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

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

Used in Catalysts for N-Amidation and N-Arylation:
TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE is used as a catalyst component in the N-amidation of aryl and heteroaryl iodides, bromides, and sometimes unactivated aryl chlorides, in conjunction with CuI. This catalyst system is known for its generality and high efficiency, facilitating the formation of amide bonds in organic synthesis.
Additionally, TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE is used for the N-arylation of indoles, further expanding its applications in organic chemistry.
Used in Ligand for Copper-Catalyzed C-N Coupling Reactions:
TRANS-1,2-BIS(METHYLAMINO)CYCLOHEXANE serves as a ligand in copper-catalyzed C-N coupling reactions, enabling the synthesis of various products such as:
1. Vinylsulfoximines: Obtained from NH sulfoximes and vinyl bromides, these compounds find applications in the pharmaceutical industry and as intermediates in the synthesis of complex molecules.
2. N-Arylpyridones: Produced via the reaction between 2-substituted pyridines and aryl halides, these compounds are valuable in the development of pharmaceuticals and agrochemicals.
3. N-Aryl amines: Derived from the reaction between amines and aryl iodides/aryl bromides, N-aryl amines are important building blocks in the synthesis of various organic compounds, including pharmaceuticals and dyes.

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 20431-81-6 rac-trans-2-methylamino-cyclohexanol 
• 61798-24-1 trans-N,N'-dimethylcyclohexane-1,2-diamine 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 51066-08-1 7-methyl-7-azabicyclo[4.1.0]heptane 
• 74-89-5 methylamine 
• 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

• 68737-65-5 (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 61798-24-1 (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 40619-61-2 2-(1-N-phenyl-1H-indol-3-yl)ethan-1-amine 
• 883-39-6 1-phenyl-1H-benzotriazole 
• 473918-48-8 N-(2-aminophenyl)indole 
• 174621-50-2 1-(4-ethoxycarbonylphenyl)indole 
• 16096-33-6 1-phenyl-1H-indole 
• 3419-91-8 N-(2-pyridyl)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.

An efficient synthesis of enantiomerically pure trans-N1,N 2-dimethylcyclohexane-1,2-diamine

A new pathway is described to produce a highly optically pure isomer of trans-N1,N2-dimethylcyclohexane-1,2-diamine through four simple steps. Reaction of cyclohexene oxide with aqueous methylamine, followed by cyclisation with Mitsunobu reagent and ring-opening reactions gave rac-trans-N1,N2-dimethylcyclohexane-1,2-diamine, and the enantiomers were obtained via a kinetic resolution using tartaric acid.

Method for catalytic preparation of hydromorphone and hydrocodone

The present invention generally relates to catalysts of formula (III) [in-line-formulae][M(P(Ra)(Rb)N(Rc)(Rd))2Xn]mYp [/in-line-formulae]that selectively convert morphine/codeine to hydromorphone/hydrocodone, and methods of use thereof.

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

The copper-catalyzed N-arylation of indoles

A general method for the N-arylation of indoles using catalysts derived from Cul and trans-1,2-cyclohexanediamine (1a), trans-N,N′-dimethyl-1,2-cyclohexanediamine (2a), or N,N′-dimethyl-ethylenediamine (3) is reported. N-Arylindoles can be produced in high yield from the coupling of an aryl iodide or aryl bromide with a variety of indoles.

The asymmetric synthesis of α-substituted α-methyl and α-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides

The design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described. In the case of α-ethyl and α-benzyl phosphonamides, the geometry of both the secondary and tertiary carbanions was determined to be planar through deprotonation/deuteration/alkylation experiments. Stereoselective alkylations of such systems proceeded in good yields and with high diastereoselectivities. The resulting α,α-alkylated phosphonamides were hydrolyzed to give the corresponding α,α-alkyl phosphonic acids with high degrees of enantiomeric purity.

Synthesis and characterization of both enantiomers of a chiral C60 derivative with C2 symmetry

The addition of chiral diamines to C60 allows the synthesis of the two enantiomers of a chiral C60 derivative with C2 symmetry. The circular dichroism spectra of the two isomers show a very intense chirospectroscopic response.

211. Scope and Limitations of the Reductive Coupling of Aromatic Aldimine Derivatives with Formation of 1,2-Diarylethylenediamine Units, Using Low-Valent Titanium Reagents

Besides the adducts from lithium amides to aromatic aldehydes, iminium salts, aminals, and N-silylimines of aromatic aldehydes are coupled by the black suspension obtained from TiCl4 and Mg turnings in tetrahydrofuran (THF).The 1,2-diarylethylenediamines with tertiary and primary amino groups thus obtained are formed with no or only moderate diastereoselectivity (products 4a-d (Scheme 2) and 5a-e (Scheme 3), respectively); the amine component may contain a strained ring or additional heteroatoms as in azetidin, bis(2-metoxyethyl)amine piperazine, morpholine, and thiomorpholine (products 6a-e; Table 1).By an in-situ procedure, ethylenediamines and propane-1,3-diamines with two secondary amino groups are cyclized with aromatic aldehydes to give exclusively trans-diaryl-substituted piperazine and perhydro-1,4-diazepine derivatives (products 7a-f; Table 2).Enantiomerically pure monocyclic trans,cis-5-alkyl-2,3-diaryl-piperazines and diazabicyclononanes and -decanes are obtained by employing suitable diamines prepared from the amino acids (S)-alanine, (S)-phenylalanine, (S)-proline, and from (S,S)- or (R,R)-cyclohexane-1,2-diamine, respectively (products 11a-i, 7e; Table 4).The configurations of all products are derived from the high-field NMR spectra, some of which are discussed in detail (Figs. 1 and 2, Tables 3 and 5); all new compounds are fully characterized by their physical data.Depending upon the structure of the components employed, the yields of purified products range from as low as 7percent to essentially quantitative.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.