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99199-90-3

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Basic Information
CAS No.: 99199-90-3
Name: 6-Fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran
Article Data: 9
Molecular Structure:
Molecular Structure of 99199-90-3 (6-Fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran)
Formula: C11H11FO2
Molecular Weight: 194.206
Synonyms: 2H-1-Benzopyran,6-fluoro-3,4-dihydro-2-oxiranyl- (9CI);6-fluoro-3,4-dihydro-2h-1-benzopyran-2-oxiranyl;6-fluoro-2-oxiranyl-3, 4-dihydro-2h-1-benzopyran,enterprise standard;luoro-3,4-dihydro-2h-1-benzopyran-2-oxaranyl(for nebivolol);
EINECS: 1312995-182-4
Density: 1.299 g/cm3
Boiling Point: 291.741 °C at 760 mmHg
Flash Point: 137.798 °C
PSA: 21.76000
LogP: 1.91810
Related products
Synthetic route
409346-73-2

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde

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trimethylsulphonium iodide

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide cooling;
Stage #2: 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde In dimethyl sulfoxide at 20℃; for 1h;		100%
1017878-67-9

2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2yl)ethanol

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: 2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2yl)ethanol With sodium hydroxide In water; isopropyl alcohol at 0℃; for 1.5h; Inert atmosphere;
Stage #2: With acetic acid In water; isopropyl alcohol; toluene		96%
With sodium hydroxide In dichloromethane; water at -10 - 20℃; for 2.66667h;
409346-73-2

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde

1774-47-6

trimethylsulfoxonium iodide

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.5h;
Stage #2: 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde In dichloromethane; dimethyl sulfoxide at 20 - 25℃; for 1h;		90%
With sodium hydride In dimethyl sulfoxide at 20 - 25℃; for 1h;84%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide at 20 - 40℃; for 1.5h;
Stage #2: 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde In dimethyl sulfoxide at 20 - 40℃; for 1.5h;
1322623-11-9

1-(6-fluorochroman-2-yl)ethane-1,2-diol

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: 1-(6-fluorochroman-2-yl)ethane-1,2-diol With sodium hydride In tert-butyl methyl ether; dimethyl sulfoxide at 50℃; for 1h; Inert atmosphere;
Stage #2: With p-toluenesulfonyl chloride In tert-butyl methyl ether for 1h; Reagent/catalyst; Solvent; Inert atmosphere;		90%

2-bromo-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2yl)ethanol

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;83%
99199-60-7

6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Et3N; ClCOOEt / tetrahydrofuran / 10 h / 20 °C
1.2: 90 percent / NaBH4 / tetrahydrofuran; H2O / 5 h / 20 °C
2.1: 78 percent / pyridinium chloroformate/SiO2 / CH2Cl2 / 1.5 h / 20 °C
3.1: NaH / dimethylsulfoxide / cooling
3.2: 100 percent / dimethylsulfoxide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate; sulfuric acid / diethyl ether; tetrahydrofuran / 0.75 h / 0 - 35 °C
1.2: pH 7
2.1: sodium hydrogencarbonate / iodine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0.17 h / 20 °C
2.2: 24 h / 20 - 25 °C
3.1: sodium hydride / dimethyl sulfoxide / 0.5 h
3.2: 1 h / 20 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran; diethyl ether / 0.5 h / 0 - 35 °C
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; iodine / dichloromethane; water / 24 h / 20 °C
3: sodium hydride / dimethyl sulfoxide / 1 h / 20 - 25 °C
View Scheme
99199-59-4

