3-FURANMETHANOL Chemical Properties

Boiling point:

79-80 °C17 mm Hg(lit.)

Density 

1.139 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.484(lit.)

Flash point:

101 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

14.49±0.10(Predicted)

form 

Liquid

color 

Clear colorless to slightly yellow

BRN 

106456

InChI

InChI=1S/C5H6O2/c6-3-5-1-2-7-4-5/h1-2,4,6H,3H2

InChIKey

STJIISDMSMJQQK-UHFFFAOYSA-N

SMILES

O1C=CC(CO)=C1

LogP

0.300

CAS DataBase Reference

4412-91-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36/37/39-36/37

RIDADR 

UN 1987 3/PG 3

WGK Germany 

3

HazardClass 

3.2

PackingGroup 

III

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich

3-FURANMETHANOL Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

3-Furanmethanol can be used in methods to support gastrointestinal homeostasis.

General Description

Furan-3-methanol on oxidation with pyridinium chlorochromate yields furan-3-carboxaldehyde.

Synthesis

General procedure for the synthesis of 3-furanmethanol from ethyl 3-furancarboxylate: To a solution of ethyl 3-furancarboxylate (7) (4.00 g, 28.5 mmol) in anhydrous ethyl ether (Et2O, 140 mL) was added lithium aluminum hydroxide (LiAlH4, 1.62 g, 42.8 mmol) batchwise at 0 °C. The reaction mixture was stirred at room temperature for 45 min. Subsequently, the reaction was quenched by sequential addition of water (H2O, 2 mL), 1 M sodium hydroxide (NaOH, 2 mL) and water (H2O, 6 mL) at 0 °C. The resulting white precipitate was removed by filtration and the solvent was removed by distillation under reduced pressure to give 3-furan methanol (8) (2.60 g, 93%) as a pale yellow oil. Thin layer chromatography (TLC) Rf value was 0.2 (unfolding agent: hexane/ethyl acetate, 4:1).1H NMR (CDCl3) δ: 7.42-7.41 (m, 1H, H2), 7.40-7.39 (m, 1H, H5), 6.44-6.42 (m, 1H, H4), 4.55 (s, 2H, CH2), 1.81 (br s. 1H, OH).13C NMR (CDCl3) δ: 143.3 (C5), 139.9 (C2), 125.1 (C3), 109.9 (C4), 56.1 (CH2). High Resolution Mass Spectrometry (HRMS-EI): m/z [M]+ calculated value for C5H6O2: 98.0368, measured value: 98.0371.

References

[1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2661 - 2679
[2] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 113 - 122
[3] Tetrahedron Letters, 1982, vol. 23, # 31, p. 3115 - 3118
[4] Tetrahedron Asymmetry, 2014, vol. 25, # 8, p. 677 - 689
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617

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