(R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine

Name: (R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine
Brand: ALDRICH

≥97.0% (GC)

Synonym(s):

(R,R)-(−)-N,N′-Dimethyl-1,2-diaminocyclohexane, trans-1,2-Bis(methylamino)cyclohexane

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About This Item

Empirical Formula (Hill Notation):

C₈H₁₈N₂

CAS Number:

68737-65-5

Molecular Weight:

142.24

NACRES:

NA.22

PubChem Substance ID:

24885095

UNSPSC Code:

12352116

MDL number:

MFCD00671527

Assay:

≥97.0% (GC)

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Properties

Quality Level

200

assay

≥97.0% (GC)

optical activity

[α]/D -145±5°, c = 4.47 in chloroform

mp

39-44 °C

functional group

amine

storage temp.

2-8°C

SMILES string

CN[C@@H]1CCCC[C@H]1NC

InChI

1S/C8H18N2/c1-9-7-5-3-4-6-8(7)10-2/h7-10H,3-6H2,1-2H3/t7-,8-/m1/s1

InChI key

JRHPOFJADXHYBR-HTQZYQBOSA-N

Description

General description

(R,R)-(-)-N,N′-Dimethyl-1,2-cyclohexanediamine is a N,N′-dimethylated derivative of enantiopure 1,2-diaminocyclohexane. It can be formed during the hydrolysis of (R_3a,R_7a)-1,3-(dimethyl)-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide using HCl-methanol.

Application

(R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine can be used:

As a ligand in the preparation of 4H-benzo[f]imidazo[1,4]diazepin-6-one through multi-component Ullmann coupling reaction.
In one of the key synthetic steps for the preparation of tricyclic γ-secretase modulators.
To prepare chiral fluorous diamino-diol proligand, which is used in the synthesis of zirconium metal complexes applicable as catalysts in 1-hexene polymerization.