6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 percent / H2 / Pd/C / acetic acid / 70 - 80 °C / 15001.2 Torr
2.1: Et3N; ClCOOEt / tetrahydrofuran / 10 h / 20 °C
2.2: 90 percent / NaBH4 / tetrahydrofuran; H2O / 5 h / 20 °C
3.1: 78 percent / pyridinium chloroformate/SiO2 / CH2Cl2 / 1.5 h / 20 °C
4.1: NaH / dimethylsulfoxide / cooling
4.2: 100 percent / dimethylsulfoxide / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen / 5%-palladium/activated carbon / tetrahydrofuran / 45 - 55 °C / 3000.3 Torr
2.1: n-butyllithium / hexane; tetrahydrofuran / -85 - -75 °C
2.2: -80 - 0 °C
3.1: ethanol; sodium tetrahydroborate / 2 h / 0 °C / Inert atmosphere
4.1: sodium hydroxide / isopropyl alcohol; water / 1.5 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogen / 5%-palladium/activated carbon / tetrahydrofuran / 45 - 55 °C / 3000.3 Torr
2.1: n-butyllithium / hexane; tetrahydrofuran / -85 - -75 °C
2.2: -80 - -70 °C
2.3: 2 h / Reflux
View Scheme
99199-62-9

(6-fluoro-3,4-dihydro-2H-chromene-2-yl)methanol

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 78 percent / pyridinium chloroformate/SiO2 / CH2Cl2 / 1.5 h / 20 °C
2.1: NaH / dimethylsulfoxide / cooling
2.2: 100 percent / dimethylsulfoxide / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / iodine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0.17 h / 20 °C
1.2: 24 h / 20 - 25 °C
2.1: sodium hydride / dimethyl sulfoxide / 0.5 h
2.2: 1 h / 20 - 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; iodine / dichloromethane; water / 24 h / 20 °C
2: sodium hydride / dimethyl sulfoxide / 1 h / 20 - 25 °C
View Scheme
874649-82-8

(-)-(R)-methyl 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylate

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / -85 - -75 °C
1.2: -80 - 0 °C
2.1: ethanol; sodium tetrahydroborate / 2 h / 0 °C / Inert atmosphere
3.1: sodium hydroxide / isopropyl alcohol; water / 1.5 h / 0 °C / Inert atmosphere
View Scheme
874649-82-8

(-)-(R)-methyl 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylate

74-97-5

chlorobromomethane

99199-90-3

6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran

Conditions
ConditionsYield
Stage #1: (-)-(R)-methyl 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylate; chlorobromomethane With n-butyllithium In tetrahydrofuran; hexane at -85 - -75℃;
Stage #2: With borane In tetrahydrofuran; hexane at -80 - -70℃;
Stage #3: With water; sodium hydroxide In tetrahydrofuran; hexane for 2h; Reflux;
Raw Materials
409346-73-2
99199-59-4
874649-82-8
99199-60-7
99199-62-9
2181-42-2
1774-47-6
74-97-5
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Chemistry

Molecular Structure of 2H-1-Benzopyran,6-fluoro-3,4-dihydro-2-(2-oxiranyl)- (CAS NO.99199-90-3):

CAS: 99199-90-3
Empirical Formula: C11H11FO2
Molecular Weight: 194.2022
ACD/LogP: 2.43
of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 2
ACD/LogD (pH 7.4): 2
ACD/BCF (pH 5.5): 36
ACD/BCF (pH 7.4): 36
ACD/KOC (pH 5.5): 450
ACD/KOC (pH 7.4): 450
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 21.76 Å2
Index of Refraction: 1.568
Molar Refractivity: 48.899 cm3
Molar Volume: 149.448 cm3
Surface Tension: 49.327 dyne/cm
Density: 1.299 g/cm3
Flash Point: 137.798 °C
Enthalpy of Vaporization: 50.991 kJ/mol
Boiling Point: 291.741 °C at 760 mmHg
Vapour Pressure: 0.003 mmHg at 25°C

Specification

 2H-1-Benzopyran,6-fluoro-3,4-dihydro-2-(2-oxiranyl)-, with CAS number of 99199-90-3, can be called luoro-3,4-dihydro-2h-1-benzopyran-2-oxaranyl(for nebivolol) ; 6-fluoro-3,4-dihydro-2h-1-benzopyran-2-oxaranyl ; 6-fluoro-3,4-dihydro-2-oxiranyl-2h-1-benzopyran ; 6-fluoro-2-oxiranyl-3, 4-dihydro-2h-1-benzopyran,enterprise standard ; 6-fluoro-3,4-dihydro-2-(2-oxiranyl)-2h-1-benzopyran ; 6-fluoro-3,4-dihydro-2h-1-benzopyran-2-oxiranyl .