Aminocyclopropane

Aminocyclopropane
Names
	Other names cyclopropylamine, CPA
Identifiers
CAS Number	765-30-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34660;
ChemSpider	63025;
ECHA InfoCard	100.011.038
EC Number	212-142-2;
KEGG	C14150;
PubChem CID	69828;
UNII	8PR8XTH1X1;
CompTox Dashboard (EPA)	DTXSID9061099 ;
	InChI InChI=1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2 Key: HTJDQJBWANPRPF-UHFFFAOYSA-N;
	SMILES C1CC1N;
Properties
Chemical formula	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:[1]
Pictograms
Signal word	Warning
Hazard statements	H225, H302, H314, H317, H332, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, 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). Infobox references

Aminocyclopropane 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]

Cyclopropylamines

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

^ 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.
^ ^a ^b 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". Chemical Reviews. 121 (1): 80–109. doi:10.1021/acs.chemrev.0c00166. PMID 32567848.

[1] 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.

[Eff-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.

[3] 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.

[4] Sokolova, Olga O.; Bower, John F. (2021). "Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives". Chemical Reviews. 121 (1): 80–109. doi:10.1021/acs.chemrev.0c00166. PMID 32567848.

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