Chemical Properties
Clear and colourless, volatile liquid
Uses
FLAMMABLE LIQUID, CORROSIVE
Application
Cyclopropylamine is mainly used in organic synthesis, pharmaceutical synthesis intermediates, and can be used in the synthesis of new antibacterial drugs ciprofloxacin products, such as the synthesis of ciprofloxacin, enrofloxacin, spafloxacin and other drugs. In addition, cyclopropylamine is also an important intermediate for the synthesis of pesticides, plant protection agents and herbicides, such as 2-chloro-4-6-cyclopropyl-s-triazine, cyprochlor, cyproterazine, cyprocyanine and other cyclopropanes class of pesticides.
Definition
ChEBI: A primary aliphatic amine that consists of cyclopropane bearing a single amino substituent.
Preparation
Cyclopropylamine is synthesized from 1,3-propanediol by bromination, cyanation, cyclization, amidation, and Hoffmann rearrangement. It is also synthesized with γ-butyrolactone and isopropanol by five steps of ring-opening esterification, cyclization, hydrolysis, acylation and Hofmann degradation.
Biochem/physiol Actions
Cyclopropylamine inactivates cytochrome P450 enzymes by a mechanism involving initial one-electron oxidation at nitrogen followed by scission of the cyclopropane ring leading to covalent modification of the enzyme. It is a mechanism-based inhibitor of quinoprotein methylamine dehydrogenase from Paracoccus denitrificans.
Purification Methods
It has been isolated as the benzamide m 100.6-101.0o (from aqueous EtOH). It forms a picrate m 149o (from EtOH/pet ether) from which the free base can be recovered using a basic ion-exchange resin and can then be distilled through a Todd column (p 11) using an automatic still head which only collects products boiling below 51o/atm. Polymeric materials if present will boil above this temperature. The hydrochloride has m 85-86o [Roberts & Chambers J Am Chem Soc 73 5030 1951, Jones J Org Chem 9 484 1944, Emmons J Am Chem Soc 79 6522 1957]. [Beilstein 12 IV 3.]
