132551

Sigma-Aldrich

1,2-Diaminocyclohexane, mixture of cis and trans

99%

Synonym(s):
1,2-Cyclohexanediamine, DHC 99
Linear Formula:
C6H10(NH2)2
CAS Number:
Molecular Weight:
114.19
Beilstein/REAXYS Number:
506142
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor pressure

0.4 mmHg ( 20 °C)

assay

99%

refractive index

n20/D 1.49 (lit.)

bp

92-93 °C/18 mmHg (lit.)

density

0.931 g/mL at 25 °C (lit.)

SMILES string

NC1CCCCC1N

InChI

1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2

InChI key

SSJXIUAHEKJCMH-UHFFFAOYSA-N

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General description

1,2-Diaminocyclohexane undergoes non-templated reaction with homochiral as well as the racemic form of trans-1,2-diaminocyclohexane with terephthaldehyde to yield (3+3)-cyclocondensed molecular triangles. It acts as ligand and forms organotin complexes, having potential applications as metal-based antitumour drugs.

Application

1,2-Diaminocyclohexane was used in the synthesis of chiral ruthenium(IV)-oxo complexes.

Packaging

18 L in VerSA-Flow™
1 L in glass bottle
50, 250 mL in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2735PSN2 8 / PGIII

WGK Germany

WGK 1

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

(3+ 3)-Cyclocondensation of the enantiopure and racemic forms of trans-1, 2-diaminocyclohexane with terephthaldehyde. Formation of diastereomeric molecular triangles and their stereoselective solid-state stacking into microporous chiral columns.
Chadim M, et al.
Tetrahedron Asymmetry, 12(1), 127-133 (2001)
J J Bonire et al.
Journal of inorganic biochemistry, 83(2-3), 217-221 (2001-03-10)
Platinum compounds containing the ligand 1,2-diaminocyclohexane (DACH) such as tetraplatin [PtCl4(DACH)] have been found to be active in cisplatin-resistant tumour models. In an attempt to develop novel metal-based drugs with a different therapeutic profile to cisplatin, we have synthesised a...
Chiral ruthenium (IV)-oxo complexes. Structure, reactivities of [Ru (terpy)(Nn N) O]2+Nn N= N, N, N', N'-tetramethyl-1, 2-diaminocyclohexane) and [Ru (Me3 tacn)(cbpy) O]2+ (cbpy=(-)-3, 3'-[(4 S-trans)-1, 3-dioxolane-4, 5-dimethyl]-2, 2'-bipyridine).
Cheng WC, et al.
Inorgorganica Chimica Acta, 242(1), 105-113 (1996)
Hidekazu Yamada et al.
Journal of the American Chemical Society, 134(17), 7250-7253 (2012-04-18)
Optically active amidine dimer strands having a variety of chiral and achiral linkers with different stereostructures are synthesized and used as templates for diastereoselective imine-bond formations between two achiral carboxylic acid monomers bearing a terminal aldehyde group and racemic 1,2-cyclohexanediamine...
Yu He et al.
Inorganic chemistry, 50(24), 12651-12660 (2011-11-11)
Iron complexes with the tetradentate N-donor ligand N,N'-di(phenylmethyl)-N,N'-bis(2-pyridinylmethyl)-1,2-cyclohexanediamine (bbpc) are reported. Despite the benzyl groups present on the amines, the iron compounds catalyze the oxygenation of cyclohexane to an extent similar to those employing less sterically encumbered ligands. The catalytic...

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