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346721

Sigma-Aldrich

(1R,2R)-(−)-1,2-Diaminocyclohexane

98%

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Synonym(s):
(1R)-trans-1,2-Cyclohexanediamine
Linear Formula:
C6H10(NH2)2
CAS Number:
20439-47-8
Molecular Weight:
114.19
Beilstein:
2801643
MDL number:
MFCD00062985
PubChem Substance ID:
24861433
NACRES:
NA.22

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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This Item
270016127027346713
(1R,2R)-(−)-1,2-Diaminocyclohexane 98%

Sigma-Aldrich

346721

(1R,2R)-(−)-1,2-Diaminocyclohexane

(±)-trans-1,2-Diaminocyclohexane 99%

Sigma-Aldrich

270016

(±)-trans-1,2-Diaminocyclohexane

N-Methyl-1,3-diaminopropane 98%

Sigma-Aldrich

127027

N-Methyl-1,3-diaminopropane

(1S,2S)-(+)-1,2-Diaminocyclohexane 98%

Sigma-Aldrich

346713

(1S,2S)-(+)-1,2-Diaminocyclohexane

form

solid

form

liquid

form

-

form

solid

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

optical activity

[α]20/D −25°, c = 5 in 1 M HCl

optical activity

-

optical activity

-

optical activity

[α]20/D +25°, c = 5 in 1 M HCl

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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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)
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 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)
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.
Mukaiyama, T.
Aldrichimica Acta, 29, 59-59 (1996)
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