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Isatoic anhydride

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Name

Isatoic anhydride

EINECS 204-255-0
CAS No. 118-48-9 Density 1.402 g/cm3
PSA 63.07000 LogP 0.48130
Solubility decomposes in water Melting Point 233 °C (dec.)(lit.)
Formula C8H5NO3 Boiling Point 290.19°C (rough estimate)
Molecular Weight 179.132 Flash Point 308 °C
Transport Information N/A Appearance beige to brown powder
Safety 24-26-37 Risk Codes 36-43
Molecular Structure Molecular Structure of 118-48-9 (4H-3,1-Benzoxazine-2,4(1H)-dione) Hazard Symbols IrritantXi
Synonyms

Isatoicanhydride (6CI);1,2-Dihydro-3,1-benzoxazine-2,4-dione;1H-Benz[d][1,3]oxazine-2,4-dione;1H-Benzo[d][1,3]oxazin-2,4-dione;1H-Benzo[d][1,3]oxazine-2,4-dione;2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine;3,1-Benzoxazine-2,4(1H)-dione;Benzoic acid, 2-(carboxyamino)-, cyclic anhydride;Isatoic acid anhydride;NSC104662;NSC 29555;

Article Data 140

Isatoic anhydride Synthetic route

91-56-5

indole-2,3-dione

118-48-9

isatoic anhydride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h; Inert atmosphere; Photolysis;100%
With tert.-butylhydroperoxide In water at 100℃; for 2h; Green chemistry;90%
With diphenyl diselenide; dihydrogen peroxide In N,N-dimethyl-formamide; acetonitrile at 25℃; for 8h; Solvent; Temperature; Reagent/catalyst; Time; Baeyer-Villiger Ketone Oxidation; Schlenk technique; Green chemistry;88%
32315-10-9

bis(trichloromethyl) carbonate

118-92-3

anthranilic acid

118-48-9

isatoic anhydride

Conditions
ConditionsYield
In tetrahydrofuran at 45℃; for 12h;100%
In 1,2-dichloro-ethane for 3.25h; Reflux;96%
In tetrahydrofuran for 4h; Reflux;95%
201230-82-2

carbon monoxide

118-92-3

anthranilic acid

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate; potassium iodide In acetonitrile at 60℃; under 760.051 Torr; for 4h; Catalytic behavior; Reagent/catalyst;99%
124-38-9

carbon dioxide

31162-13-7

2-azidobenzoic acid

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; triphenylphosphine In acetonitrile at 60℃; under 760.051 Torr; for 24h; Solvent; Temperature;99%
124-38-9

carbon dioxide

201230-82-2

carbon monoxide

615-43-0

2-iodophenylamine

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); cesium acetate In tetrahydrofuran at 60℃; for 16h;90%
487-89-8

Indole-3-carboxaldehyde

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With Oxone In water; N,N-dimethyl-formamide at 20℃;85%
120-72-9

indole

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With Oxone In water; N,N-dimethyl-formamide at 20℃; for 16h; Solvent;83%
541-41-3

chloroformic acid ethyl ester

118-92-3

anthranilic acid

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With triethylamine at 20 - 100℃; for 22.17h; Inert atmosphere;78%
1225068-05-2

2-(1H-imidazol-1-yl)-1H-indole

118-48-9

isatoic anhydride

Conditions
ConditionsYield
With Oxone In nitromethane at 100℃;78%

2-(6'-chloro-7'-methyl-1',1'-dioxo-2,6-dioxo-1,2,5,6-tetrahydro-2'H-spiro[benzo[d][1,3,7]oxadiazocine]-4,3'-[(1,4,2-benzodithiazine)]-1-ylcarbonyl)phenylcarbamic acid

A

118-48-9

isatoic anhydride

B

3-amino-6-chloro-8-methyl-1,4,2-benzodithiazine-1,1-dioxide

Conditions
ConditionsYield
Stage #1: 2-(6'-chloro-7'-methyl-1',1'-dioxo-2,6-dioxo-1,2,5,6-tetrahydro-2'H-spiro[benzo[d][1,3,7]oxadiazocine]-4,3'-[(1,4,2-benzodithiazine)]-1-ylcarbonyl)phenylcarbamic acid With water; sodium hydroxide at 20℃; for 30h;
Stage #2: With hydrogenchloride; water pH=6;
A 46%
B 76%

Isatoic anhydride Chemical Properties

;

Isatoic anhydride Consensus Reports

Reported in EPA TSCA Inventory.

Isatoic anhydride Specification

The Isatoic acid anhydride, with its cas register number 118-48-9, has its systematic name of 2H-3,1-benzoxazine-2,4(1H)-dione. This is a kind of white prismatic crystal and is soluble in ethanol and 1,4-dioxygenhexacyclo. Besides, its product categories are including aromatic carboxylic acids, amides, anilides, anhydrides & salts. What's more, it is sensitive chemically.

The characteristics of this chemical are as following: (1)ACD/LogP: 0.91; (2)ACD/LogD (pH 5.5): 0.9; (3)ACD/LogD (pH 7.4): 0.9; (4)ACD/BCF (pH 5.5): 2.87; (5)ACD/BCF (pH 7.4): 2.87; (6)ACD/KOC (pH 5.5): 73.98; (7)ACD/KOC (pH 7.4): 73.97; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)Polar Surface Area: 46.61; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 39.02 cm3; (13)Molar Volume: 116.3 cm3; (14)Polarizability: 15.47 ×10-24 cm3; (15)Surface Tension: 51.3 dyne/cm; (16)Density: 1.402 g/cm3; (17)Exact Mass 163.026943; (18)MonoIsotopic Mass 163.026943; (19)Topological Polar Surface Area 55.4; (20)Heavy Atom Count 12; (21)Complexity 226.

The production method of this chemical is as below: This chemical could be made from the reaction when o-aminobenzoic acid meets with carbonyl chloride. Firstly, dissolve the o-aminobenzoic acid in hot water and concentrated sulfuric acid, and then still the phosgene while stirring till Isatoic Anhydride separate out immediately; Secondly, when the reaction begins to exothermal, adjust the stilling rate of phosgene, while keep the temp. no higher than 50℃; Thirdly, continue to still phosgene for about 2-4h, till the absorbing speed begin to slow down; Lastly, dry the products in the air and then dry to 100℃ to get the products.

As for its usage,  it is widely applied in many ways. It could be used as the organic synthesis; It could be used as the material of pharmaceutic, pesticide and dyeing, and then it is also the important intermediate of Bentazon.

When you deal with this chemical, you should be very cautious. Firstly, this chemical may cause inflammation to the skin or other mucous, and may cause sensitisation by skin contact. Therefore, you should take the following instructions while using this chemical. Wear suitable gloves, and then avoid contact with skin. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.   

In addition, you could convert the following datas into the molecular structure:
SMILES:O=C1OC(=O)Nc2ccccc12
InChI:InChI=1/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)
InChIKey:TXJUTRJFNRYTHH-UHFFFAOYAD

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