3-IODO-TETRAHYDRO-FURAN Chemical Properties

Boiling point:

187.0±33.0 °C(Predicted)

Density 

1.93±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

liquid

color 

Dark brown

InChI

InChI=1S/C4H7IO/c5-4-1-2-6-3-4/h4H,1-3H2

InChIKey

BKIQORJIKOPRCG-UHFFFAOYSA-N

SMILES

O1CCC(I)C1

Safety Information

HS Code 

2932190090

3-IODO-TETRAHYDRO-FURAN Usage And Synthesis

Physical Form

liquid

Uses

3-Iodotetrahydrofuran is used to study transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water.

Synthesis

3-Hydroxytetrahydrofuran (8.8 g, 0.1 mol) was used as starting material and dissolved in dichloromethane (200 mL). Triphenylphosphine (52.4 g, 0.2 mol), imidazole (13.6 g, 0.2 mol) and iodine (50.7 g, 0.2 mol) were added sequentially to this solution. The reaction mixture was heated to reflux overnight under nitrogen protection. Upon completion of the reaction, 0.2 M sodium thiosulfate solution (30 mL) was added to quench the reaction. The organic layer was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to give a wet yellow solid. The solid was dissolved in pentane (100 mL) and stirred for 2 h. The insoluble material was removed by filtration and the filtrate was concentrated to give the final 3-iodotetrahydrofuran (18.6 g, 94% yield).

References

[1] Patent: CN103965174, 2016, B. Location in patent: Paragraph 0171; 0173-0175
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 22, p. 6170 - 6174
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 3, p. 933 - 937
[4] Angew. Chem., 2012, vol. 125, # 3, p. 967 - 971,5

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