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
Beilstein/REAXYS Number:
2801643
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
98%
form
solid
optical activity
[α]20/D −25°, c = 5 in 1 M HCl
SMILES string
N[C@@H]1CCCC[C@H]1N
InChI
1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m1/s1
InChI key
SSJXIUAHEKJCMH-PHDIDXHHSA-N
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Application
(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.
Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.
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_germany
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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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)
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)
Chenier, P.J. et al.
Tetrahedron Letters, 38, 7341-7341 (1997)
Mukaiyama, T.
Aldrichimica Acta, 29, 59-59 (1996)
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