| Identification | Back Directory | [Name]
cyclopropanol | [CAS]
16545-68-9 | [Synonyms]
opropanoL
cyclopropanol
2-Cyclopropanol
Cyclopropane-1-ol
(1α)-Cyclopropanol
cyclopropyl alcohol
Hydroxycyclopropane
16545-68-9, CFCD16545689 | [Molecular Formula]
C3H6O | [MDL Number]
MFCD19707103 | [MOL File]
16545-68-9.mol | [Molecular Weight]
58.08 |
| Chemical Properties | Back Directory | [Melting point ]
180℃ | [Boiling point ]
101-102℃ (760 Torr) | [density ]
9.9110 g/cm3 | [refractive index ]
1.4129 (589.3 nm 20℃) | [storage temp. ]
Sealed in dry,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 |
| Hazard Information | Back Directory | [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. |
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