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127264-14-6

Basic Information
CAS No.: 127264-14-6
Name: 5-(2-Bromoethyl)-2,3-dihydrobenzofuran
Article Data: 19
Molecular Structure:
Molecular Structure of 127264-14-6 (5-(2-Bromoethyl)-2,3-dihydrobenzofuran)
Formula: C10H11BrO
Molecular Weight: 227.101
Synonyms: 2,3-dihydro-5-(2-bromoethyl)benzofuran;
EINECS: 603-191-4
Density: 1.459 g/cm3
Melting Point: 65-67 °C
Boiling Point: 287.7 °C 760 mmHg
Flash Point: 113.8°C
Appearance: off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 22
PSA: 9.23000
LogP: 2.55890
Synthetic route
87776-76-9

5-(2-hydroxyethyl)-2,3-dihydrobenzofuran

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 63h;84%
With phosphorus tribromide In chloroform Reflux;75.9%
73%
151427-19-9

2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Stage #1: 2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one With sodium tetrahydroborate In tetrahydrofuran at 5 - 10℃; for 1h; Inert atmosphere;
Stage #2: With aluminum (III) chloride In tetrahydrofuran at 45 - 50℃; for 4h; Inert atmosphere;
74%
943034-50-2

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
With sodium bromide In acetone for 48h; Heating / reflux;
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C
1.2: 6 h / 0 - 5 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere
2.2: 4 h / 45 - 50 °C / Inert atmosphere
View Scheme
496-16-2

2,3-Dihydrobenzofuran

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.5 h / 0 - 5 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C
2.2: 6 h / 0 - 5 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere
3.2: 4 h / 45 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 10 °C
1.2: 10 - 20 °C
2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
3.1: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 10 °C
1.2: 10 - 20 °C
2.1: water; sodium hydroxide / 20 °C
3.1: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
4.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
5.1: phosphorus tribromide / chloroform / Reflux
View Scheme
64089-34-5

2-chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran / 10 h / -5 - 0 °C
2: sodium bromide / acetone / 48 h / Heating / reflux
View Scheme
79002-49-6

ethyl 2( 2,3-dihydro-1-benzofuran-5-yl)oxoacetate

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water; sodium hydroxide / 20 °C
2: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
3: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
4: phosphorus tribromide / chloroform / Reflux
View Scheme

C10H7O4(1-)*Na(1+)

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
3: phosphorus tribromide / chloroform / Reflux
View Scheme
69999-16-2

2,3-dihydrobenzofuran-5-acetic acid

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
2: phosphorus tribromide / chloroform / Reflux
View Scheme
156-38-7

4-hydroxyphenylacetate

127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 50 - 80 °C
2: toluene-4-sulfonic acid / Reflux; Large scale
3: polyphosphoric acid / toluene / 105 - 110 °C
4: sodium hydroxide; water / methanol / 25 - 30 °C
5: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
6: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
7: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 7 steps
1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 50 - 80 °C
2: toluene-4-sulfonic acid / Reflux; Large scale
3: polyphosphoric acid / toluene / 105 - 110 °C
4: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 65 - 70 °C / 3040.2 - 3800.26 Torr
5: sodium hydroxide; water / methanol / 25 - 60 °C
6: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
7: phosphorus tribromide / chloroform / Reflux
View Scheme
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133099-07-7
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Chemistry

IUPAC Name: 5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran
Synonyms of 5-(2-Bromoethyl)-2,3-dihydrobenzofuram (CAS NO.127264-14-6): 2,3-Dihydro-5-(2-bromoethyl)benzofuran ; 5-(2-Bromo ethyl)-2,3-dihydro benzofuran
CAS NO: 127264-14-6
Molecular Formula: C10H11BrO
Molecular Weight: 227.10
Molecular Structure:
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: Å2
Index of Refraction: 1.592
Molar Refractivity: 52.7 cm3
Molar Volume: 155.5 cm3
Surface Tension: 46.7 dyne/cm
Density: 1.459 g/cm3
Flash Point: 113.8 °C
Enthalpy of Vaporization: 50.57 kJ/mol
Boiling Point: 287.7 °C at 760 mmHg
Vapour Pressure: 0.00424 mmHg at 25°C 
Melting Point: 65-67°C 
Appearance: Off-White Powder
SMILES: BrCCc1cc2CCOc2cc1
InChI: InChI=1/C10H11BrO/c11-5-3-8-1-2-10-9(7-8)4-6-12-10/h1-2,7H,3-6H2
InChIKey: JRKZQRRYNCMSCB-UHFFFAOYAA
Std. InChI: InChI=1S/C10H11BrO/c11-5-3-8-1-2-10-9(7-8)4-6-12-10/h1-2,7H,3-6H2
Std. InChIKey: JRKZQRRYNCMSCB-UHFFFAOYSA-N
Product Categories of 5-(2-Bromoethyl)-2,3-dihydrobenzofuram (CAS NO.127264-14-6): Pharmaceutical material and intermeidates;Fluorobenzene;APIs Intermediate;INTERMEDIATESOFDARIFENACIN;Furan&Benzofuran;API intermediates;Aromatics Compounds;Furans;Aromatics;Heterocycles;Benzodiozoles, Benzodioxines & Benzodioxepines;Methyl Halides;Benzofuran

Safety Profile

 Hazard Codes: IrritantXi