5-Chloroisatoic anhydride supplier

Name
5-Chloroisatoic anhydride
EINECS 225-255-7
CAS No. 4743-17-3
Article Data45
CAS DataBase
Density 1.54 g/cm³
Solubility
Melting Point 300 °C (dec.)(lit.)
Formula C₈H₄ClNO₃
Boiling Point
Molecular Weight 197.578
Flash Point
Transport Information
Appearance
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Isatoicanhydride, 5-chloro- (6CI);5-Chloroisatoic anhydride;6-Chloro-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione;6-Chloro-1H-benzo[d][1,3]oxazine-2,4-dione;6-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione;6-Chloro-2H-3,1-dihydrobenzoxazine-2,4-dione;NSC 139890;NSC 75847;
PSA 63.07000
LogP 1.13470

Synthetic route

: 201230-82-2
carbon monoxide

: 635-21-2
5-chloroanthranilic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate; potassium iodide In acetonitrile at 60℃; under 760.051 Torr; for 4h;	99%

: 32315-10-9
bis(trichloromethyl) carbonate

: 635-21-2
5-chloroanthranilic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 4h; Reflux;	98%
In 1,2-dichloro-ethane for 3.25h; Reflux;	98%
In 1,2-dichloro-ethane at 80℃;	97%

: 2148-56-3
2-chloro-6-aminobenzoic acid

: 75-36-5
acetyl chloride

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-aminobenzoic acid With chloroformic acid ethyl ester In 1,4-dioxane for 1h; Heating / reflux; Stage #2: acetyl chloride In 1,4-dioxane at 50℃; for 10h;	97%

: 635-21-2
5-chloroanthranilic acid

: 503-38-8
trichloromethyl chloroformate

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; for 4h; Heating / reflux;	92%

: 118-48-9
isatoic anhydride

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
With chlorine In acetic acid at 80℃; for 1h;	85%

: 51108-30-6
4-chloro-1H-isoindole-1,3(2H)-dione

: 117-21-5
3-chlorophthalic anhydride

: 126-71-6
triisobutyl phosphate

: 5329-14-6
aminosulfonic acid

A: 4743-17-3
5-Chloroisatoic anhydride

B: 63497-60-9
8-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione

Conditions

Conditions	Yield
In water; formamide

...Expand

: 541-41-3
chloroformic acid ethyl ester

: 635-21-2
5-chloroanthranilic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
With triethylamine at 20 - 100℃; Inert atmosphere;

: 635-21-2
5-chloroanthranilic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / acetonitrile / 2 h / 20 °C 2: 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 0.17 h / 20 °C View Scheme

: 2-(tert-butoxycarbonylamino)-5-chlorobenzoic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
Stage #1: 2-(tert-butoxycarbonylamino)-5-chlorobenzoic acid With 2-chloro-1-methyl-pyridinium iodide In acetonitrile at 20℃; for 0.166667h; Stage #2: With hydrogenchloride In water; acetonitrile

: 535-80-8
3-chlorobenzoate

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride; nitric acid / 20 °C 2: hydrogen; palladium on activated charcoal / 20 °C 3: dichloromethane / 80 °C View Scheme

: 2516-95-2
5-chloro-2-nitrobenzoic acid

: 4743-17-3
5-Chloroisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / 20 °C 2: dichloromethane / 80 °C View Scheme

: 1072-98-6
5-chloro-2-pyridylamine

: 4743-17-3
5-Chloroisatoic anhydride

: (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide

Conditions

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran; toluene	100%
With potassium hexamethylsilazane In tetrahydrofuran; toluene	100%
With potassium hexamethylsilazane In tetrahydrofuran; toluene	100%
With potassium hexamethylsilazane In tetrahydrofuran; toluene	99%
With potassium hexamethylsilazane In tetrahydrofuran; toluene	99%

: 1072-98-6
5-chloro-2-pyridylamine

: 4743-17-3
5-Chloroisatoic anhydride

: 229343-30-0
2-amino-5-chloro-N-(5-chloro-pyridin-2-yl)-benzamide

Conditions

Conditions	Yield
Stage #1: 5-chloro-2-pyridylamine With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃;	100%
Stage #1: 5-chloro-2-pyridylamine With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃;	99%
Stage #1: 5-chloro-2-pyridylamine With dmap; potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; Inert atmosphere; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃; for 10h; Inert atmosphere;

