Isatoic anhydride supplier

Name
4H-3,1-Benzoxazine-2,4(1H)-dione
EINECS 204-255-0
CAS No. 118-48-9
Article Data140
CAS DataBase
Density 1.402 g/cm³
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
Appearance beige to brown powder
Safety 24-26-37
Risk Codes 36-43
Molecular Structure
Hazard Symbols Xi
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;
PSA 63.07000
LogP 0.48130

Synthetic route

: 91-56-5
indole-2,3-dione

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium acetate In tetrahydrofuran at 60℃; for 16h;	90%

...Expand

: 487-89-8
Indole-3-carboxaldehyde

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With Oxone In water; N,N-dimethyl-formamide at 20℃;	85%

: 120-72-9
indole

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

: 64784-13-0, 482-89-3, 141901-19-1
indigo

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With Oxone In water; acetonitrile at 60℃; for 1h;	76%

: 5100-23-2
2-isocyanatobenzoyl chloride

: 100-58-3
phenylmagnesium bromide

A: 579-93-1
2-(Benzoylamino)benzoic Acid

B: 29670-64-2
N-(2-benzoylphenyl)benzamide

C: 118-48-9
isatoic anhydride

D: 1022-46-4
2-phenyl-4H-3,1-benzoxazin-4-one

Conditions

Conditions	Yield
In diethyl ether at 25 - 30℃; for 3h;	A 6% B 5% C 10% D 70%
In diethyl ether at 25 - 30℃; for 3h; other 2-Isocyanatobenzoyl chloride;	A 6% B 5% C 10% D 70%

...Expand

: 21282-65-5
2-[(morpholinocarbonyl)amino]benzoic acid

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With hydrogenchloride for 0.0333333h; Cyclization; Heating;	68%

: 201230-82-2
carbon monoxide

: 615-43-0
2-iodophenylamine

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With potassium phosphate; oxygen; palladium diacetate; potassium iodide; calcium chloride; copper dichloride; Trimethylacetic acid In acetonitrile at 100℃; under 2280.15 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent;	68%

: 118-92-3
anthranilic acid

: 503-38-8
trichloromethyl chloroformate

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With pyridine In dichloromethane; acetonitrile at 50℃;	63%
With N,N-dimethyl-aniline

: 124-38-9
carbon dioxide

: 183209-26-9
ortho-bromophenyl isocyanide

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
Stage #1: ortho-bromophenyl isocyanide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 1h; Further stages;	61%

: 1942-45-6
4-Octyne

: 201230-82-2
carbon monoxide

: 98952-64-8
N-ethoxycarbonyl-2-iodoaniline

A: 118-48-9
isatoic anhydride

B: 3,4-dipropyl-2(1H)-quinolinone

C: 2-oxo-3,4-dipropyl-2H-quinoline-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 24h;	A n/a B 47% C 18%

...Expand

: 487-89-8
Indole-3-carboxaldehyde

A: 118-48-9
isatoic anhydride

B: 479-41-4
indirubin

C: 13220-57-0
tryptanthrine

Conditions

Conditions	Yield
With Oxone In water; acetonitrile at 20℃; for 16h;	A 42% B 6% C 12%

...Expand

: 64784-13-0, 482-89-3, 141901-19-1
indigo

A: 118-48-9
isatoic anhydride

B: 13220-57-0
tryptanthrine

C: 91-56-5
indole-2,3-dione

Conditions

Conditions	Yield
With 1,2-Diiodoethane; sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.25h; Microwave irradiation;	A n/a B 26% C n/a

...Expand

: 85-44-9
phthalic anhydride

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With sodium azide; sulfuric acid

: 124840-74-0
4-oxo-4H-benzo[d][1,3]oxazine-2-carbonitrile

: 64-17-5
ethanol

A: 118-48-9
isatoic anhydride

B: 74-90-8
hydrogen cyanide

...Expand

: 271-58-9
anthranil

: 541-41-3
chloroformic acid ethyl ester

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
at 140℃; im Rohr;
at 120 - 140℃;

: 63254-88-6
2-(((benzyloxy)carbonyl)amino)benzoic acid

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With phosphorus tribromide

: 541-41-3
chloroformic acid ethyl ester

: 41470-93-3
2-((ethoxycarbonyl)amino)benzoic acid

: 118-48-9
isatoic anhydride

: 75-44-5
phosgene

: 118-92-3
anthranilic acid

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With hydrogenchloride
(i) ClSiMe3, Et3N, CH2Cl2, (ii) /BRN= 1098367/, benzene; Multistep reaction;
In hydrogenchloride for 1.5h;
In 1,4-dioxane at 20℃; for 1h;

