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184475-35-2

Basic Information
CAS No.: 184475-35-2
Name: Gefitinib
Article Data: 53
Cas Database
Molecular Structure:
Molecular Structure of 184475-35-2 (Gefitinib)
Formula: C22H24ClFN4O3
Molecular Weight: 446.909
Synonyms: N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine;ZD1839;4-(3-Chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline;Irressat;Gefitinib (JAN/USAN);4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-;ZD 1839;4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-;
EINECS: 643-034-7
Density: 1.322 g/cm3
Melting Point: 119-120 °C
Boiling Point: 586.8 °C at 760 mmHg
Flash Point: 308.7 °C
Solubility: N/A
Appearance: light-yellow crystalline powder
Hazard Symbols: Xi
Risk Codes: R36/37/38
Safety: 24/25
Transport Information: N/A
PSA: 68.74000
LogP: 4.28650
Synthetic route
367-21-5

3-chloro-4-fluorophenylamine

199327-59-8

4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol at 20℃;99%
In isopropyl alcohol at 80℃; for 0.533333h; Microwave irradiation;92%
With N,N,N,N,-tetramethylethylenediamine; nickel dichloride In tetrahydrofuran at 50℃; for 0.333333h; Concentration; Temperature; Reagent/catalyst;92.5%
367-21-5

3-chloro-4-fluorophenylamine

4-iodo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
In isopropyl alcohol Reflux;92.46%
367-21-5

3-chloro-4-fluorophenylamine

4-bromo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
In isopropyl alcohol Reflux;92.06%
7357-67-7

4-(3-chloropropyl)morpholine

184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 3h; Reagent/catalyst; Temperature;92%
With tetrabutylammomium bromide; sodium carbonate; potassium iodide In iso-butanol Reflux;90%
In N,N-dimethyl-formamide at 80 - 90℃; Concentration;88%
320366-66-3

4-(3-((4-chloro-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine

1435-48-9

1,3-dichloro-4-fluorobenzene

184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Reflux;91%

4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline dihydrochloride

184475-35-2

gefitinib

Conditions
ConditionsYield
With sodium hydroxide In water at 30 - 70℃; for 1.5h; pH=11 - 13;90.7%
957621-67-9

3-morpholinopropyl 4-methylbenzenesulfonate

184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.5%
675126-27-9

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

367-21-5

3-chloro-4-fluorophenylamine

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

184475-35-2

gefitinib

Conditions
ConditionsYield
Stage #1: 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile; N,N-dimethyl-formamide dimethyl acetal With acetic acid In toluene at 85 - 90℃; for 2h;
Stage #2: 3-chloro-4-fluorophenylamine With acetic acid In toluene at 75 - 85℃; for 2.5h; Inert atmosphere;
89.5%
1018895-28-7

methanesulfonic acid 3-morpholin-4-yl-propyl ester

184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.2%
958669-55-1

4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline

367-21-5

3-chloro-4-fluorophenylamine

184475-35-2

gefitinib

Conditions
ConditionsYield
With 3-chloro-4-fluoroaniline hydrochloride In isopropyl alcohol for 24h; Heating;85%
Downstream Products
199327-61-2
847949-49-9
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    Product Name: Gefitinib Synonyms: Gefitinib N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine;IRESSA;GEFITINIB;AKOS 91371;n-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine;N-(3

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Specification

1. Introduction of Gefitinib

Gefitinib is an light-yellow crystalline Powder. With the IUPAC Name of N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy) quinazolin-4-amine, it belongs to the Product Categories which include Active Pharmaceutical Ingredients; Gefitinib; Molecular Targeted Antineoplastic; Intermediates & Fine Chemicals; Pharmaceuticals; Pharmaceutical intermediate. Gefitinib is a drug used in the treatment of certain types of cancer.

2. Properties of Gefitinib

Gefitinib has the following datas: (1)Molar Volume: 337.7 cm3; (2)Polarizability: 47.09×10-24cm3; (3)Surface Tension: 55.2 dyne/cm; (4)Density: 1.322 g/cm3; (5)Flash Point: 308.7 °C; (6)Enthalpy of Vaporization: 87.63 kJ/mol; (7)Melting Point: 119-120 °C; (8)Boiling Point: 586.8 °C at 760 mmHg; (9)Vapour Pressure: 9.48E-14 mmHg at 25°C.

3. Structure Descriptors of Gefitinib

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
(2).InChI: InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)
(3).InChIKey: XGALLCVXEZPNRQ-UHFFFAOYSA-N