270016
(±)-trans-1,2-Diaminocyclohexane
99%
Synonyme(s) :
(±)-trans-1,2-Cyclohexanediamine
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A propos de cet article
Formule linéaire :
C6H10(NH2)2
Numéro CAS:
Poids moléculaire :
114.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3193807
Assay:
99%
Form:
liquid
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0.4 mmHg ( 20 °C)
Quality Level
assay
99%
form
liquid
refractive index
n20/D 1.489 (lit.)
bp
79-81 °C/15 mmHg (lit.)
mp
14-15 °C (lit.)
density
0.951 g/mL at 25 °C (lit.)
SMILES string
N[C@@H]1CCCC[C@H]1N
InChI
1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m1/s1
InChI key
SSJXIUAHEKJCMH-PHDIDXHHSA-N
General description
(±)-trans-1,2-Diaminocyclohexane is widely used as a ligand in coordination chemistry and organocatalysis. It also serves as an achiral ligand in asymmetric catalysis. (±)-trans-1,2-Diaminocyclohexane was condensed with aliphatic dialdehydes to form [3+3] or [2+2] macrocyclization products.
Application
(±)-trans-1,2-Diaminocyclohexane was used in the synthesis of macrocyclic [3+3] hexa Schiff base. It was also employed in the synthesis of multidentate ligands, chiral auxiliaries and chiral stationary phases.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Classe de stockage
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
156.2 °F - closed cup
flash_point_c
69 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Marcin Kwit et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(31), 8688-8695 (2007-07-31)
Aliphatic dialdehydes of rigid structures having a cyclohexane, a bicyclo[2.2.2]octane or a [7]triangulane skeleton, have been condensed with enantiomerically pure trans-1,2-diaminocyclohexane to give [3+3] or [2+2] macrocyclization products. Unlike acyclic aliphatic imines, these macrocyclic oligoimines show enhanced stabilities and their
Jana Hodacová et al.
Organic letters, 9(26), 5641-5643 (2007-11-22)
2,2'-Bipyridine-5,5'-dicarbaldehyde has been prepared in two steps by enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. On condensation of this dialdehyde with enantiomerically pure trans-1,2-diaminocyclohexane, the macrocyclic [3+3] hexa Schiff base
Enantiopure Monoprotected cis-1, 2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis
A Berkessel, et al
ChemCatChem, 2, 1215-1218 (2010)