: 75-36-5
acetyl chloride

: 41470-93-3
2-((ethoxycarbonyl)amino)benzoic acid

: 118-48-9
isatoic anhydride

: 41470-93-3
2-((ethoxycarbonyl)amino)benzoic acid

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With phosphorus tribromide

: 482-89-3
1H,1H'-2,2'-Biindolylidene-3,3'-dione

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
With ozone; ethyl acetate

: 34314-65-3
N-(trimethylsilyl)isatoic anhydride

: 118-48-9
isatoic anhydride

Conditions

Conditions	Yield
In ethanol

: 118-48-9
isatoic anhydride

: 2450-71-7
Propargylamine

: 4943-83-3
2-amino-N-(prop-2-yn-1-yl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;	100%
In N,N-dimethyl-formamide at 20℃; for 1h;	97%
In N,N-dimethyl-formamide at 40 - 45℃; for 4h;	90%

: 118-48-9
isatoic anhydride

: 147-85-3
L-proline

: 24919-40-2, 60269-66-1, 18877-34-4
(S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 160℃; for 4h;	100%
In dimethyl sulfoxide at 180℃; Condensation;	96%
In dimethyl sulfoxide at 100℃; for 4h;	95%

: 35161-71-8
N-methylpropargylamine

: 118-48-9
isatoic anhydride

: 2-amino-N-methyl-N-(prop-2-yn-1-yl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;	100%
In 1,4-dioxane for 3h; Reflux;	81%
In 1,4-dioxane at 100℃; for 3h;	81%
In 1,4-dioxane for 3h; Acylation; hydrolysis; Heating;	54%

: 56-91-7
p-aminomethylbenzoic acid

: 118-48-9
isatoic anhydride

: 503039-57-4
4-((2-aminobenzamido)methyl)benzoic acid

Conditions

Conditions	Yield
With triethylamine In water at 40℃; for 3h;	100%
With triethylamine In water	72%
With triethylamine In water	72%
With dmap; triethylamine In pyridine; N,N-dimethyl-formamide at 80℃; for 16h;	70.7%
In water at 20℃; for 2h; Green chemistry;

: 118-48-9
isatoic anhydride

: 4141-08-6
2-Amino-N-methylbenzamid

Conditions

Conditions	Yield
With methylamine In tetrahydrofuran; methanol	100%

: 118-48-9
isatoic anhydride

: 101620-78-4
1-(4-aminobutyl)-4-diphenylmethoxypiperidine

: 221539-51-1
2-amino-N-[4-(4-diphenylmethoxypiperidino)butyl]benzamide

Conditions

Conditions	Yield
	100%

: 118-48-9
isatoic anhydride

: 184780-41-4
4-aminomethyl-1-diphenylmethylpiperidine

: 2-amino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Conditions

Conditions	Yield
In dichloromethane	100%

: 118-48-9
isatoic anhydride

: trans-4-aminomethyl-cyclohexanecarboxylic acid methyl ester

: methyl 4-((2-aminobenzamido)methyl)cyclohexan-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃;	100%
With potassium carbonate In acetonitrile at 70℃;	100%

: 118-48-9
isatoic anhydride

: 479-27-6
naphthalene-1,8-diamine

: N,N′-(naphthalene-1,8-diyl)bis(2-aminobenzamide)

Conditions

Conditions	Yield
In water at 60℃; for 1h;	100%
In water at 60℃; for 1h;	100%

: 118-48-9
isatoic anhydride

: 144222-22-0
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate

: tert-butyl 4-[(2-aminobenzamide)methyl]piperidine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 80℃; for 2h;	100%

: 118-48-9
isatoic anhydride

: 6940-76-7
1-iodo-3-chloro-propane

: 57384-63-1
1-(3-chloro-propyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions

Conditions	Yield
Stage #1: isatoic anhydride With sodium hydride In N,N-dimethyl-formamide Stage #2: 1-iodo-3-chloro-propane In N,N-dimethyl-formamide	100%

: 118-48-9
isatoic anhydride

: 124-40-3
dimethyl amine

: 6526-66-5
2-amino-N,N-dimethylbenzamide

Conditions

Conditions	Yield
In ethanol; water at 25℃; for 2h;	99.4%
With dmap In acetonitrile at 0 - 20℃; for 26h; Schlenk technique; Inert atmosphere;

: 118-48-9
isatoic anhydride

: 107-19-7
propargyl alcohol

: 90923-99-2
propargyl anthranilate

Conditions

Conditions	Yield
With sodium hydride Reflux;	99.3%
With sodium hydride In mineral oil for 2h; Reflux; Inert atmosphere;	82%
With pyridine; sodium hydride 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 4 h; Multistep reaction;

: 118-48-9
isatoic anhydride

: 122-51-0
orthoformic acid triethyl ester

: 111108-39-5
1-(2-aminoethyl)-4-(2-ethoxyphenyl)piperazine

: 111108-20-4
3-[2-[4-(2-ethoxyphenyl)-1-piperazinyl]-ethyl]-4(3H)-quinazolone

Conditions

Conditions	Yield
	99.2%

...Expand

: 118-48-9
isatoic anhydride

: 104-94-9
4-methoxy-aniline

: 20878-54-0
2-amino-N-(4-methoxyphenyl)benzamide

Conditions

Conditions	Yield
In water at 80℃; for 9h; Large scale;	99%
In toluene for 4h; Reflux;	96%
In ethyl acetate	92%

