Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine Chemical Properties

Melting point:

4°C

Boiling point:

83 °C / 13mmHg

Density 

0.89

refractive index 

n20/D1.472(lit.)

Flash point:

60℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

liquid

pka

11.04±0.40(Predicted)

color 

colorless to pale yellow

Sensitive 

air sensitive

InChI

InChI=1/C8H18N2/c1-9-7-5-3-4-6-8(7)10-2/h7-10H,3-6H2,1-2H3/t7-,8-/s3

InChIKey

JRHPOFJADXHYBR-HTQZYQBOSA-N

SMILES

[C@@H]1(NC)CCCC[C@H]1NC |&1:0,7,r|

CAS DataBase Reference

67579-81-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

36/37/38-34-22

Safety Statements 

26-36/37/39-45

RIDADR 

2735

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

2921309990

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine Usage And Synthesis

Uses

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine used with CuI to form a general and highly efficient catalyst for the N-amidation of aryl and heteroaryl iodides, bromides and in some cases, unactivated aryl chlorides. The catalyst system is also used for the N-arylation of indoles.

Description

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine is a useful research chemical for organic synthesis and other chemical processes.

Uses

trans-N,N′-dimethylcyclohexane-1,2-diamine can be used as a ligand in the synthesis of the following products via copper catalyzed C-N coupling reactions:

• vinylsulfoximines obtained from NH sulfoximes and vinyl bromides
• N-arylpyridones obtained via reaction between 2-substituted pyridines and aryl halides
• N-aryl amines obtained via reaction between amines and aryl iodides/aryl bromides

Synthesis

Cyclohexene oxide (1) was reacted with 25–30% aqueous methylamine (1.5 equiv.) in a sealed reactor to form trans-2-(methylamino)cyclohexanol 2 at 80 °C within 5h. Compound 2 was subjected to Mitsunobu reaction at room temperature, followed by adjusting the pH from 2 to 10 to yield 7-methyl-7-azabicyclo[4.1.0]-heptane 3, which was directly subjected to the following reaction without purification. Ring-opening reactions of compound 3 with a methylamine aqueous solution were completed in a sealed reactor at 110 °C after 6h to yield Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine.

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine(67579-81-1)Related Product Information

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