5-Chloro-N-methylisatoic anhydride supplier

Name
6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione
EINECS 238-551-6
CAS No. 14529-12-5
Article Data28
CAS DataBase
Density 1.477 g/cm³
Solubility
Melting Point 113 °C
Formula C₉H₆ClNO₃
Boiling Point 346.94 °C at 760 mmHg
Molecular Weight 211.605
Flash Point 163.623 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 6-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione;6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione;N-Methyl-5-chloroisatoicanhydride;N-methyl-5-Chloro-isatoic anhydride;2H-3,1-Benzoxazine-2,4(1H)-dione,6-chloro-1-methyl-;
PSA 52.21000
LogP 1.14510

Synthetic route

: 4743-17-3
5-Chloroisatoic anhydride

: 74-88-4
methyl iodide

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
In ice-water; ISOPROPYLAMIDE	90%
With sodium carbonate In N,N-dimethyl-formamide	85.2%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	83%

: 201230-82-2
carbon monoxide

: 932-96-7
N-methyl(p-chloroaniline)

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate; potassium iodide; Trimethylacetic acid In acetonitrile at 60℃; under 760.051 Torr; regioselective reaction;	78%

: 4743-17-3
5-Chloroisatoic anhydride

: 74-83-9
methyl bromide

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
Stage #1: 5-Chloroisatoic anhydride With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methyl bromide In N,N-dimethyl-formamide for 18h;	72%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;

: 201230-82-2
carbon monoxide

: 698-69-1
4-chloro-N,N-dimethylaniline

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); oxygen; copper diacetate In N,N-dimethyl-formamide; toluene at 100℃;	71%
With dichloro bis(acetonitrile) palladium(II); oxygen; copper diacetate In N,N-dimethyl-formamide; toluene at 100℃; under 760.051 Torr; for 24h;	71%

: 541-41-3
chloroformic acid ethyl ester

: 77-78-1
dimethyl sulfate

: 635-21-2
5-chloroanthranilic acid

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 385653/, (iii) AcCl; Multistep reaction;

...Expand

: 4743-17-3
5-Chloroisatoic anhydride

CH3-Hal: CH3-Hal

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, 2 h, 2.) 8 h; Multistep reaction;

: 4743-17-3
5-Chloroisatoic anhydride

methyl halide: methyl halide

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
(i) NaH, AcNMe2, (ii) methyl halide; Multistep reaction;

: 60434-13-1
5-chloro-1-methylindoline-2, 3-dione

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;

: 65798-06-3, 17122-56-4
N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / 80 °C 2: NaH / N,N-dimethyl-acetamide / 20 °C 3: mCPBA / CH2Cl2 / 20 °C View Scheme

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

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / N,N-dimethyl-acetamide / 20 °C 2: mCPBA / CH2Cl2 / 20 °C View Scheme

: 106-47-8
4-chloro-aniline

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NH2OH*HCl; Na2SO4; aq. conc. HCl / Heating 2: H2SO4 / 80 °C 3: NaH / N,N-dimethyl-acetamide / 20 °C 4: mCPBA / CH2Cl2 / 20 °C View Scheme

: 635-21-2
5-chloroanthranilic acid

: 14529-12-5
6-chloro-N-methylisatoic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 20 - 100 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 4 h / Reflux 2: N,N-dimethyl-formamide / 18 h / 20 °C / Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 3.25 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 56-40-6
glycine

: 5973-28-4
7-chloro-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

Conditions

Conditions	Yield
Stage #1: 6-chloro-N-methylisatoic anhydride; glycine With acetic acid at 130℃; for 7h; Stage #2: With sodium hydroxide; water; sodium hydrogencarbonate pH=~ 9 - 10;	100%
With acetic acid at 130℃; for 7h;
With acetic acid at 130℃; for 7h;

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 105-53-3
diethyl malonate

: 52851-65-7
ethyl 6-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylate

Conditions

Conditions	Yield
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl acetamide at 20 - 90℃; for 0.5h; Stage #2: 6-chloro-N-methylisatoic anhydride In N,N-dimethyl acetamide at 20 - 110℃;	97%
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 6-chloro-N-methylisatoic anhydride In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;	30%

: 1459246-69-5
4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-6-(4-bromophenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;	93%

: 1459246-69-5
4-(4-bromophenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: C19H15BrClNO4

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;	93%

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-11-chloro-1-methyl-6-phenyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 4h;	87%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 4h; Schlenk technique; Inert atmosphere;	83%

: 1638152-34-7
4-(4-methylphenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-11-chloro-1-methyl-6-(p-tolyl)-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 8h;	87%

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: C19H16ClNO4

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 4h;	87%

: 100-36-7
N,N-diethylethylenediamine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 159619-29-1
5-chloro-N-[2-(diethylamino)ethyl]-2-methylaminobenzamide

Conditions

Conditions	Yield
In 1,4-dioxane at 60℃; for 2h;	85%

: 1459246-68-4
4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-11-chloro-6-(4-chlorophenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;	85%

: 1459246-67-3
4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-11-chloro-6-(4-methoxyphenyl)-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 6h;	85%

: 1459246-68-4
4-(4-chlorophenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: C19H15Cl2NO4

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 2h;	85%

: 1459246-67-3
4-(4-methoxyphenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: C20H18ClNO5

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 6h;	85%

: 100-63-0
phenylhydrazine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 6630-33-7
ortho-bromobenzaldehyde