: 118-48-9
isatoic anhydride

: 100-63-0
phenylhydrazine

: 30086-49-8
2-amino-N'-phenylbenzohydrazide

Conditions

Conditions	Yield
With aluminum potassium sulfate dodecahydrate In ethanol Reflux;	99%
for 0.5h; Neat (no solvent); Heated to melting;	82%
With acetic acid In ethanol for 2h; Reagent/catalyst; Reflux;	82%

: 118-48-9
isatoic anhydride

: 74-89-5
methylamine

: 4141-08-6
2-Amino-N-methylbenzamid

Conditions

Conditions	Yield
In tetrahydrofuran; water for 2.5h;	99%
In 1,4-dioxane for 0.333333h;	97%
In tetrahydrofuran; methanol at 20℃; for 16h;	97.8%

: 118-48-9
isatoic anhydride

: 49802-15-5
diethyl (4-chlorophenyl)phosphoramidate

: 2400-95-5
3-(4-chlorophenyl)-1H,3H-quinazolin-2,4-dione

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; benzene at 80℃; for 5h;	99%

: 118-48-9
isatoic anhydride

: 91-56-5
indole-2,3-dione

: 13220-57-0
tryptanthrine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 100℃; for 0.0333333h; Reagent/catalyst; Temperature; Ionic liquid; Microwave irradiation; Inert atmosphere;	99%
With cobalt(III) meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin chloride In ethanol; water at 20℃; for 3h; Reagent/catalyst; Solvent; Green chemistry;	95%
With triethylamine In toluene at 110℃; for 6h;	95%

: 118-48-9
isatoic anhydride

: 459-73-4
GlyOEt*HCl

: 5973-34-2
(2-aminobenzoylamino)acetic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 18h; Reflux;	99%
In pyridine

: 118-48-9
isatoic anhydride

: 147-85-3
L-proline

: 18877-34-4, 24919-40-2, 60269-66-1
1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 4h;	99%
In N,N-dimethyl-formamide for 2h; Heating;

: 118-48-9
isatoic anhydride

: 100-52-7
benzaldehyde

: 62-53-3
aniline

: 21132-01-4
2,3-diphenyl-2,3-dihydro-1H-quinazolin-4-one

Conditions

Conditions	Yield
With Cu-CNTs nanocomposite In neat (no solvent) for 0.0833333h; Time; Microwave irradiation;	99%
With FeIII(acac)3 complex supported on silica In water at 80℃; for 1.5h; Green chemistry;	98%
With cobalt supported on multi-walled carbon nanotubes In ethanol at 40℃; for 0.1h; Reagent/catalyst; Solvent; Sonication; Green chemistry;	97%

...Expand

: 118-48-9
isatoic anhydride

: 1122-91-4
4-bromo-benzaldehyde

: 2,3-dihydro-2-(4-bromophenyl)quinazolin-4(1H)-one

Conditions

Conditions	Yield
With ammonium acetate; iodine at 110℃; for 0.0833333h;	99%
With ammonium acetate In ethanol for 0.2h; Microwave irradiation; Green chemistry;	96%
With ammonium acetate; L-proline In water at 100℃; for 0.133333h; Microwave irradiation;	93%

: 118-48-9
isatoic anhydride

: 123-08-0
4-hydroxy-benzaldehyde

: 107920-18-3
2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With ammonium acetate at 115℃; for 0.0833333h;	99%
With ammonium acetate In water at 80℃; for 1h; Green chemistry;	95%
With titanium silicon oxide; ammonium acetate In water at 100℃; for 2h; Green chemistry;	94%

: 118-48-9
isatoic anhydride

: 5122-94-1
4-biphenylboronic acid

: biphenyl-4-yl 2-aminobenzoate

Conditions

Conditions	Yield
With N-methylcyclohexylamine; tris-(dibenzylideneacetone)dipalladium(0); oxygen; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 60℃; for 24h;	99%

: 118-48-9
isatoic anhydride

: 1564241-91-3
C8H15NO2

: 1564241-97-9
ethyl (E)-5-(2-aminobenzamido)-3-methylpent-2-enoate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 24h; Reflux;	99%

: 118-48-9
isatoic anhydride

: 631-61-8
ammonium acetate

: 66-77-3
1-naphthaldehyde

: 31785-60-1
2,3-dihydro-2-(naphthalene-1-yl)quinazolin-4(1H)-one

Conditions

Conditions	Yield
With 3,3′-(butane-1,4-diyl)bis(1,2-dimethyl-1H-imidazole-3-ium) dibromide for 0.05h; Microwave irradiation;	99%

...Expand

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^-24cm³; (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

Product Name

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

Synthetic route

Isatoic anhydride Chemical Properties

Isatoic anhydride Consensus Reports

Isatoic anhydride Specification

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