2,3-Dihydrobenzofuran Chemical Properties

Melting point:

-21°C

Boiling point:

188-189 °C (lit.)

Density 

1.065 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.549(lit.)

Flash point:

152 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

alcohol: soluble

form 

clear liquid

Specific Gravity

1.065

color 

Colorless to Yellow to Green

Merck 

14,2559

BRN 

111928

InChI

1S/C8H8O/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2

InChIKey

HBEDSQVIWPRPAY-UHFFFAOYSA-N

SMILES

C1Cc2ccccc2O1

LogP

2.140

CAS DataBase Reference

496-16-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzofuran, 2,3-dihydro-(496-16-2)

EPA Substance Registry System

Coumaran (496-16-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-26

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

TSCA listed

HS Code 

29329995

Storage Class

10 - Combustible liquids

MSDS

• Language:English Provider:Coumaran
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,3-Dihydrobenzofuran Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

2,3-dihydrobenzofuran is widely used in the synthesis of tricyclic compounds and is also an intermediate raw material for the synthesis of some important drugs. It is used in the synthesis of antitumor agents benzofuran sulfonylureas, HIV protease inhibitor amino acid hydroxyethylenesulfonyl, matrix metalloproteinase inhibitor aryl sulfinyl isoxime hydroxamic acid, etc.

Definition

ChEBI: 2,3-dihydrobenzofuran is a member of the class of 1-benzofurans that is the 2,3-dihydroderivative of benzofuran. It has a role as a metabolite.

General Description

Biotransformation of 2,3-dihydrobenzofuran using intact cells of Pseudomonas putida UV4 has been investigated. 2,3-Dihydrobenzofuran is the intermediate formed during catalytic hydrodeoxygenation of benzofuran.

Synthesis

Step 1: Synthesis of 2-phenoxyethanol
Add 200 ml of anhydrous ethanol to a 10000 m L three-necked round-bottomed flask, dissolve sodium metal (23 g) in it, then add phenol (94 g, 900 mL), 2-chloroethanol (700 mL) , respectively, and heat and reflux until the reaction mixture is neutral. The reaction was tracked by running a plate during the reaction (unfolding agent: chloroform:methanol:benzene=200:1:1 ; Rf=0.3). Ethanol was removed by distillation under reduced pressure with a rotary evaporator, and 500 mL of distilled water was added. It was then extracted with ether three times (about 400 mL each time) and washed several times with dilute sodium hydroxide solution and distilled water respectively (to remove phenol). The ether was then removed by distillation at atmospheric pressure, and the residue was distilled under reduced pressure to collect a fraction of 163-166°C (18 mmHg) was obtained. The ether is a colorless thick liquid, bp : 240-246°C, refractive index: 1.532, d:1.1002, insoluble in water but soluble in ether and alcohol (yield: 75 %).
Step 2: Synthesis of 2,3-dihydrobenzofuran
To a 250 mL three-necked round-bottomed flask, 2-phenoxyethanol (50 g) and zinc chloride (5 g) were added and heated to 225°C reflux with mixing and stirring, then slowly reduced to 190C reflux. The reaction was carried out over 5h with a running plate to follow the reaction (unfolding agent:chloroform:methanol:benzene=20:1:1 ; Rf=0.6). Cooling, distillation under reduced pressure and collection of (88-90)°C ( 18 mmHg) fraction gave the title compound. The compound was a colorless liquid, b p : 188-189??C, refractive index: 1.549, d 1.053 , yield: (70%).

2,3-Dihydrobenzofuran(496-16-2)Related Product Information

• 2H-Indeno[5,4-b]furan-8-ethanamine, 1,6,7,8-tetrahydro-, (8R)-
• Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)propenoate
• WBYZCPYZHMZPHD-UHFFFAOYSA-N
• 4-bromo-1,2,6,7-tetrahydro-8H-Indeno[5,4-b]furan-8-one
• 3-(2,3-DIHYDRO-BENZOFURAN-5-YL)-PROPIONIC ACID ETHYL ESTER
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• Potassium hydrogen phthalate
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• STERIGMATOCYSTIN
• 2,3-Dihydrobenzofuran-3-one
• THEBAINE
• AFLATOXIN G1
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• NALORPHINE HYDROCHLORIDE
• MARITIMEIN
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• (-)-USNIC ACID