Cyclopropylamine

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] Cycloproylamine is first member of the aminocycloalkanes, which includes cyclobutylamine, cyclopentylamine, and cyclohexylamine.

Cyclopropylamine

Names
Other names aminocyclopropane, CPA
Identifiers
CAS Number	765-30-0 Y
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:
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

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]