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346713

Sigma-Aldrich

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

98%

Synonym(s):

(1S)-trans-1,2-Cyclohexanediamine, (1S)-trans-1,2-Diaminocyclohexane

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About This Item

Linear Formula:
C6H10(NH2)2
CAS Number:
21436-03-3
Molecular Weight:
114.19
Beilstein:
2801645
MDL number:
MFCD00062986
UNSPSC Code:
12352116
PubChem Substance ID:
24861431
NACRES:
NA.22

Assay

98%

form

solid

optical activity

[α]20/D +25°, c = 5 in 1 M HCl

optical purity

ee: 99% (GLC)

bp

104-110 °C/40 mmHg (lit.)

mp

40-43 °C (lit.)

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-/m0/s1

InChI key

SSJXIUAHEKJCMH-WDSKDSINSA-N

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Application

Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Chenier, P.J. et al.
Tetrahedron Letters, 38, 7341-7341 (1997)
Kenji Yoshikawa et al.
Bioorganic & medicinal chemistry, 17(24), 8206-8220 (2009-11-04)
A series of cis-1,2-diaminocyclohexane derivatives were synthesized with the aim of optimizing previously disclosed factor Xa (fXa) inhibitors. The exploration of 5-6 fused rings as alternative S1 moieties resulted in two compounds which demonstrated improved solubility and reduced food effect
Hidekazu Yamada et al.
Journal of the American Chemical Society, 134(17), 7250-7253 (2012-04-18)
Optically active amidine dimer strands having a variety of chiral and achiral linkers with different stereostructures are synthesized and used as templates for diastereoselective imine-bond formations between two achiral carboxylic acid monomers bearing a terminal aldehyde group and racemic 1,2-cyclohexanediamine
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