Azepan

Structural formula
General
Surname	Azepan
other names	Hexamethyleneimine; Hexahydroazepine; Azacycloheptane; Homopiperidine;
Molecular formula	C 6 H 13 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
EC number	203-875-9
ECHA InfoCard	100.003.524
PubChem	8119
Wikidata	Q421530
properties
Molar mass	99.18 g mol −1
Physical state	liquid
density	0.86 g cm −3
Melting point	−37 ° C
boiling point	135-138 ° C
Vapor pressure	12.5 h Pa (20 ° C)
solubility	miscible with water
Refractive index	1.4631 (20 ° C)
safety instructions
H and P phrases	H: 225-302-331-314
	P: 210-280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
Toxicological data	20.7 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Azepan is a saturated heterocyclic chemical compound . It is the simplest seven - membered nitrogen- containing heterocycle and is also often referred to as hexamethyleneimine . However, this designation is a bit misleading, because it is not an imine in the (today's) actual sense. Another name is homopiperidine , as it is a homologue of piperidine that is extended by a methylene group .

Manufacturing

The synthesis of Azepan can be prepared by reduction of ε-caprolactam with lithium aluminum hydride or sodium borohydride be performed. The cyclization of 1,6-diaminohexane, for example on a ruthenium catalyst (in this case tris (triphenylphosphino) dichlororuthenate (II) ) is a synthetic route.

properties

Azepan is a colorless liquid with an ammonia- like odor. It is completely miscible with water. It is a nitrogen base . Their pKa value in water is 11.4 at 20 ° C.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on hexamethyleneimine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-280.
↑ L. Ruzicka, M. Kobelt, O. Hafliger, V. Prelog in: Helvetica Chimica Acta 1949, 32, 544–552.
^ SR Wann, PT Thorsen, MM Kreevoy in: J. Org. Chem. 1981, 46, 12, 2579-2581.
↑ Bui-The-Khai, C. Concilio, G. Porzi in: J. Org. Chem. 1981, 46, 8, 1759-1760.
^ D. Yang, G. Zuccarello, BR Mattes in: Macromolecules 2002, 35, 13, 5304-5313.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on hexamethyleneimine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[CRC90_3_280-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-280.

[3] L. Ruzicka, M. Kobelt, O. Hafliger, V. Prelog in: Helvetica Chimica Acta 1949, 32, 544–552.

[4] SR Wann, PT Thorsen, MM Kreevoy in: J. Org. Chem. 1981, 46, 12, 2579-2581.

[5] Bui-The-Khai, C. Concilio, G. Porzi in: J. Org. Chem. 1981, 46, 8, 1759-1760.

[6] D. Yang, G. Zuccarello, BR Mattes in: Macromolecules 2002, 35, 13, 5304-5313.