346721
(1R,2R)-(−)-1,2-Diaminocyclohexane
98%
Synonym(s):
(1R)-trans-1,2-Cyclohexanediamine
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About This Item
Linear Formula:
C6H10(NH2)2
CAS Number:
Molecular Weight:
114.19
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2801643
Assay:
98%
Form:
solid
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
assay
98%
form
solid
optical activity
[α]20/D −25°, c = 5 in 1 M HCl
Quality Level
Related Categories
Application
Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.
(1R,2R)-(-)-1,2-Diaminocyclohexane may be used to prepare:
- Chiral C2-symmetric diphenylphosphoramide and diphenylthiophosphoramide ligands by reacting with diphenylphosphinic chloride and diphenylthiophosphinic chloride, respectively.
- Bis-urea and the amino-thiourea ligands by reacting with isocyanates and isothiocyanates, respectively.
- Biologically active chiral palladium(II) and platinum(II) complexes.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
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Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
158.0 °F - closed cup
flash_point_c
70 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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C 2-Symmetric diphenylphosphoramide and diphenylthiophosphoramide derived from (1R, 2R)-1, 2-diaminocyclohexane as ligands for the titanium (IV) alkoxide-promoted addition of diethylzinc to aldehydes.
Shi M and Sui WS
Tetrahedron Asymmetry, 10(17), 3319-3325 (1999)
Chiral amino-urea derivatives of (1R, 2R)-1, 2-diaminocyclohexane as ligands in the ruthenium catalysed asymmetric reduction of aromatic ketones by hydride transfer.
Bied C, et al.
Tetrahedron Asymmetry, 12(2), 329-336 (2001)
Design principles of chiral carbon nanodots help convey chirality from molecular to nanoscale level.
Luka Ðorđević et al.
Nature communications, 9(1), 3442-3442 (2018-08-26)
The chirality of (nano)structures is paramount in many phenomena, including biological processes, self-assembly, enantioselective reactions, and light or electron spin polarization. In the quest for new chiral materials, metallo-organic hybrids have been attractive candidates for exploiting the aforementioned scientific fields.
Chiral palladium (II) and platinum (II) complexes of diaminocyclohexane: X-ray structures of (1R, 2R)-(-)-1, 2-diaminocyclohexane dihydrochloride and its corresponding oxalato platinum (II) complex.
Abu-Surrah AS, et al.
Polyhedron, 22(12), 1529-1534 (2003)
Mukaiyama, T.
Aldrichimica Acta, 29, 59-59 (1996)
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