{{Chembox | ImageFile = C3H5NH2.svg | ImageSize = 130px | ImageAlt = | IUPACName = | OtherNames = aminocyclopropane, CPA |Section1={{Chembox Identifiers | CASNo = 765-30-0 | CASNo_Ref = {{Cascite|correct|CAS}} | ChEBI = 34660 | ChemSpiderID = 63025 | EC_number = 212-142-2 | KEGG = C14150 | PubChem = 69828 | UNII = 8PR8XTH1X1 | StdInChI=1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2 | StdInChIKey = HTJDQJBWANPRPF-UHFFFAOYSA-N | SMILES = C1CC1N }} |Section2={{Chembox Properties | C = 3|H=7|N=1 | MolarMass = | RefractIndex = | Appearance = colorless liquid | Density = | MeltingPtC = -35.4 | MeltingPt_notes = | BoilingPtC = 49-50 | BoilingPt_notes = | Solubility = }} |Section3={{Chembox Hazards | GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/69828#section=Safety-and-Hazards] | GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|225|302|314|317|332|412}} | PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|264+265|270|271|272|273|280|301+317|301+330+331|302+352|302+361+354|303+361+353|304+340|305+354+338|316|317|321|330|333+317|362+364|363|370+378|403+235|405|501}} | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Cyclopropylamine''' is the organic compound with the formula {{chem2|C3H5NH2}}. It is a simple amine derivative of cyclopropane.<ref>{{cite journal|doi=10.1021/acs.chemrev.4c00674 |title=Advances in the Synthesis of Cyclopropylamines |date=2025 |last1=Bertus |first1=Philippe |last2=Caillé |first2=Julien |journal=Chemical Reviews |volume=125 |issue=6 |pages=3242–3377 |pmid=40048498 }}</ref> As a precursor to pesticides and pharmaceuticals, it is produced on a multi-ton scale from the carboxamide.<ref name=Eff>{{cite journal |doi=10.1021/acs.iecr.9b02438 |title=Efficient Production of Cyclopropylamine by a Continuous-Flow Microreaction System |date=2019 |last1=Huang |first1=Jinpei |last2=Geng |first2=Yuhao |last3=Wang |first3=Yundong |last4=Xu |first4=Jianhong |journal=Industrial & Engineering Chemistry Research |volume=58 |issue=36 |pages=16389–16394 }}</ref> Cyclopropylamine is first member of the aminocycloalkanes, which includes cyclobutylamine, cyclopentylamine, and cyclohexylamine.
==Cyclopropylamines== Many aminocyclopropanes are known, most prominently the amino acid aminocyclopropane-1-carboxylic acid.
The cyclopropylamine group is featured in several pharmaceutical drugs:<ref name=Eff/> *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.<ref>{{cite book |doi=10.1002/0471264180.or077.01 |chapter=The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives |title=Organic Reactions |date=2012 |last1=Cha |first1=Jin Kun |last2=Kulinkovich |first2=Oleg G. |pages=1–160 |isbn=978-0-471-26418-7 }}</ref><ref>{{cite journal |last1=Sokolova |first1=Olga O. |last2=Bower |first2=John F. |date=2021 |title=Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives |url=https://livrepository.liverpool.ac.uk/3117450/1/Cyclopropylamine%20Chem%20Rev%20Revised%20version%204%20no%20highlights.pdf |journal=Chemical Reviews |volume=121 |issue=1 |pages=80–109 |doi=10.1021/acs.chemrev.0c00166 |pmid=32567848 |via=University of Liverpool Repository}}</ref>
==References== <references />
Category:Amines Category:Cyclopropyl compounds