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Merck

270016

(±)-trans-1,2-Diaminocyclohexane

99%

Synonym(s):

(±)-trans-1,2-Cyclohexanediamine

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About This Item

Linear Formula:
C6H10(NH2)2
CAS Number:
1121-22-8
Molecular Weight:
114.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24856187
MDL number:
MFCD00063747
Beilstein/REAXYS Number:
3193807
Assay:
99%
Form:
liquid

Key Documents

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InChI

1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m1/s1

SMILES string

N[C@@H]1CCCC[C@H]1N

InChI key

SSJXIUAHEKJCMH-PHDIDXHHSA-N

vapor pressure

0.4 mmHg ( 20 °C)

assay

99%

form

liquid

Quality Level

200

bp

79-81 °C/15 mmHg (lit.)

mp

14-15 °C (lit.)

density

0.951 g/mL at 25 °C (lit.)

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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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

156.2 °F - closed cup

flash_point_c

69 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4760
SDBB0771
STBK8456
STBK2876
STBJ5537

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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
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)
Chirality, 4, 447-447 (1992)
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