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15362-40-0

Basic Information
CAS No.: 15362-40-0
Name: 1-(2,6-Dichlorophenyl)indolin-2-one
Article Data: 30
Molecular Structure:
Molecular Structure of 15362-40-0 (1-(2,6-Dichlorophenyl)indolin-2-one)
Formula: C14H9Cl2NO
Molecular Weight: 278.138
Synonyms: 2-Indolinone,1-(2,6-dichlorophenyl)- (8CI);1-(2,6-Dichlorophenyl)-2-indolinone;1-(2,6-Dichlorophenyl)oxindole;N-(2,6-Dichlorophenyl)-2-indolinone;NSC 621845;
EINECS: 239-399-3
Density: 1.432 g/cm3
Melting Point: 115-119°C
Boiling Point: 488.6 ºC at 760 mmHg
Flash Point: 249.3 ºC
Safety: 24/25
PSA: 20.31000
LogP: 4.27920
Synthetic route
83281-94-1

1-(2,6-dichlorophenyl)-3-(methylthio)oxindole

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With zinc In acetic acid for 4h; Heating;97%
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;94%
With thionyl chloride In dichloromethane; ethyl acetate at 50℃; for 2h; Concentration; Temperature;92%
With hydrogenchloride In acetonitrile at 78.85℃; for 5h; Rate constant; Kinetics; Mechanism; energy data: ΔH(activ.), ΔS(activ.); ΔE(activ.)var. amount of acetonitrile, var. temp.;
2916-31-6

2,2-dimethyl-1,3-dioxolane

15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

A

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

B

5-(2,6-dichloro-phenyl)-6,6-dimethyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol Cyclization;A n/a
B 93%
15307-93-4

N-phenyl-2,6-dichloroaniline

79-04-9

chloroacetyl chloride

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
Stage #1: N-phenyl-2,6-dichloroaniline; chloroacetyl chloride at 100℃; for 3h;
Stage #2: With aluminum (III) chloride at 100℃; for 1h; Temperature;
89%
126-39-6

2-ethyl-2-methyl-1,3-dioxolane

15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

A

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

B

5-(2,6-dichloro-phenyl)-6-ethyl-6-methyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol Cyclization;A n/a
B 84%
15307-79-6

diclofenac sodium

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With sodium hydride; Phenoxyacetyl chloride In tetrahydrofuran for 18h; Inert atmosphere;84%
Stage #1: diclofenac sodium With hydrogenchloride; water for 0.166667h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran for 3h;
47%
With sodium hydroxide In water at 123℃; for 0.5h; pH=8.41; Activation energy; Kinetics; Product distribution; Further Variations:; pH-values; Temperatures;1.7%
3644-56-2

2-chloro-N-(2,6-dichlorophenyl)acetamide

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With aluminium trichloride 1.) 145-150 deg C, 2.) 162-168 deg C, 2 h;81.3%

1-(2',6'-dichlorophenyl)-3-hydroxymethylene-2-indolinone

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With quinoline for 1h; Heating;78%
15308-01-7

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

Conditions
ConditionsYield
With aluminium trichloride at 160℃; for 2h;75.4%
With aluminum (III) chloride at 160℃; for 2h;62%
With aluminum (III) chloride at 160℃; for 2h;
With triethylamine hydrochloride-aluminum trichloride at 20 - 60℃; for 4.5h; Reagent/catalyst;
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

100-79-8

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

A

15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

B

1528769-06-3

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;A 21%
B 74%
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    1-(2,6-Dichlorophenyl)-2-indolinone

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    Appearance Colorless to brownish crystalline powder Assay,HPLC 98.5%-101.0% Impurity Individual impurity: 0.3% max Total impurities: 0.5% max Melting point 124℃-129℃ Loss on drying 0.5% max Residue on ignition 0.2% max Package:1kg/foil

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Specification

The 1-(2,6-Dichlorophenyl)-2-indolinone is an organic compound with the formula C14H9Cl2NO. The IUPAC name of this chemical is 1-(2,6-dichlorophenyl)-3H-indol-2-one. With the CAS registry number 15362-40-0, it is also named as 1,3-Dihydro-1-(2,6-dichlorophenyl)-2H-indol-2-one. The classification code is Drug / Therapeutic Agent.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3; (4)ACD/LogD (pH 7.4): 3; (5)ACD/BCF (pH 5.5): 112.37; (6)ACD/BCF (pH 7.4): 112.37; (7)ACD/KOC (pH 5.5): 1022.02; (8)ACD/KOC (pH 7.4): 1022.02; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.66; (13)Molar Refractivity: 71.74 cm3; (14)Molar Volume: 194.1 cm3; (15)Polarizability: 28.44×10-24 cm3; (16)Surface Tension: 56.3 dyne/cm; (17)Enthalpy of Vaporization: 75.47 kJ/mol; (18)Vapour Pressure: 1.07E-09 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 2; (21)Exact Mass: 277.006119; (22)MonoIsotopic Mass: 277.006119; (23)Topological Polar Surface Area: 20.3; (24)Heavy Atom Count: 18; (25)Complexity: 326.

Preparation of 1-(2,6-Dichlorophenyl)-2-indolinone: It can be obtained by 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide. This reaction needs reagent AlCl3 at temperature of 160 °C. The reaction time is 2 hours. The yield is 75.4%.

Uses of 1-(2,6-Dichlorophenyl)-2-indolinone: It is used as intermediates for drug diclofenac. And it also can react with 6-methoxy-2,3,4,5-tetrahydro-pyridine to get 1-(2,6-dichlorophenyl)-3-(piperidin-2-ylidene)indolin-2-one. This condensation reaction reacts by heating. The reaction time is 1.75 hours. The yield is 93.8%.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1cccc(Cl)c1N3c2ccccc2CC3=O
2. InChI:InChI=1/C14H9Cl2NO/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(17)18/h1-7H,8H2 
3. InChIKey:JCICIFOYVSPMHG-UHFFFAOYAO

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 unreported 1200mg/kg (1200mg/kg)   Pharmaceutical Chemistry Journal Vol. 21, Pg. 275, 1987.