1,5-Diazacyclooctane

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1,5-Diazacyclooctane
1,5-DACO.png
Names
Preferred IUPAC name
1,5-Diazocane
Other names
DACO, octahydro-1,5-diazocine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H14N2/c1-3-7-5-2-6-8-4-1/h7-8H,1-6H2
    Key: HTSQWLLKIZBMEO-UHFFFAOYSA-N
  • C1CNCCCNC1
Properties
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).

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[edit]

It is prepared in low yield by the alkylation of hydrazine 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[edit]

References[edit]

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