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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4282
MKCS7764
MKCV0418
MKCS0297
MKCM0592

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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)
Ran Feng et al.
Dalton transactions (Cambridge, England : 2003), 42(6), 2130-2145 (2012-11-29)
In this paper, the origins of enantioselectivity in asymmetric ketone hydrogenation catalyzed by RuH(2)(binap)(cydn) (cydn = trans-1,2-diaminocyclohexane) were discussed. Fifteen substrates involving aromatic, heteroaromatic, olefinic and dialkyl prochiral ketones were used to probe the catalytic mechanism and find an effective
Yu He et al.
Inorganic chemistry, 50(24), 12651-12660 (2011-11-11)
Iron complexes with the tetradentate N-donor ligand N,N'-di(phenylmethyl)-N,N'-bis(2-pyridinylmethyl)-1,2-cyclohexanediamine (bbpc) are reported. Despite the benzyl groups present on the amines, the iron compounds catalyze the oxygenation of cyclohexane to an extent similar to those employing less sterically encumbered ligands. The catalytic
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