2H-1,3-Benzoxazine-2,4(3H)-dione Chemical Properties

Melting point:

228-232 °C(lit.)

Density 

1.402±0.06 g/cm3(Predicted)

vapor pressure 

0.73-1.27Pa at 89.94-107.94℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO : ≥ 40 mg/mL (245.20 mM)

form 

Solid

pka

9.16±0.20(Predicted)

color 

White to off-white

Merck 

13,1879

InChI

InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)12-8(11)9-7/h1-4H,(H,9,10,11)

InChIKey

OAYRYNVEFFWSHK-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2C(=O)NC1=O

LogP

0.78-0.88 at 20℃

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

DM3110000

HS Code 

2934999090

2H-1,3-Benzoxazine-2,4(3H)-dione Usage And Synthesis

Chemical Properties

Off-white to light brown crystalline powder

Uses

analgesic

Definition

ChEBI: Carsalam is a benzoxazine.

General Description

Kinetic studies of the alkaline hydrolysis of 2H-1,3-benzoxazine-2,4(3H)-dione (carsalam) were conducted and reaction was found to be of fractional order with respect to [OH^-].

Synthesis

2H-1,3-Benzoxazine-2,4(3H)-dione was prepared according to the procedure of Hoback, Crum and Carroll. To a solution of 411 g. (3. 0 moles) salicylamide in 483 ml. (6.0 moles) of anhydrous pyridine at 0℃ was added slowly with stirring 572 ml. (6.0 moles) of ethyl chlorocarbonate. The resulting orange solution was refluxed for 5 hr. and poured into 2L of ice water. The filtered product was washed twice with 0.5L of water and recrystallized three times from acetone-ethanol (50: 50), giving white needles 2H-1,3-Benzoxazine-2,4(3H)-dione (83% yield), m.p. 227.5-228.5° (lit. 12), m.p. 227-228°, which gave no coloration with ethanolic ferric chloride[1].

References

[1] J. D. Crum, J. A. Franks Jr. “The chemistry of heterocycles. III. 2H-1,3-benzoxazine-2,4(3H)-dione and Some 3-substituted derivatives.??.” Journal of Heterocyclic Chemistry 2 1 (1965): 37–40.

2H-1,3-Benzoxazine-2,4(3H)-dione(2037-95-8)Related Product Information

• 3-[2-(Diethylamino)ethyl]-2H-1,3-benzoxazine-2,4(3H)-dione
• 6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione,6-Chloro-4H-3,1-benzoxazine-2(1H),4-dione,6-chloro-4h-3,1-benzoxazine-2,4(1h)-dione
• 7-METHOXY-1,3-BENZOXAZINE-2,4-DIONE
• Isatoic Anhydride
• N-methylisatoic anhydride
• 6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione
• 2H-1,3-Benzoxazine-2,4(3H)-dione
• 6-BROMO-2H-BENZO[E][1,3]OXAZINE-2,4(3H)-DIONE
• 8-Hydroxy-2H-1,3-benzoxazine-2,4(3H)-dione
• 6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione
• 3-Methyl-2H-1,3-benzoxazine-2,4(3H)-dione
• 2H-1,4-BENZOXAZINE-2,3(4H)-DIONE 3-OXIME
• 6-METHYL-2H-1,4-BENZOXAZINE-2,3(4H)-DIONE 3-OXIME
• 6-CHLORO-2H-1,4-BENZOXAZINE-2,3(4H)-DIONE 3-OXIME
• 5-Nitro-2H-3,1-benzoxazine-2,4(1H)-dione
• 7-Methyl-2H-1,3-benzoxazine-2,4(3H)-dione
• 5-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE
• 2H-1,4-benzoxazine-2,3(4H)-dione