-3,1-Benzoxazine-2,4(1H)-dione
ANTHRANILIC ACID N-CARBOXYLIC ACID ANHYDRIDE
BENZOXAZINEDIONE
ISATOIC ANHYDRIDE
ISATOLC ANHYDRIDE
LABOTEST-BB LT00053651
N-CARBOXYANTHRANILIC ACID CYCLIC ANHYDRIDE
TIMTEC-BB SBB003928
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 | [EINECS(EC#)]
204-255-0 | [Molecular Formula]
C8H5NO3 | [MDL Number]
MFCD00006700 | [Molecular Weight]
163.13 | [MOL File]
118-48-9.mol |
| Chemical Properties | Back Directory | [Definition]
A 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. | [Appearance]
BEIGE TO BROWN POWDER | [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 | [pka]
11.06±0.20(Predicted) | [color ]
Beige to brown | [Water Solubility ]
decomposes | [Sensitive ]
Moisture Sensitive | [BRN ]
136786 | [LogP]
0.978 (est) | [CAS DataBase Reference]
118-48-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Isatoic anhydride(118-48-9) | [EPA Substance Registry System]
118-48-9(EPA Substance) |
| Questions And Answer | Back Directory | [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).
|
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S24:Avoid contact with skin .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37:Wear suitable gloves . | [WGK Germany ]
1
| [RTECS ]
DM3100000
| [F ]
3 | [Autoignition Temperature]
>600 °C | [TSCA ]
Yes | [HS Code ]
29349990 | [Hazardous Substances Data]
118-48-9(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
BEIGE TO BROWN POWDER | [Uses]
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. | [Preparation]
Phosphorus 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 Explosibility]
Nonflammable | [Purification Methods]
Recrystallise 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.] |
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