: 1452386-56-9
2-(2-bromophenyl)-6-chloro-1-methyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
Stage #1: phenylhydrazine; 6-chloro-N-methylisatoic anhydride In acetonitrile Reflux; Stage #2: ortho-bromobenzaldehyde With toluene-4-sulfonic acid In acetonitrile at 81℃;	84%

...Expand

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 56-40-6
glycine

A: 72952-53-5
5-chloro-2-(methylamino)hippuric acid

B: 33280-14-7
5-chloro-2-methylamino-benzoic acid

Conditions

Conditions	Yield
With sodium carbonate In water	A 83.9% B 7%

...Expand

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 622-16-2
1,3-Diphenylcarbodiimide

: (Z)-6-chloro-1-methyl-3-phenyl-2-(phenylimino)-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; zinc In acetonitrile at 100℃; for 10h; Sealed tube; Inert atmosphere;	83%

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 104-78-9
diethylaminopropylamine

: 5-chloro-N-[3-(diethylamino)propyl]-2-methylamino benzamide

Conditions

Conditions	Yield
In 1,4-dioxane; ethyl acetate	81%
In 1,4-dioxane at 60℃; for 5h;	80%

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

petroleum ether-isopropanol-ammonia: petroleum ether-isopropanol-ammonia

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 5-chloro-2-methylamino-N-[2-(1-pyrrolidinyl)ethyl] benzamide

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; dichloromethane	80%

...Expand

: 93102-05-7
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 1261594-23-3
3-benzyl-7-chloro-1-methyl-3,4-dihydro-1H-benzo[d][1,3]diazepine-5(2H)-one

Conditions

Conditions	Yield
With lithium fluoride In acetonitrile at 35℃; for 3h; Inert atmosphere; Molecular sieve; Sonication;	76%

: 30125-76-9
1-(phenylmethyl)pyrrolidine-2,4-dione

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 2-benzyl-7-chloro-4-methyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline-1,9(4H)-dione

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 2h; Sealed tube; Inert atmosphere; Molecular sieve;	76%

: 2038-03-1
4-(2-AMINOETHYL)MORPHOLINE

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 92299-77-9
5-chloro-2-methylamino-N-<2-(4-morpholinyl)ethyl>-benzamide

Conditions

Conditions	Yield
In 1,4-dioxane for 2h; Ambient temperature;	75%

: 141-43-5
ethanolamine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 4927-76-8
5-Chlor-N-(2-hydroxy-aethyl)-2-methylamino-benzamid

Conditions

Conditions	Yield
In 1,4-dioxane at 60℃; for 1.5h;	74%

: 61-54-1
tryptamine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 3-chloro-14-methyl-8,13,13b,14-tetrahydro-7H-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5-one

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; trifluoroacetic anhydride In N,N-dimethyl acetamide at 100℃; for 5h;	74%

: 23451-62-9
dimethyl(prop-2-yn-1-yl)sulfonium bromide

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 6-chloro-1,2-dimethyl-3-(methylthio)quinolin-4(1H)-one

Conditions

Conditions	Yield
With dmap In acetonitrile at 60℃; for 5h;	70%

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: 7212-59-1
4,9-dihydro-6-methoxy-3H-pyrido[3,4-b]indole

: 1394329-48-6
C20H18ClN3O2

Conditions

Conditions	Yield
In dichloromethane at 45℃; for 6h;	69%

: 14173-39-8
p-chlorophenylalanine

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (S)-7-chloro-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Conditions

Conditions	Yield
With acetic acid for 18h; Reflux;	67%
With acetic acid for 16h; Reflux;	67%

: 4-(4-(benzyloxy)phenyl)-4-vinyl-1,3-dioxolan-2-one

: 14529-12-5
6-chloro-N-methylisatoic anhydride

: (Z)-6-(4-(benzyloxy)phenyl)-11-chloro-1-methyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azacycloundecine-2,9(1H)-dione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In ethyl acetate at 60℃; for 3h;	67%

5-Chloro-N-methylisatoic anhydride Chemical Properties

IUPAC Name: 6-Chloro-1-methyl-3,1-benzoxazine-2,4-dione
Canonical SMILES: CN1C2=C(C=C(C=C2)Cl)C(=O)OC1=O
InChI: InChI=1S/C9H6ClNO3/c1-11-7-3-2-5(10)4-6(7)8(12)14-9(11)13/h2-4H,1H3
InChIKey: FKTQNWWDMJDNHA-UHFFFAOYSA-N
Molecular Weight: 211.60184 [g/mol]
Molecular Formula: C₉H₆ClNO₃
XLogP3-AA: 1.8
H-Bond Donor: 0
H-Bond Acceptor: 3
EINECS: 238-551-6
Index of Refraction: 1.597
Molar Refractivity: 48.85 cm³
Molar Volume: 143.3 cm³
Surface Tension: 52.9 dyne/cm
Density: 1.476 g/cm³
Flash Point: 163.6 °C
Enthalpy of Vaporization: 59.12 kJ/mol
Boiling Point: 346.9 °C at 760 mmHg
Vapour Pressure: 5.57E-05 mmHg at 25 °C
Classification Code of 5-Chloro-N-methylisatoic anhydride (CAS NO.14529-12-5): Reproductive Effect

5-Chloro-N-methylisatoic anhydride Specification

5-Chloro-N-methylisatoic anhydride (CAS NO.14529-12-5), its Synonyms are 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl- ; 6-Chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione ; 6-Chloro-N-methyl IA .

Product Name

6-chloro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

Synthetic route

5-Chloro-N-methylisatoic anhydride Chemical Properties

5-Chloro-N-methylisatoic anhydride Specification

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