Aminocyclopropane

Last updated
Aminocyclopropane
C3H5NH2.svg
Names
Other names
cyclopropylamine, CPA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.038 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-142-2
KEGG
PubChem CID
UNII
  • InChI=1S/C3H7N/c4-3-1-2-3/h3H,1-2,4H2
    Key: HTJDQJBWANPRPF-UHFFFAOYSA-N
  • C1CC1N
Properties
C3H7N
Molar mass 57.096 g·mol−1
Appearancecolorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Warning
H225, H302, H314, H317, H332, H412
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).

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]

Cyclopropylamines can be prepared by the Kulinkovich reaction, by dialkylation of bromonitromethane, and various cyclopropanations. [3] [4]

References

  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.
  2. 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.
  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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