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270016

Sigma-Aldrich

(±)-trans-1,2-Diaminocyclohexane

99%

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

vapor pressure

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

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This Item
346721421804346713
form

liquid

form

solid

form

-

form

solid

refractive index

n20/D 1.489 (lit.)

refractive index

-

refractive index

-

refractive index

-

bp

79-81 °C/15 mmHg (lit.)

bp

-

bp

-

bp

104-110 °C/40 mmHg (lit.)

mp

14-15 °C (lit.)

mp

-

mp

107-109 °C (lit.)

mp

40-43 °C (lit.)

density

0.951 g/mL at 25 °C (lit.)

density

-

density

-

density

-

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

Signal Word

Danger

Hazard Statements

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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Customers Also Viewed

Slide 1 of 2

1 of 2

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
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
Chirality, 4, 447-447 (1992)
Tetrahedron, 49, 4419-4419 (1993)
Enantiopure Monoprotected cis-1, 2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis
A Berkessel, et al
ChemCatChem, 2, 1215-1218 (2010)

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