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HomeProduct name listTrans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine

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

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

What is Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine?

Description

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

The Uses of Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine

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

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

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
CAS DataBase Reference 67579-81-1(CAS DataBase Reference)

Safety information for Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H314:Skin corrosion/irritation
Precautionary Statement Codes P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine

InChIKey JRHPOFJADXHYBR-HTQZYQBOSA-N
SMILES [C@@H]1(NC)CCCC[C@H]1NC |&1:0,7,r|

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