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| | Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine Basic information | | Uses |
| Product Name: | Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine | | Synonyms: | trans-(1R,2R)-N,N'-BisMethyl-1,2-cyclohexanedia;trans-N,N'-DiMethylcyclohexane-1,2-diaMin;rel-(1R,2R)-N1,N2-DiMethylcyclohexane-1,2-diaMine;(1R,2R)-rel-N1,N2-DiMethylcyclohexane-1,2-diaMine;TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE;trans-N,N'-Dimethyl-1,2-cyclohexanediamine,98%;TRANS-N,N''-DIMETHYL-1,2-CYCLOHEXANEDIAMINE;(1R,2R)-rel-N1,N2-Dimethyl-1,2-cyclohexanediamine | | CAS: | 67579-81-1 | | MF: | C8H18N2 | | MW: | 142.24 | | EINECS: | | | Product Categories: | Chiral Nitrogen;DACH&Trost Series;Chiral Reagents;Miscellaneous Reagents | | Mol File: | 67579-81-1.mol |  |
| | 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.) | | Fp | 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) |
| 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 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Acute Tox. 4 Oral
Eye Dam. 1
Skin Corr. 1B |
| | 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.
| | References | [1] Patent: CN106478431, 2017, A. Location in patent: Paragraph 0011; 0012; 0013; 0014; 0015; 0016; 0017; 0018 |
| | Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine Preparation Products And Raw materials |
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