15827-56-2

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C6H14N2/c7-5-1-2-6(8)4-3-5/h5-6H,1-4,7-8H2/t5-,6+

Upstream product

• 556-48-9 1,4-Cyclohexanediol 
• 3114-70-3 trans-1,4-diaminocyclohexane 
• 100-02-7 4-nitro-phenol 
• 637-88-7 1,4-Cyclohexanedione 
• 106-50-3 1,4-phenylenediamine 
• 32222-08-5 cis-1.4-bis-methoxycarbonylamino-cyclohexane 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 113282-19-2 cis-1,4-dibenzylideneaminocyclohexane 
• 117596-27-7 cis-1,4-dibenzoylaminocyclohexane 
• 1388891-42-6 (1s,4s)-1-N-methyl-4-N-[7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]cyclohexane-1,4-diamine 
• 1388891-36-8 (1s,4s)-N₁-(6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-yl)cyclohexane-1,4-diamine 
• 2840-91-7 cis-cyclohexane-1,4-diacetamide 
• 181760-73-6 N-(5-Chloro-pyrimidin-2-yl)-N'-{4-[N'-(5-chloro-pyrimidin-2-yl)-guanidino]-cyclohexyl}-guanidine 
• 61366-98-1 1-(2-Chloro-ethyl)-3-{4-[3-(2-chloro-ethyl)-ureido]-cyclohexyl}-urea 

Relevant academic research and scientific papers

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

The Rhodium Catalysed Direct Conversion of Phenols to Primary Cyclohexylamines

Cyclohexylamines are important intermediates in chemical industry, which are currently produced from petrochemical sources. Phenols, however, are an attractive sustainable feedstock. We here demonstrate the transformation of phenols with ammonia to primary cyclohexylamines. In contrast to previously reported chemistry which used palladium catalysts, we here show that rhodium is an excellent catalyst for the formation of primary cyclohexylamines. Different parameters were studied and it was shown that the reaction is applicable to a scope of phenolic compounds providing high selectivity.

PRODUCTION METHOD OF TRANS-DIAMINOCYCLOHEXANE

PROBLEM TO BE SOLVED: To provide a method to gain a trans isomer by isomerization from a cis isomer of diaminocyclohexane efficiently. SOLUTION: When a cis isomer of diaminocyclohexane (including 1,4-diaminocyclohexane) is isomerized under presence of metal catalyst (including ruthenium-catalyst) and a trans isomer of the diaminocyclohexane is provided, the cis isomer is performed heating and pressure treatment in inert gas (including nitrogen gas). In such the isomerization processing, a reaction temperature can be more than 100°C (e.g., around 150-250°C), and a pressure of the inert gas can be more than 5 MPa (e.g., 7-20 MPa). COPYRIGHT: (C)2015,JPOandINPIT

Catalytic hydrogenation of 1,4-phenylenediamine to 1,4-cyclohexanediamine

Catalytic hydrogenation of 1,4-phenylenediamine to 1,4-cyclohexanediamine using Ru/Al2O3 as a catalyst was carried out in water, and the results were compared with those in isopropanol and SC-CO2. 80% 1,4-phenylenediamine conversion with 87% selectivity to 1,4-cyclohexanediamine was achieved on 5% Ru/Al2O3 catalyst at 90°C and H2 pressure of 4 MPa. The hydrogenation of 1,4-phenylenediamine is influenced by the solvent. A systematic study of the hydrogenation of 1,4-phenylenediamine revealed that the reaction was consecutive. The longer the time, the lower was the CHDA selectivity. Also, the reaction temperature was an important parameter and played a vital role in preventing the formation of side products. Pleiades Publishing, Ltd., 2014.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.