67579-81-1

Basic information

• Product Name: TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE
• Synonyms: TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE;TRANS-N,N'-DIMETHYLCYCLOHEXANE-1,2-DIAMINE;trans-N,N'-Dimethyl-1,2-cyclohexanediamine,98%;TRANS-N,N''-DIMETHYL-1,2-CYCLOHEXANEDIAMINE;(1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine;(1R,2R)-rel-N1,N2-Dimethyl-1,2-cyclohexanediamine;trans-N,N'-DiMethylcyclohexane-1,2-diaMin;(+/-)-trans-1,2-Diamino-N,N'-dimethylcyclohexane
• CAS NO: 67579-81-1
• Molecular Formula: C₈H₁₈N₂
• Molecular Weight: 142.24
• Product Categories: Chiral Reagents;Miscellaneous Reagents;Chiral Nitrogen;DACH&Trost Series
• Mol File: 67579-81-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 4°C
• Boiling Point: 83 °C / 13mmHg
• Flash Point: 60℃
• Appearance: colorless to pale yellow/liquid
• Density: 0.89
• Refractive Index: n20/D1.472(lit.)
• Storage Temp.: Refrigerator
• PKA: 11.04±0.40(Predicted)
• Sensitive: air sensitive
• CAS DataBase Reference: TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE(67579-81-1)
• EPA Substance Registry System: TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE(67579-81-1)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: 2735
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 67579-81-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 67579-81-1 differently. You can refer to the following data:
1. 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.
2. 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.

Upstream product

• 20431-81-6 rac-trans-2-methylamino-cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 51066-08-1 7-methyl-7-azabicyclo[4.1.0]heptane 
• 74-89-5 methylamine 
• 61798-24-1 trans-N,N'-dimethylcyclohexane-1,2-diamine 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 122743-11-7 N-((1S,2S)-2-Formylamino-cyclohexyl)-formamide 
• 942606-10-2 (S,S)-1,2-diaminocyclohexane-N,N'-diethyl carbamate 

Downstream Products

• 3419-91-8 N-(2-pyridyl)indole 
• 16096-33-6 1-phenyl-1H-indole 
• 68737-65-5 (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 61798-24-1 (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 515124-12-6 N1,N2?dimethyl?N1,N2?bis(pyridin?2?ylmethyl)cyclohexane?1,2?diamine 
• 473918-48-8 N-(2-aminophenyl)indole 
• 174621-50-2 1-(4-ethoxycarbonylphenyl)indole 
• 132076-20-1 (3aS,7aS)-2<(1S)-methyl-2-phenylethyl>-<3a,4,5,6,7,7a-octahydro-1,3-dimethyl-1,3,2-benzodiazaphosphole>-2-oxide 
• 132076-19-8 (3aS,7aS)-2<(1R)-methyl-2-phenylethyl>-<3a,4,5,6,7,7a-octahydro-1,3-dimethyl-1,3,2-benzodiazaphosphole>-2-oxide 

Relevant articles and documents

Method for synthesizing trans-cyclohexanedimethanamine

The invention discloses a method for synthesizing trans-cyclohexanedimethanamine, comprising steps of reacting cyclohexene oxide and methylamine aqueous solution under the catalysis of boric acid, and then adding sulfuric acid, dewatering to form an ester, ring-closing under alkaline conditions, adding methylamine aqueous solution and boric acid for hermetic reaction, and distilling to obtain trans-cyclohexanedimethanamine. The synthetic process is simple to perform, provides facilitated isolation and purification and high yield and product purity, and is suitable for batch production.

On the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine: Probing the effect of the stoichiometric ligand

(Chemical Equation Presented) To map out the stoichiometric ligand requirements in the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine, 24 different ligands have been evaluated; the highest enantioselectivity (90:10 er) was obtained by using s-BuLi in the presence of 0.3 equiv of (-)-sparteine and 1.3 equiv of a cyclohexanediamine-derived ligand.

The role of chelating diamine ligands in the Goldberg reaction: A kinetic study on the copper-catalyzed amidation of aryl iodides

The mechanistic details of the Cu-catalyzed amidation of aryl iodides are presented. The kinetic data suggest that the diamine ligand prevents multiple ligation of the amide. The formation of an amidocuprate species external to the catalytic cycle helped to rationalize the dependence on diamine concentration and the inverse dependence on amide concentration at low diamine concentrations. The intermediacy of a Cu(I) amidate was established through both its chemical and kinetic competency. Copyright