Cyclopropylamine
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| Names | |
|---|---|
| Other names
aminocyclopropane, CPA | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | CPA |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.011.038 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C3H7N | |
| Molar mass | 57.096 g·mol−1 |
| Appearance | colorless liquid |
| Melting point | −35.4 °C (−31.7 °F; 237.8 K) |
| Boiling point | 49–50 °C (120–122 °F; 322–323 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H225, H302, H314, H317, H332, H412 | |
| P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P362+P364, P363, P370+P378, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclopropylamine is the organic compound with the formula C3H5NH2. It is a simple amine derivative of cyclopropane.[1] As a precursor to pesticides and pharmaceuticals, it is produced on a multi-ton scale from the carboxamide.[2] Cyclopropylamine is first member of the aminocycloalkanes, which includes cyclobutylamine, cyclopentylamine, and cyclohexylamine.
Cyclopropylamines
[edit]Many aminocyclopropanes are known, most prominently the amino acid aminocyclopropane-1-carboxylic acid.
The cyclopropylamine group is featured in several pharmaceutical drugs:[2]
- Simeprevir, used to treat hepatitis C infections
- Risdiplam, used to treat spinal muscular atrophy
- ciprofloxacin, an antibiotic.
Cyclopropylamines can be prepared by the Kulinkovich reaction, by dialkylation of bromonitromethane, and various cyclopropanations.[3][4]
References
[edit]- ↑ Bertus, Philippe; Caillé, Julien (2025). "Advances in the Synthesis of Cyclopropylamines". Chemical Reviews. 125 (6): 3242–3377. doi:10.1021/acs.chemrev.4c00674. PMID 40048498.
- 1 2 Huang, Jinpei; Geng, Yuhao; Wang, Yundong; Xu, Jianhong (2019). "Efficient Production of Cyclopropylamine by a Continuous-Flow Microreaction System". Industrial & Engineering Chemistry Research. 58 (36): 16389–16394. doi:10.1021/acs.iecr.9b02438.
- ↑ Cha, Jin Kun; Kulinkovich, Oleg G. (2012). "The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives". Organic Reactions. pp. 1–160. doi:10.1002/0471264180.or077.01. ISBN 978-0-471-26418-7.
- ↑ Sokolova, Olga O.; Bower, John F. (2021). "Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives" (PDF). Chemical Reviews. 121 (1): 80–109. doi:10.1021/acs.chemrev.0c00166. PMID 32567848 – via University of Liverpool Repository.