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IUPAC name Cyclopropane
CAS number 75-19-4
Molecular formula C3H6
Molar mass 42.08 g/mol
Density 1.879 g/L (1 atm, 0 °C)
Melting point

-128 °C

Boiling point

-33 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. The bonds between the carbon atoms are a great deal weaker than in a typical carbon-carbon bond. This is the result of the 60° angle between the carbon atoms, which is far less than the normal angle of 109.5°. For bonds between atoms with sp3 hybridised orbitals. This angle strain has to be subtracted from the normal C-C bond energy, making the resultant compound more reactive than acyclic alkanes and other cycloalkanes such as cyclohexane and cyclopentane. This is the banana bond description of cycloalkanes.

There is also torsional strain because the hydrogen atoms are held in the eclipsed conformation.

However, cyclopropanes are more stable than a simple angle strain analysis would suggest. Cyclopropane can also be modeled as a three-center-bonded orbital combination of methylene carbenes. This results in the Walsh orbital description of cyclopropane, where the C-C bonds have mostly pi character. This is also why cyclopropanes often have reactivity similar to alkenes. This is also why carbenes can easily add into alkenes to produce cyclopropanes. Cyclopropanes taken to the extreme are tetrahedranes and propellanes.

Cyclopropane is an anaesthetic when inhaled, but has been superseded by other agents in modern anaesthetic practice. This is due to its extreme reactivity under normal conditions: when the gas is mixed with oxygen there is a significant risk of explosion.



Because of the strain in the carbon-carbon bonds of cyclopropane, the molecule has an enormous amount of potential energy. In pure form, it will break down to form linear hydrocarbons, including "normal", non-cyclic propene. This decomposition is potentially explosive, especially if the cyclopropane is liquified, pressurized, or contained within tanks. Explosions of cyclopropane and oxygen are even more powerful, because the energy released by the formation of normal propane is compounded by the energy released via the oxidation of the carbon and hydrogen present. At room temperature, sufficient volumes of liquified cyclopropane will self-detonate. To guard against this, the liquid is shipped in cylinders filled with tungsten wool, which prevents high-speed collisions between molecules and vastly improves stability. Pipes to carry cyclopropane must likewise be of small diameter, or else filled with unreactive metal or glass wool, to prevent explosions. Even if these precautions are followed, cyclopropane is dangerous to handle and manufacture, and is no longer used for anaesthesia.


Cyclopropanes are a class of organic compounds sharing the common cyclopropane ring, in which one or more hydrogens may be substituted. These compounds are found in biomolecules; for instance, the pyrethrum insecticides (found in certain Chrysanthemum species) contain a cyclopropane ring.

Organic synthesis

Cyclopropanes can be prepared in the laboratory by organic synthesis in various ways and many methods are simply called cyclopropanation:

a possible reaction mechanism for this cyclopropanation was proposed[5]:
  • an intramolecular Wurtz coupling for example in the synthesis of bicyclo[1.1.0]butane[11]
  • Rearrangement reaction of certain cyclobutane compounds for instance the conversion of 1,2-cyclobutanediol to cyclopropanecarboxaldehyde[12]
  • photochemical rearrangement reaction of 1,4-dienes to vinylcyclopropanes in the di-pi-methane rearrangement[13]

Organic reactions

Although cyclopropanes are formally cycloalkanes, they are very reactive due to considerable strain energy and due to double bond character.

  • Cyclopropyl groups participate in cycloaddition reaction such as the formal [5+2]cycloaddition shown below:
This asymmetric synthesis is catalyzed by a rhodium BINAP system with 96% enantiomeric excess[14].
This reaction is catalyzed by platinum(II) chloride in a carbon monoxide environment. The proposed reaction mechanism is supported by deuterium labeling[16].
In another version of the same reaction[17] the catalyst is PdBr2 is prepared in situ from palladium(II) acetate and copper(II) bromide and the solvent is toluene.


