1,5-Diazacyclooctane

1,5-Diazacyclooctane
Names
	Preferred IUPAC name 1,5-Diazocane
	Other names DACO, octahydro-1,5-diazocine
Identifiers
CAS Number	5687-07-0;
3D model (JSmol)	Interactive image;
ChemSpider	4416083;
PubChem CID	5248373;
CompTox Dashboard (EPA)	DTXSID701313786 ;
	InChI InChI=1S/C6H14N2/c1-3-7-5-2-6-8-4-1/h7-8H,1-6H2 Key: HTSQWLLKIZBMEO-UHFFFAOYSA-N;
	SMILES C1CNCCCNC1;
Properties
Chemical formula	C6H14N2
Molar mass	114.192 g·mol−1
Appearance	colorless liquid
Boiling point	78–80 °C (172–176 °F; 351–353 K) 16 Torr
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,5-Diazacyclooctane is an organic compound with the formula (CH₂CH₂CH₂NH)₂. It is a colorless oil. 1,5-Diazacyclooctane is a cyclic diamine.^[1]

Synthesis and reactions

It is prepared in low yield by the alkylation of ammonia with 1,3-dibromopropane.^[2]

The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with aldehydes to give bicyclic derivatives.^[3] When treated with transition metal salts, it serves as a chelating ligand.^[1]

Related compounds

References

^ ^a ^b Musker, W. Kenneth (1992). "Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles)". Coordination Chemistry Reviews. 117: 133–57. doi:10.1016/0010-8545(92)80022-J.
^ Daniel K. Mills; Ivan Font; Patrick J. Farmer; et al. (1998). "1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [ N,N′ -Bis(2-Mercaptoethyl)-1,5-Diazacyclooctanato]Nickel(II)". Inorganic Syntheses. Vol. 32. pp. 89–98. doi:10.1002/9780470132630.ch15. ISBN 9780471249214.
^ Billman, John H.; Dorman, Linneaus C. (1962). "Reaction of 1,5-Diazacyclooctane with Aldehydes". Journal of Organic Chemistry. 27 (7): 2419–22. doi:10.1021/jo01054a033.

[Musker-1] Musker, W. Kenneth (1992). "Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles)". Coordination Chemistry Reviews. 117: 133–57. doi:10.1016/0010-8545(92)80022-J.

[2] Daniel K. Mills; Ivan Font; Patrick J. Farmer; et al. (1998). "1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [ N,N′ -Bis(2-Mercaptoethyl)-1,5-Diazacyclooctanato]Nickel(II)". Inorganic Syntheses. Vol. 32. pp. 89–98. doi:10.1002/9780470132630.ch15. ISBN 9780471249214.

[3] Billman, John H.; Dorman, Linneaus C. (1962). "Reaction of 1,5-Diazacyclooctane with Aldehydes". Journal of Organic Chemistry. 27 (7): 2419–22. doi:10.1021/jo01054a033.

[1]

[2]

[3]