1,3-bis (aminomethyl) cyclohexane

Structural formula
	Structural formula without representation of the stereochemistry
General
Surname	1,3-bis (aminomethyl) cyclohexane
other names	1,3-cyclohexylbis (methylamine); 1,3-diaminomethylcyclohexane; C - (3-aminomethyl-cyclohexyl) -methylamine;
Molecular formula	C 8 H 18 N 2
Brief description	colorless liquid
External identifiers / databases
EC number	219-941-5
ECHA InfoCard	100.018.129
PubChem	17406
Wikidata	Q18455438
properties
Molar mass	142.24 g mol −1
Physical state	liquid
density	0.945 g cm −3
Melting point	−25 ° C
boiling point	240 ° C
Vapor pressure	34 Pa (25 ° C)
solubility	very light in water (> 1000 g / l)
Refractive index	1.493 (20 ° C)
safety instructions
H and P phrases	H: 302-312-314-412
	EUH: 210
	P: 264-273-280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
	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

1,3-bis (aminomethyl) cyclohexane (1,3-BAC) is a mixture of three stereoisomeric chemical compounds from the group of aliphatic amines .

When "1,3-bis (aminomethyl) cyclohexane" without in this article or in the scientific literature the name prefix is needed is always a mixture of equal parts of ( S , S ) form and ( R , R ) form and changing proportions of the meso form meant (see section stereochemistry).

presentation

1,3-bis (aminomethyl) cyclohexane can be prepared by hydrogenating various compounds, for example from m- xylylenediamine , from 1,3- benzenedicarbonitrile or from dicyanocyclohexane .

use

1,3-Bis (aminomethyl) cyclohexane is used industrially as a hardener for epoxy resins , as a raw material for the production of polyamides and isocyanates , as a rubber chemical, for paper processing agents , in fiber treatment agents and in cleaning agents.

Stereoisomers

1,3-bis (aminomethyl) cyclohexane contains two equally substituted stereocenters, consequently there are three stereoisomers:

( S , S ) -1,3-bis (aminomethyl) cyclohexane
( R , R ) -1,3-bis (aminomethyl) cyclohexane
meso -1,3-bis (aminomethyl) cyclohexane

The technical product is a mixture of these three isomers.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,3-bis (aminomethyl) cyclohexane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Data sheet 1,3-Cyclohexanebis (methylamine), mixture of isomers, 99% from Sigma-Aldrich , accessed on July 2, 2015 ( PDF ).
^ Leslie G. Humber: Agents Affecting Lipid Metabolism. XVI. The Synthesis of Analogs of trans-1,4-Bis (2-chlorobenzylaminomethyl) cyclohexane . In: Journal of Medicinal Chemistry . 8, No. 3, 1965, pp. 401-404. doi : 10.1021 / jm00327a033 .
↑ ^a ^b Patent EP1586554 : Purification of 1,3-bis (aminomethyl) cyclohexane by distillation. Published on October 19, 2005 , Inventors: Kazuhiko Amakawa, Kuniaki Muneyasu, Hiroshi Watanabe. ‌
^ Ha Q. Pham, Maurice J. Marks: Epoxy Resins . In: Ullmann's Encyclopedia of Industrial Chemistry . September, p. 192. doi : 10.1002 / 14356007.a09_547.pub2 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,3-bis (aminomethyl) cyclohexane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[Sigma-2] Data sheet 1,3-Cyclohexanebis (methylamine), mixture of isomers, 99% from Sigma-Aldrich , accessed on July 2, 2015 ( PDF ).

[3] Leslie G. Humber: Agents Affecting Lipid Metabolism. XVI. The Synthesis of Analogs of trans-1,4-Bis (2-chlorobenzylaminomethyl) cyclohexane . In: Journal of Medicinal Chemistry . 8, No. 3, 1965, pp. 401-404. doi : 10.1021 / jm00327a033 .

[:0-4] Patent EP1586554 : Purification of 1,3-bis (aminomethyl) cyclohexane by distillation. Published on October 19, 2005 , Inventors: Kazuhiko Amakawa, Kuniaki Muneyasu, Hiroshi Watanabe. ‌

[Ullmann-5] Ha Q. Pham, Maurice J. Marks: Epoxy Resins . In: Ullmann's Encyclopedia of Industrial Chemistry . September, p. 192. doi : 10.1002 / 14356007.a09_547.pub2 .