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346721

Sigma-Aldrich

(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
Beilstein:
2801643
MDL number:
MFCD00062985
UNSPSC Code:
12352116
PubChem Substance ID:
24861433
NACRES:
NA.22

Quality Level

200

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBX1621
BCBV8403
BCBT1015
BCBR5574V
BCBR3705V

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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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