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Sigma-Aldrich

(±)-trans-1,2-Diaminocyclohexane

99%

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Synonym(s):
(±)-trans-1,2-Cyclohexanediamine
Linear Formula:
C6H10(NH2)2
CAS Number:
1121-22-8
Molecular Weight:
114.19
Beilstein:
3193807
MDL number:
MFCD00063747
PubChem Substance ID:
24856187
NACRES:
NA.22

vapor pressure

0.4 mmHg ( 20 °C)

Quality Level

200

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

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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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

156.2 °F - closed cup

Flash Point(C)

69 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
Enantiopure Monoprotected cis-1, 2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis
A Berkessel, et al
ChemCatChem, 2, 1215-1218 (2010)
Tetrahedron, 49, 4419-4419 (1993)
trans-1, 2-Diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: applications in asymmetric synthesis and molecular recognition
YL Bennani, et al.
Chemical Reviews, 97, 3161-3196 null
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