cyclopropanol Chemical Properties

Melting point:

180℃

Boiling point:

101-102℃ (760 Torr)

Density 

9.9110 g/cm3

refractive index 

1.4129 (589.3 nm 20℃)

storage temp. 

2-8°C

pka

15.31±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C3H6O/c4-3-1-2-3/h3-4H,1-2H2

InChIKey

YOXHCYXIAVIFCZ-UHFFFAOYSA-N

SMILES

C1(O)CC1

Safety Information

RIDADR 

UN1993

HazardClass 

3

cyclopropanol Usage And Synthesis

Description

Cyclopropanols can be readily synthesized via synthetic transformations such as the Kulinkovich cyclopropanation and the Simmons-Smith reaction [1]. Due to the high strains built intrinsically in the three-membered ring, cyclopropanols and their derivatives are highly reactive and can undergo various ring opening/expansion/fragmentation reactions. A significant amount of these ring opening/expansion/fragmentation reactions are catalyzed/promoted by transition metal complexes. In many of these cases, cyclopropanols and their derivatives are considered as the equivalents of homoenolates or β-alkyl radicals.

Uses

Cyclopropanol is a basic building block.

Definition

ChEBI: Cyclopropanol is a cyclopropane in which a hydrogen atom is replaced by a hydroxy group. It is a member of cyclopropanes and an aliphatic alcohol.

Synthesis

Step 1: Synthesis of cyclopropyl-1-ol Cyclopropylboronic acid (10 g, 0.116 mol) and aqueous sodium hydroxide (8.37 g, 0.209 mol, dissolved in 100 mL of water) were added to a 1 L reaction flask. Under the cooling of an ice bath, 34% hydrogen peroxide (80 mL) was slowly added dropwise, keeping the reaction temperature not higher than 5 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 5°C for 1 hour. Upon completion of the reaction, saturated aqueous sodium thiosulfate solution was added slowly and dropwise to quench the reaction until the potassium iodide-starch test paper no longer showed color. The reaction solution was extracted with ether three times, the organic phases were combined, washed with saturated brine, dried with anhydrous desiccant, filtered and concentrated under reduced pressure at 0 °C to give cyclopropan-1-ol (colorless oil, 4 g, 60% yield). The product did not need further purification and could be used directly in the subsequent reaction. (MS detection: [M+1] not observed)

References

[1] Xinpei Cai, Mingji Dai, Weida Liang. “Total syntheses via cyclopropanols.” Tetrahedron 75 2 (2019): Pages 193-208.

cyclopropanol(16545-68-9)Related Product Information

• Furfuryl alcohol
• PROFLURALIN