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Basic Information
CAS No.: 1480-19-9
Name: Fluanisone
Molecular Structure:
Molecular Structure of 1480-19-9 (Fluanisone)
Formula: C21H25 F N2 O2
Molecular Weight: 356.44
Synonyms: Butyrophenone,4'-fluoro-4-[4-(o-methoxyphenyl)-1-piperazinyl]- (6CI,7CI,8CI); 2028 MD;4-[4-(o-Methoxyphenyl)-1-piperazinyl]-p-fluorobutyrophenone;4'-Fluoro-4-[4-(o-methoxyphenyl)-1-piperazinyl]butyrophenone; Anti-Pica;Fluanison; Fluanisone; Haloanison; Haloanisone; MD 2028; NSC 170977; R 2028; R2167; Sedalande; p-Fluoro-g-[4-(o-methoxyphenyl)-1-piperazinyl]butyrophenone; g-(4-o-Methoxyphenylpiperazino)-4-fluorobutyrophenone
Density: 1.146g/cm3
Melting Point: 67.5-68.5°
Boiling Point: 511.8°Cat760mmHg
Flash Point: 263.3°C
Safety: Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of F− and NOx.
PSA: 32.78000
LogP: 3.62230
Synthetic route
857-62-5

Anisopirol

1480-19-9

fluanisone

Conditions
ConditionsYield
With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 3h; Inert atmosphere;92%
459-57-4

4-fluorobenzaldehyde

1480-19-9

fluanisone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: zinc / tetrahydrofuran / 0.17 - 0.25 h / 20 °C
1.2: 3 h / 0 °C
2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / Reflux
3.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C
3.2: 1 h / 0 °C
4.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
5.1: acetic acid / methanol / 1 h / 0 - 20 °C
5.2: 3 h / 0 - 20 °C
6.1: 10% Pd/C; hydrogen / methanol / 10 h / 20 °C
7.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
View Scheme
86718-78-7, 136185-86-9

1-(4-fluorophenyl)-3-buten-1-ol

1480-19-9

fluanisone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / Reflux
2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C
2.2: 1 h / 0 °C
3.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
4.1: acetic acid / methanol / 1 h / 0 - 20 °C
4.2: 3 h / 0 - 20 °C
5.1: 10% Pd/C; hydrogen / methanol / 10 h / 20 °C
6.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
View Scheme
1143515-07-4

1-[1-(benzyloxy)-but-3-enyl]-4-fluorobenzene

1480-19-9

fluanisone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C
1.2: 1 h / 0 °C
2.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
3.1: acetic acid / methanol / 1 h / 0 - 20 °C
3.2: 3 h / 0 - 20 °C
4.1: 10% Pd/C; hydrogen / methanol / 10 h / 20 °C
5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
View Scheme
1402042-55-0

4-(benzyloxy)-4-(4-fluorophenyl)-butan-1-ol

1480-19-9

fluanisone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
2.1: acetic acid / methanol / 1 h / 0 - 20 °C
2.2: 3 h / 0 - 20 °C
3.1: 10% Pd/C; hydrogen / methanol / 10 h / 20 °C
4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
View Scheme
1402042-56-1

4-(benzyloxy)-4-(4-fluorophenyl)-butanal

1480-19-9

fluanisone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / methanol / 1 h / 0 - 20 °C
1.2: 3 h / 0 - 20 °C
2.1: 10% Pd/C; hydrogen / methanol / 10 h / 20 °C
3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
View Scheme
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Chemistry

IUPAC Name: 1-(4-Fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-ium-1-yl]butan-1-one chloride 
Molecular Formula: C21H25FN2O2
Molecular Weight: 356.48
EINECS: 216-038-8
Density: 1.146g/cm3
Melting Point: 67.5–68.5°C
Boiling Point: 511.8°C at 760mmHg
Flash Point: 263.3°C
Properties: crystals 
Solubility: soluble in chloroform; sparingly soluble in methanol; sltly soluble in ether. practically insolublein water. 
Freely Rotating Bonds: 7
Polar Surface Area: 32.78 Å2
Index of Refraction: 1.557
Molar Refractivity: 100.25 cm3
Molar Volume: 310.9 cm3
Polarizability: 39.74× 10-24 cm3
Surface Tension: 42.1 dyne/cm
Enthalpy of Vaporization: 78.28 kJ/mol
Vapour Pressure: 1.38E-10 mmHg at 25°C
The Cas Register Number  of Haloanisone is 1480-19-9.The chemical synonyms of Haloanisone (CAS NO.1480-19-9) are 1-(4-Fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-one ; 1-Butanone, 1- (4-fluorophenyl)-4-[4-(2-methoxyphenyl)-1-piperazinyl]- ; 4-[4-(o-Methoxyphenyl)-1-piperazinyl]-p-fluorobutyrophenone ; 4'-Fluoro-4-[4-(o-methoxyphenyl)-1-piperazinyl]butyrophenone ; Butyrophenone, 4'-fluoro-4-[4- (o-methoxyphenyl)-1-piperazinyl]- ; 1-(4-Fluorophenyl)-4-[4-(2-methoxyphenyl)-1-piperazinyl]-1-butanone ; 1-(4-Fluoro-phenyl)-4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butan-1-one ; 1-(4-Fluoro-phenyl)-4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butan-1-one(fluanisone) ; 1-Butanone, 1-(4-fluorophenyl)-4-(4-(2-methoxyphenyl)-1-piperazinyl)- (9CI) ; 4-(4-(o-Methoxyphenyl)-1-piperazinyl)-p-fluorobutyrophenone ; 4'-Fluoro-4-(4-(o-methoxyphenyl)-1-piperazinyl)- butyrophenone ; 4'-Fluoro-4-(4-(o-methoxyphenyl)-1-piperazinyl)butyrophenone ; Anti-Pica ; Butyrophenone, 4'-fluoro-4-(4-(o-methoxyphenyl)-1-piperazinyl)- ; Fluanison ; Fluanisone dihydrochloride ; Fluanisone monohydrochloride ; Haloanison ; Metorin ; Sedalande .The molecular structure of Haloanisone (CAS NO.1480-19-9) is.

Uses

 Haloanisone (CAS NO.1480-19-9)is used as Antipsychotic and in the treatment of schizophrenia and mania.

Toxicity Data With Reference

1.    

orl-rat TDLo:132 mg/kg (15D preg):TER

    PJPPAA    Polish Journal of Pharmacology and Pharmacy. 32 (1980),199.
2.    

scu-rat LD50:420 mg/kg

    MDCHAG    Medicinal Chemistry: A Series of Monographs. 4 (2)(1967),199.
3.    

orl-mus LD50:550 mg/kg

    APPHAX    Acta Poloniae Pharmaceutica. 40 (1983),159.
4.    

ipr-mus LD50:200 mg/kg

    FRPSAX    Farmaco, Edizione Scientifica. 35 (1980),605.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of F− and NOx.

Specification

It is a typical antipsychotic and sedative of the butyrophenone chemical class.