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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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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
(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)
Jana Kasparkova et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(4), 1330-1341 (2007-11-21)
The different antitumor and other biological effects of the third-generation antitumor platinum drug oxaliplatin [(1R,2R-diamminocyclohexane)oxalatoplatinum(II)] in comparison with those of conventional cisplatin [cis-diamminedichloridoplatinum(II)] are often explained by the ability of oxaliplatin to form DNA adducts of different conformation and consequently
Cristina Nativi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(17), 4814-4820 (2011-03-10)
A new generation of chiral tripodal receptors for recognition of carbohydrates, featuring trans-1,2-diaminocyclohexane as a key structural element, and their recognition properties toward a set of glycosides of biologically relevant monosaccharides is described. The introduction of a chelating diamino unit
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