: 4743-17-3
5-Chloroisatoic anhydride

: 57-14-7
1,1-dimethylhydrazine

: 87296-80-8
1-(5-chloro-2-aminobenzoyl)-2,2-dimethylhydrazine

Conditions

Conditions	Yield
With dmap In 1,2-dimethoxyethane at 45 - 50℃; for 3h;	98%
In 1,2-dimethoxyethane
With triethylamine In pyridine for 15h; Heating;	79 g

: 4743-17-3
5-Chloroisatoic anhydride

: 5584-15-6
5-chloroanthranilic acid hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate Ambient temperature;	97%
With hydrazine hydrate	85%
With hydrazine In water at 20℃; for 4.5h;	83%

: 627-37-2
N-methyl-N-allylamine

: 4743-17-3
5-Chloroisatoic anhydride

: 210241-75-1
2-amino-5-chloro-N-methyl-N-(2-propenyl)benzamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.0833333h; microwave irradiation;	97%
In N,N-dimethyl-formamide for 3h; Heating;	69%

: 4743-17-3
5-Chloroisatoic anhydride

: 124-41-4
sodium methylate

: 5202-89-1
4-chlorobenzenesulfonyl chloride

Conditions

Conditions	Yield
In methanol for 3h; Reflux;	97%

: 4743-17-3
5-Chloroisatoic anhydride

: 64-17-5
ethanol

: 130408-01-4
ethyl 5-chloroanthranilate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride Ambient temperature;	96%

: 4743-17-3
5-Chloroisatoic anhydride

: 459-46-1
4-Fluorobenzyl bromide

: 6-chloro-1-(4-fluoro-benzyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions

Conditions	Yield
Stage #1: 5-Chloroisatoic anhydride With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 1h; Stage #2: 4-Fluorobenzyl bromide In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;	96%

: 4743-17-3
5-Chloroisatoic anhydride

: 762-42-5
dimethyl acetylenedicarboxylate

: 17454-31-8
C14H14ClNO6

Conditions

Conditions	Yield
With sodium methylate In methanol for 2h; Reflux;	96%

: 4743-17-3
5-Chloroisatoic anhydride

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 42558-54-3
Methyl 4-methyl-3-oxopentanoate

: C15H13ClF3NO5S

Conditions

Conditions	Yield
Stage #1: 5-Chloroisatoic anhydride; Methyl 4-methyl-3-oxopentanoate With sodium hydride In N,N-dimethyl acetamide at 0 - 120℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;	95%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 126-81-8
dimedone

: 55579-87-8
7-chloro-3,3-dimethyl-3,4-dihydro-acridine-1,9(2H,10H)-dione

Conditions

Conditions	Yield
Stage #1: dimedone With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.1h; Stage #2: 5-Chloroisatoic anhydride In N,N-dimethyl-formamide at 90 - 100℃; for 4h;	95%

: 4743-17-3
5-Chloroisatoic anhydride

: 2393-23-9
4-methoxy-benzylamine

: 119-67-5
o-carboxybenzaldehyde

: 3-chloro-6-(4-methoxybenzyl)-6,6a-dihydroisoindolo[2,1-a]quinazolin-5,11-dione

Conditions

Conditions	Yield
With acetic acid at 80℃; for 0.75h; Reagent/catalyst; Sonication;	95%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 62-53-3
aniline

: 119-67-5
o-carboxybenzaldehyde

: 3-chloro-6-phenyl-6,6a-dihydroisoindolo[2,1-a] quinazoline-5,11-dione

Conditions

Conditions	Yield
With acetic acid at 80℃; for 0.5h; Reagent/catalyst; Sonication;	95%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 106-47-8
4-chloro-aniline

: 119-67-5
o-carboxybenzaldehyde

: 3-chloro-6-(4-chlorophenyl)-6,6a-dihydroisoindolo[2,1-a]quinazolin-5,11-dione

Conditions

Conditions	Yield
With acetic acid at 80℃; for 0.5h; Reagent/catalyst; Sonication;	95%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 100-52-7
benzaldehyde

: 62-53-3
aniline

: 6-chloro-2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With FeIII(acac)3 complex supported on silica In water at 80℃; for 4h; Green chemistry;	95%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 80℃; for 0.25h; Microwave irradiation; Sealed tube; Green chemistry;	85%
With [PyPS]3PW12O40 In neat (no solvent) at 80℃; for 0.25h; Microwave irradiation; Sealed tube;	85%
With 1-(3-sulfopropyl)pyridinium phosphotungstate at 90℃; for 1h; Microwave irradiation;	80%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 104-87-0
4-methyl-benzaldehyde

: 62-53-3
aniline

: C21H17ClN2O

Conditions

Conditions	Yield
With FeIII(acac)3 complex supported on silica In water at 80℃; for 4h; Green chemistry;	95%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 95-54-5
1,2-diamino-benzene

