cis-1,2-Diaminocyclohexane

Base Information

• Chemical Name: cis-1,2-Diaminocyclohexane
• CAS No.: 1436-59-5
• Molecular Formula: C6H14N2
• Molecular Weight: 114.191
• Hs Code.: 29213000
• European Community (EC) Number: 604-372-0
• UNII: R0ZN6K26EP
• DSSTox Substance ID: DTXSID501311027
• Nikkaji Number: J80.111I
• Wikidata: Q15605498
• Mol file: 1436-59-5.mol

Synonyms:1,2-cyclohexanediamine;1,2-cyclohexanediamine, (1R,2R)-;1,2-cyclohexanediamine, (1R-trans)-;1,2-cyclohexanediamine, (1S,2S)-;1,2-cyclohexanediamine, (1S-trans)-;1,2-cyclohexanediamine, (cis)-isomer;1,2-cyclohexanediamine, (trans)-(R)-isomer;1,2-cyclohexanediamine, (trans)-(S)-isomer;1,2-cyclohexanediamine, (trans)-isomer;1,2-DACH;1,2-diaminocyclohexane;1,2-diaminocyclohexane, (+)-;1,2-diaminocyclohexane, (-)-;1,2-diaminocyclohexane, cis-;1,2-diaminocyclohexane, trans-;cyclohexane-1,2-diamine;dach;meso-1,2-diaminocyclohexane;trans-1,2-cyclohexanediamine;trans-1,2-diaminocyclohexane

Chemical Property of cis-1,2-Diaminocyclohexane

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Melting Point: 8 °C
• Refractive Index: n20/D 1.493(lit.)
• Boiling Point: 193.643 °C at 760 mmHg
• PKA: 9.93(at 20℃)
• Flash Point: 75 °C
• PSA: 52.04000
• Density: 0.939 g/cm³
• LogP: 1.61560
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Completely miscible in water
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.115698455
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

99% ^*data from raw suppliers

cis-1,2-Diaminocyclohexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(C(C1)N)N
• Isomeric SMILES: C1CC[C@@H]([C@@H](C1)N)N
• Description: cis-1, 2-Diaminocyclohexane is a cyclohexane derivative. It can be used for the synthesis of platinum complexes with high antitumor activity. It can also be used for the preparation of multidentate ligands for uranyl and transition metal complexation. Moreover, it can also be used as the base for the manufacturing of titanium salalen catalyst. Its derivative also has the potential to be manufactured into a potent factor Xa inhibitor.
• Uses: cis-1,2-Diaminocyclohexane was used in the synthesis of platinum complexes that have high antitumor activity.It was also used in the synthesis of multidentate ligands for uranyl and transition metal complexation.

Technology Process of cis-1,2-Diaminocyclohexane

There total 39 articles about cis-1,2-Diaminocyclohexane 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: 100.0%

N-benzyl-N-(2-nitro-cyclohexyl)-hydroxylamine → trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(01)01746-4

Reference yield: 44.8%

trans-1,2-cyclohexandiol (1460-57-7) → 1,2,3,4,6,7,8,9-octahydrophenazine (4006-50-2) + 2-aminocyclohexanol (6850-38-0) + cis-cyclohexane-1,2-diamine (1436-59-5)

Guidance literature:

With dodecacarbonyl-triangulo-triruthenium; 4,5-bis((diisopropylphosphanyl)methyl)acridine; ammonia; In tert-Amyl alcohol; at 170 ℃; for 21h; Temperature; Inert atmosphere; Schlenk technique; Autoclave;

DOI:10.1002/cctc.201300407

Reference yield:

2-aminocyclohexanol (6850-38-0) → (1R,2R)-1,2-diaminocyclohexane (20439-47-8) + cis-cyclohexane-1,2-diamine (1436-59-5)

Guidance literature:

2-aminocyclohexanol; In ethanol; for 1h;

With ammonia; hydrogen; In ethanol; at 160 ℃; for 16h; under 3000.3 - 11251.1 Torr; Pressure; Reagent/catalyst; Solvent; Temperature; Overall yield = 98 %;

upstream raw materials:

(1R,2S)-cyclohexane-1,2-dicarboxylic acid

cis-cyclohexane-1,2-dicarboxylic acid dihydrazide

1,3-cyclohexanedionedioxime

diethyl (1RS,2SR)-cyclohexane-1,2-diylbiscarbamate

Downstream raw materials:

(1R,2R)-1,2-diaminocyclohexane

(S,S)-1,2-diaminocyclohexane

(+/-)-trans-N,N'-diisopropylcyclohexane-1,2-diamine

N-tert-butoxycarbonyl-N'-(trans-2-aminocyclohexyl)-p-nitrophenylalaninamide

Refernces

• 1、 -. "Preparation method of 1,2-cyclohexylenediamine". Paragraph 0024; 0025. . Retrieved 2017/01/02.
• 2、 Gao, Chuan-Zhu,Wang, Tian-Shuai,Chen, Jia,Fei, Fan,Zhang, Yan,Yang, Bo. "Efficient chiral resolution of (±)-cyclohexane-1,2-diamine". . p. 490 - 492. Retrieved 2014/11/08.