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1,5-Diazacyclooctane
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1,5-DACO.png 133 1,5-Diazocane DACO, octahydro-1,5-diazocine 5687-07-0 correct FDA ZQ8KR7BLU5 5248373 4416083 1S/C6H14N2/c1-3-7-5-2-6-8-4-1/h7-8H,1-6H2 HTSQWLLKIZBMEO-UHFFFAOYSA-N C1CNCCCNC1
6 14 2 colorless liquid 78-80 16 Torr
1,5-Diazacyclooctane is an organic compound with the formula (CH2CH2CH2NH)2. It is a colorless oil. 1,5-Diazacyclooctane is a cyclic diamine.Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles) Musker, W. Kenneth Coordination Chemistry Reviews 1992 117 133–57 10.1016/0010-8545(92)80022-J
Synthesis and reactions
It is prepared in low yield by the alkylation of ammonia with 1,3-dibromopropane.Inorganic Syntheses Daniel K. Mills Ivan Font Patrick J. Farmer Yui-May Hsiao Thawatchai Tuntulani Rizalia M. Buonomo Dawn C. Goodman Ghezai Musie Craig A. Grapperhaus Michael J. Maguire Chia-Huei Lai Michelle L. Hatley Jason J. Smee John A. Bellefeuille Marcetta Y. Darensbourg 1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [ N,N′ -Bis(2-Mercaptoethyl)-1,5-Diazacyclooctanato]Nickel(II) 3 1998 32 89–98 10.1002/9780470132630.ch15 9780471249214
The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with aldehydes to give bicyclic derivatives.Reaction of 1,5-Diazacyclooctane with Aldehydes Billman, John H. Dorman, Linneaus C. Journal of Organic Chemistry 1962 27 7 2419–22 10.1021/jo01054a033 When treated with transition metal salts, it serves as a chelating ligand.
Related compounds
1,4-Diazacycloheptane
1,5-Diaza-3,7-diphosphacyclooctanes
Tröger's base
References
Category:Diamines
Category:Chelating agents
Category:Nitrogen heterocycles
Category:Diazocines