: 82096-44-4
2‑chloro‑5H‑dibenzo[b,e][1,4]diazepin‑11(10H)‑one

Conditions

Conditions	Yield
With acetic acid In water at 100℃; for 2.5h;	94%

: 4743-17-3
5-Chloroisatoic anhydride

: 17630-76-1
5-chloroindole 2,3-dione

: 1443051-85-1
2,8-dichloroindolo[2,1-b]quinazoline-6,12-dione

Conditions

Conditions	Yield
With cobalt(III) meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin chloride In ethanol; water at 20℃; for 3h; Green chemistry;	94%

: 4743-17-3
5-Chloroisatoic anhydride

: 2450-71-7
Propargylamine

: 4943-81-1
2-amino-5-chloro-N-(prop-2-yn-1-yl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	94%
In N,N-dimethyl-formamide at 25℃;

: 4743-17-3
5-Chloroisatoic anhydride

: 496-72-0
4-methyl-1,2-diaminobenzene

: 1241385-90-9
2-chloro-8-methyl-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one

Conditions

Conditions	Yield
With acetic acid In water at 110℃; for 2h;	93%

: 1072-97-5
5-bromo-2-pyridylamine

: 4743-17-3
5-Chloroisatoic anhydride

: (2-amino-5-bromophenyl)-N-(5-chloro(2-pyridyl))carboxamide

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-pyridylamine With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃;	92%

: 4743-17-3
5-Chloroisatoic anhydride

: 104-88-1
4-chlorobenzaldehyde

: 62-53-3
aniline

: C20H14Cl2N2O

Conditions

Conditions	Yield
With FeIII(acac)3 complex supported on silica In water at 80℃; for 5h; Green chemistry;	92%

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

: 5202-85-7
2-Amino-5-chlorobenzamide

Conditions

Conditions	Yield
With ammonia In tetrahydrofuran at 0 - 20℃;	91%
With ammonium hydroxide for 4h; Ambient temperature;	88%
With ammonia In tetrahydrofuran Ambient temperature;	81%

: 7154-73-6
1-(2-aminoethyl)pyrrolidine

: 4743-17-3
5-Chloroisatoic anhydride

: 159794-23-7
2-amino-5-chloro-N-[2-(1-pyrrolidinyl)ethyl]benzamide

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane	91%
With sodium hydroxide In 1,4-dioxane; ethyl acetate	91%
In 1,4-dioxane at 60℃; for 2h;	85%

: 4743-17-3
5-Chloroisatoic anhydride

: 100-36-7
N,N-diethylethylenediamine

: 30646-50-5
2-amino-5-chloro-N-[2-(diethylamino)ethyl] benzamide

Conditions

Conditions	Yield
In 1,4-dioxane at 60℃; for 2h;	91%
In 1,4-dioxane at 20℃; for 0.75h;

5-Chloroisatoic anhydride Specification

The 5-Chloroisatoic anhydride, with CAS registry number 4743-17-3, belongs to the following product category: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts. It has the systematic name of 6-chloro-2H-3,1-benzoxazine-2,4(1H)-dione. What's more, its EINECS is 225-255-7.

Physical properties of 5-Chloroisatoic anhydride: (1)ACD/LogP: 1.58; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.58; (4)ACD/LogD (pH 7.4): 1.578; (5)ACD/BCF (pH 5.5): 9.348; (6)ACD/BCF (pH 7.4): 9.308; (7)ACD/KOC (pH 5.5): 172.369; (8)ACD/KOC (pH 7.4): 171.636; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 55.4 Å²; (13)Index of Refraction: 1.601; (14)Molar Refractivity: 43.925 cm³; (15)Molar Volume: 128.285 cm³; (16)Polarizability: 17.413×10^-24cm³; (17)Surface Tension: 54.477 dyne/cm.

Preparation: this chemical can be prepared by 5-chloro-indole-2,3-dione. This reaction will need reagent chromium trioxide, glacial acetic acid.

When you are using this chemical, please be cautious about it as the following:
The 5-Chloroisatoic anhydride irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc2c(cc1Cl)c(=O)oc(=O)[nH]2
(2)InChI: InChI=1/C8H4ClNO3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,(H,10,12)
(3)InChIKey: MYQFJMYJVJRSGP-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C8H4ClNO3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,(H,10,12)
(5)Std. InChIKey: MYQFJMYJVJRSGP-UHFFFAOYSA-N

Product Name

5-Chloroisatoic anhydride

Synthetic route

5-Chloroisatoic anhydride Specification

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