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132551

Sigma-Aldrich

1,2-Diaminocyclohexane, mixture of cis and trans

99%

Synonym(s):

1,2-Cyclohexanediamine, DHC 99

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About This Item

Linear Formula:
C6H10(NH2)2
CAS Number:
694-83-7
Molecular Weight:
114.19
Beilstein:
506142
EC Number:
211-776-7
MDL number:
MFCD00001491
UNSPSC Code:
12352100
PubChem Substance ID:
24848059
NACRES:
NA.22

vapor pressure

0.4 mmHg ( 20 °C)

Assay

99%

form

liquid

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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(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)
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)
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
Robert Häner et al.
Journal of the American Chemical Society, 132(21), 7466-7471 (2010-05-13)
Oligopyrenotides, abiotic oligomers that exhibit significant structural analogies to the nucleic acids, are described. They are composed of achiral, phosphodiester-linked pyrene building blocks and a single chiral 1,2-diaminocyclohexane unit. These oligomers form stable hybrids in aqueous solution. Hybridization is based
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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