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Merck
CN

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:
20439-47-8
Molecular Weight:
114.19
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
24861433
MDL number:
MFCD00062985
Beilstein/REAXYS Number:
2801643

Key Documents

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Product Name

(1R,2R)-(−)-1,2-Diaminocyclohexane, 98%

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

200

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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.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000508728
0000508728
0000502521
0000502521
0000473156

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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)
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.
Chenier, P.J. et al.
Tetrahedron Letters, 38, 7341-7341 (1997)
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