Cyclobutylamine

Cyclobutylamine
Names
	Other names aminocyclobutane
Identifiers
CAS Number	2516-34-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	68166;
ECHA InfoCard	100.017.942
EC Number	219-736-0;
PubChem CID	75645;
UNII	HFH6FE5D4Y;
CompTox Dashboard (EPA)	DTXSID00870982 ;
	InChI InChI=1S/C4H9N/c5-4-2-1-3-4/h4H,1-3,5H2 Key: KZZKOVLJUKWSKX-UHFFFAOYSA-N;
	SMILES C1CC(C1)N;
Properties
Chemical formula	C4H9N
Molar mass	71.123 g·mol−1
Appearance	colorless liquid
Boiling point	80.5–81.5 °C (176.9–178.7 °F; 353.6–354.6 K)
Refractive index (nD)	1.4356
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, 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

Cyclobutylamine is an organic compound with the formula C₄H₇NH₂. It is a colorless, readily distillable liquid. It can be prepared from cyclobutanecarboxylic acid via the amide or by Curtius rearrangement.^[1] Cyclobutylamine is a member of the aminocycloalkanes, which also includes cyclopropylamine, cyclopentylamine, and cyclohexylamine.

Oxidation with potassium permanganate gives cyclobutanone.^[2]

Using "strain-relief reaction", substituted bicyclobutanes can be converted to a variety of N-substituted cyclobutylamines.^[3]

References

^ Newton W. Werner, Joseph Casanova, Jr. (1967). "Cyclobutylamine". Organic Syntheses. 47: 28. doi:10.15227/orgsyn.047.0028.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Lee, Donald G.; Ribagorda, María; Adrio, Javier (2007). "Potassium Permanganate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rp244.pub2. ISBN 978-0-471-93623-7.
^ Gianatassio, Ryan; Lopchuk, Justin M.; Wang, Jie; Pan, Chung-Mao; Malins, Lara R.; Prieto, Liher; Brandt, Thomas A.; Collins, Michael R.; Gallego, Gary M.; Sach, Neal W.; Spangler, Jillian E.; Zhu, Huichin; Zhu, Jinjiang; Baran, Phil S. (2016). "Strain-release amination". Science. 351 (6270): 241–246. Bibcode:2016Sci...351..241G. doi:10.1126/science.aad6252. PMC 4730898. PMID 26816372.

[1] Newton W. Werner, Joseph Casanova, Jr. (1967). "Cyclobutylamine". Organic Syntheses. 47: 28. doi:10.15227/orgsyn.047.0028.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[2] Lee, Donald G.; Ribagorda, María; Adrio, Javier (2007). "Potassium Permanganate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rp244.pub2. ISBN 978-0-471-93623-7.

[3] Gianatassio, Ryan; Lopchuk, Justin M.; Wang, Jie; Pan, Chung-Mao; Malins, Lara R.; Prieto, Liher; Brandt, Thomas A.; Collins, Michael R.; Gallego, Gary M.; Sach, Neal W.; Spangler, Jillian E.; Zhu, Huichin; Zhu, Jinjiang; Baran, Phil S. (2016). "Strain-release amination". Science. 351 (6270): 241–246. Bibcode:2016Sci...351..241G. doi:10.1126/science.aad6252. PMC 4730898. PMID 26816372.

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