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)

Flash point:

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

2H-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

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

MSDS

• Language:English Provider:4H-3,1-Benzoxazine-2,4(1H)-dione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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 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.

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.

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

Non flammable

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.]

Isatoic Anhydride(118-48-9)Related Product Information

• 6-METHYL ISATINIC ANHYDRIDE
• N-methylisatoic anhydride
• 4-NITRO-ISATOIC ANHYDRIDE
• Isatoic Anhydride
• 5-Bromoisatoic anhydride
• 6-CHLOROISATIN
• 3-[2-(Diethylamino)ethyl]-2H-1,3-benzoxazine-2,4(3H)-dione
• 5-Fluoroisatonic anhydride
• 6-Fluoroisatoic anhydride
• 4-Chloro-isatoic anhydride
• 2 H-1,3-BENZOXAZINE-2,4(3 H)-DIONE
• 6-Chloro-4H-3,1-benzoxazine-2(1H),4-dione,6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione,6-chloro-4h-3,1-benzoxazine-2,4(1h)-dione
• 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
• 1-Benzyl-2H-3,1-benzoxazine-2,4(1H)-dione
• 6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione
• 4-CARBOXYLIC-ISATOIC ANHYDRIDE
• 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione
• N-ALLYLISATOIC ANHYDRIDE