6,7-Dihydro-4(5H)-benzofuranone Chemical Properties

Melting point:

30-34 °C (lit.)

Boiling point:

115-118 °C/16 mmHg (lit.)

Density 

1.162 g/mL at 25 °C (lit.)

refractive index 

1.53-1.532

Flash point:

>230 °F

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

Liquid

Specific Gravity

1.162

color 

Clear yellow to brown

InChI

InChI=1S/C8H8O2/c9-7-2-1-3-8-6(7)4-5-10-8/h4-5H,1-3H2

InChIKey

DXWQOYPYNPSVRL-UHFFFAOYSA-N

SMILES

O1C2CCCC(=O)C=2C=C1

CAS DataBase Reference

16806-93-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29143900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

6,7-Dihydro-4(5H)-benzofuranone Usage And Synthesis

Chemical Properties

clear yellow to brown low melting solid or liquid

Uses

6,7-Dihydro-4(5H)-benzofuranone may be used in the synthesis of furacridone ring skeleton.

Definition

ChEBI: 6,7-Dihydro-4(5H)-benzofuranone is a member of benzofurans.

Synthesis Reference(s)

Tetrahedron, 51, p. 3087, 1995 DOI: 10.1016/0040-4020(95)00070-O
Tetrahedron Letters, 27, p. 1127, 1986 DOI: 10.1016/S0040-4039(00)84195-7

General Description

6,7-Dihydro-4(5H)-benzofuranone is a benzofuran derivative that consists of fused benzene and furan ring. Its standard molar enthalpy of formation by static bomb calorimetry and standard molar enthalpy of vaporization using Calvet microcalorimetry has been measured. These values have been used to derive the standard molar enthalpy of formation in gaseous phase.

Synthesis

Under argon protection, 1,3-cyclohexanedione (20.71 g, 0.18 mol) was dissolved in methanol (100 mL) and the solution was cooled to 0 °C. Subsequently, potassium hydroxide (12.2 g, 0.18 mol) was added to the solution and stirred continuously for 30 minutes at 0 °C. Next, 50% aqueous chloroacetaldehyde solution (26.3 mL, 0.203 mol) was slowly added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solution was acidified to pH < 7 with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline, and dried over anhydrous magnesium sulfate. Finally, the solvent was removed by concentration under reduced pressure to give the crude 6,7-dihydro-4(5H)-benzofuranone product (16.5 g), which was pure enough to be used directly in the next step of the reaction.

References

[1] Arkivoc, 2011, vol. 2011, # 9, p. 1 - 14
[2] Heterocycles, 2004, vol. 62, p. 807 - 813
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1966 - 1982
[4] Journal of Organic Chemistry, 1988, vol. 53, # 17, p. 4135 - 4137
[5] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 10, p. 2167 - 2169

6,7-Dihydro-4(5H)-benzofuranone(16806-93-2)Related Product Information

• 2,3-Dihydrobenzofuran
• Benzofuran
• 5-Bromo-1-benzofuran
• Tetrahydrofuran
• Furazolidone
• Dibenzofuran
• POLY(TETRAHYDROFURAN) STANDARD 15000
• 4-OXO-4,5,6,7-TETRAHYDROBENZO[B]FURAN-3-CARBOXYLIC ACID
• 6,6-DIMETHYL-6,7-DIHYDRO-1-BENZOFURAN-4(5H)-ONE
• 3-ACETYL-2,6,6-TRIMETHYL-5,6,7-TRIHYDROOXAINDEN-4-ONE
• 6,6-DIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-1-BENZOFURAN-3-CARBOXYLIC ACID
• (2,6,6-TRIMETHYL-4-OXO-4,5,6,7-TETRAHYDRO-BENZOFURAN-3-YL)-ACETIC ACID
• 6,7-Dihydro-4(5H)-benzofuranone
• TOSLAB 775839
• 3-METHYL-4-OXO-4,5,6,7-TETRAHYDRO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER
• 4-BROMO-N-(4-CHLORO-9-OXO-6,7,8,9-TETRAHYDRODIBENZO[B,D]FURAN-2-YL)BENZENESULFONAMIDE
• TOSLAB 797821
• 2-METHYL-N-(9-OXO-6,7,8,9-TETRAHYDRODIBENZO[B,D]FURAN-2-YL)BENZENESULFONAMIDE