  1. ^ Merck Index, 11th Edition, 2755.
  2. ^
  3. ^ Cyclopropanemethanol, 2-phenyl-, (1S-trans)- André B. Charette and Hélène Lebel Organic Syntheses, Coll. Vol. 10, p.613 (2004); Vol. 76, p.86 (1999) Link
  4. ^ Unusual Ambiphilic Carbenoid Equivalent in Amide Cyclopropanation Kuo-Wei Lin, Shiuan Yan, I-Lin Hsieh, and Tu-Hsin Yan Org. Lett.; 2006; 8(11) pp 2265 - 2267; Abstract
  5. ^ Reaction mechanism: Magnesium reacts with titanium tetrachloride 1 to Grignard reagent 2 in equilibrium with divalent Titanium(II) chloride 3 which adds to dichloromethane to adduct 4. Another insertion of magnesium and loss of magnesium dichloride gives the Schrock carbene 6 which reacts with the carbonyl group in amide 7. Loss of titanium oxychloride gives the enamine 9 which continuous to react with another carbene and finally to the cyclopropane. Notes: Instead of chloride, titanium can also be coordinated to solvent. In equally plausible mechanisms the intermediates are Simmons-Smith like
  6. ^ [1.1.1]propellane Kathleen R. Mondanaro and William P. Dailey Organic Syntheses, Coll. Vol. 10, p.658 (2004); Vol. 75, p.98 (1998) Link
  7. ^ Butanoic acid, 3,3-dimethyl-4-oxo-, methyl ester Hans-Ulrich Reissig, Ingrid Reichelt, and Thomas Kunz Organic Syntheses, Coll. Vol. 9, p.573 (1998); Vol. 71, p.189 (1993). Link
  8. ^ Cyclopropylaetylene Edward G. Corley, Andrew S. Thompson, Martha Huntington Organic Syntheses, Coll. Vol. 10, p.456 (2004); Vol. 77, p.231 (2000) Link.
  9. ^ A new asymmetric organocatalytic nitrocyclopropanation reaction Henriette M. Hansen, Deborah A. Longbottom and Steven V. Ley Chem. Commun., 2006, 4838 - 4840, doi:10.1039/b612436b
  10. ^ The initial reaction is a Michael addition. Solvent dichloromethane, 64% enantiomeric excess
  11. ^ Bicyclo[1.1.0]butane Gary M. Lampman and James C. Aumiller Organic Syntheses, Coll. Vol. 6, p.133 (1988); Vol. 51, p.55 (1971) Link.
  12. ^ J. P. Barnier, J. Champion, and J. M. Conia Organic Syntheses, Coll. Vol. 7, p.129 (1990); Vol. 60, p.25 (1981) Link.
  13. ^ IUPAC Gold book definition
  14. ^ Asymmetric Catalysis of the [5 + 2] Cycloaddition Reaction of Vinylcyclopropanes and -Systems Paul A. Wender, Lars O. Haustedt, Jaehong Lim, Jennifer A. Love, Travis J. Williams, and Joo-Yong Yoon J. Am. Chem. Soc.; 2006; 128(19) pp 6302 - 6303; Abstract
  15. ^ PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes Alois Fürstner and Christophe Aïssa J. Am. Chem. Soc.; 2006; 128(19) pp 6306 -6307; Abstract
  16. ^ Reaction mechanism: The starting compound contains one deuterium atom (D), in the first step PtCl2 coordinates to the double bond in 1a. The next step is oxidative addition to 1b which is a non-classical ion. This intermediate rearranges to the cyclobutane carbocation 1c which has also some carbene character through one of its resonance structures. The next step is a deuterium migration to the more stable benzylic carbocation after which the cyclobutene is liberated.
  17. ^ Palladium-Catalyzed Ring Enlargement of Aryl-Substituted Methylenecyclopropanes to Cyclobutenes Min Shi, Le-Ping Liu, and Jie Tang J. Am. Chem. Soc.; 2006; 128(23) pp 7430 - 7431; doi:10.1021/ja061749y
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cyclopropane". A list of authors is available in Wikipedia.
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