(1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

Base Information

• Chemical Name: (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine
• CAS No.: 67579-81-1
• Molecular Formula: C8H18 N2
• Molecular Weight: 142.244
• Hs Code.: 2921309990
• European Community (EC) Number: 614-082-6,626-704-3
• DSSTox Substance ID: DTXSID20986938
• Nikkaji Number: J596.263C
• Wikidata: Q72469663
• Mol file: 67579-81-1.mol

Synonyms:trans-N,N'-dimethyl-1,2-cyclohexanediamine

Chemical Property of (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

Chemical Property:

• Melting Point: 4°C
• Refractive Index: n20/D1.472(lit.)
• Boiling Point: 83 °C / 13mmHg
• PKA: 11.04±0.40(Predicted)
• Flash Point: 60℃
• PSA: 24.06000
• Density: 0.89
• LogP: 1.51820
• Storage Temp.: Refrigerator
• Sensitive.: air sensitive
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.146998583
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99.9% ^*data from raw suppliers

trans-(1R,2R)-N,N’-Bismethyl-1,2-cyclohexanediamine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 36/37/38-34-22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCCCC1NC
• Isomeric SMILES: CN[C@@H]1CCCC[C@H]1NC
• 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. 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 bromidesN-arylpyridones obtained via reaction between 2-substituted pyridines and aryl halidesN-aryl amines obtained via reaction between amines and aryl iodides/aryl bromides
• Description: Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine is a useful research chemical for organic synthesis and other chemical processes.

Technology Process of (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine

There total 17 articles about (1R,2R)-(-)-N,N'-Dimethylcyclohexane-1,2-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

N,N’-[(±)-trans-cyclohexane-1,2-diyl]diformamide → trans-N,N'-dimethylcyclohexane-1,2-diamine (61798-24-1,67579-81-1,68737-65-5,75599-23-4,87583-89-9,99295-66-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 16h;

DOI:10.1021/ja027433h

Reference yield: 88.0%

trans-1,2-bis(ethoxycarbonylamino)cyclohexane → trans-N,N'-dimethyl-1,2-cyclohexyldiamine (67579-81-1)

Guidance literature:

trans-1,2-bis(ethoxycarbonylamino)cyclohexane; With lithium aluminium tetrahydride; In tetrahydrofuran; at 5 - 20 ℃; Heating / reflux;

With sodium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 1h; Heating / reflux;

Reference yield: 42.0%

trans-N,N'-dimethylcyclohexane-1,2-diamine (61798-24-1,67579-81-1,68737-65-5,75599-23-4,87583-89-9,99295-66-6) → (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane (61798-24-1,67579-81-1,68737-65-5,75599-23-4,99295-66-6,87583-89-9)

Guidance literature:

trans-N,N'-dimethylcyclohexane-1,2-diamine; With L-Tartaric acid; In ethanol; at 20 ℃; for 1h; Reflux; Resolution of racemate;

With potassium hydroxide; In dichloromethane; at 20 ℃; pH=9-10; Reflux; Resolution of racemate;

DOI:10.3184/174751913X13626731204890

upstream raw materials:

(S,S)-1,2-diaminocyclohexane-N,N'-diethyl carbamate

N-((1S,2S)-2-Formylamino-cyclohexyl)-formamide

(S,S)-1,2-diaminocyclohexane

7-methyl-7-azabicyclo[4.1.0]heptane

Downstream raw materials:

N-(2-pyridyl)indole

1-phenyl-1H-indole

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

(1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane

Refernces

• 1、 Shen, Yan-Hong,Ye, Qing,Hou, Shao-Gang,Wang, Qun. "An efficient synthesis of enantiomerically pure trans-N1,N 2-dimethylcyclohexane-1,2-diamine". . p. 191 - 192. Retrieved 2013/07/27.
• 2、 -. "Method for catalytic preparation of hydromorphone and hydrocodone". Page/Page column 7-8. . Retrieved 2008/12/06.