(1R,2R)-(-)-1,2-Diaminocyclohexane

Base Information

• Chemical Name: (1R,2R)-(-)-1,2-Diaminocyclohexane
• CAS No.: 1121-22-8
• Deprecated CAS: 41013-43-8,1881285-37-5
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.191
• Hs Code.: 29213000
• European Community (EC) Number: 601-163-6,606-556-6
• UNII: 37EKL250EE,88RM10ID0P
• DSSTox Substance ID: DTXSID60883654
• Nikkaji Number: J82.963C
• Wikipedia: Trans-1,2-Diaminocyclohexane
• Wikidata: Q15605490,Q72462761
• Mol file: 1121-22-8.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 (1R,2R)-(-)-1,2-Diaminocyclohexane

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Melting Point: 14-15 °C(lit.)
• Refractive Index: n20/D 1.489(lit.)
• Boiling Point: 193.643 °C at 760 mmHg
• PKA: 9.94(at 20℃)
• Flash Point: 75 °C
• PSA: 52.04000
• Density: 0.939 g/cm³
• LogP: 1.61560
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble
• 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:

(±)-trans-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

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Cyclic
• Canonical SMILES: C1CCC(C(C1)N)N
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)N)N
• Uses: (^+)-trans-1,2-Diaminocyclohexane is employed in the synthesis of macrocyclic [3+3] hexa Schiff base. It also plays an important role in the preparation of multidentate ligands, chiral auxiliaries and chiral stationary phases. Further, it is used to prepare [2+2] macrocyclization by reacting with aliphatic dialdehydes. In addition to this, it acts as a chiral ligand, which finds application in asymmetric catalysis. (±)-trans-1,2-Diaminocyclohexane was used in the synthesis of macrocyclic [3+3] hexa Schiff base. It was also employed in the synthesis of multidentate ligands, chiral auxiliaries and chiral stationary phases.

Technology Process of (1R,2R)-(-)-1,2-Diaminocyclohexane

There total 33 articles about (1R,2R)-(-)-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: 47.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + trans-1,2-Diaminocyclohexane (1121-22-8,1436-59-5,20439-47-8,21436-03-3,41013-43-8,694-83-7) → trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine (1121-22-8,38383-49-2,43148-65-8,46026-77-1,53100-04-2,53152-68-4,53152-69-5)

Guidance literature:

With formic acid; In water; at 0 - 80 ℃;

DOI:10.1021/ja970029b

Reference yield: 38.0%

N,N,N',N'-Tetramethyl-cyclohexane-1,2-diamine; compound with GENERIC INORGANIC NEUTRAL COMPONENT → trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine (1121-22-8,38383-49-2,43148-65-8,46026-77-1,53100-04-2,53152-68-4,53152-69-5)

Guidance literature:

With sodium hydride; In benzene;

upstream raw materials:

7-azabicyclo[4.1.0]heptane

1,2-cyclohexanedionedioxime

1,3-cyclohexanedionedioxime

trans-1,2-dinitrocyclohexane

Downstream raw materials:

trans-1,2-Cyclohexanediaminetetraacetic acid

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

trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine

(rac)-trans-4,5-tetramethyleneimidazolidin-2-one

Refernces

• 1、 Jaeger,Bijkerk. "-". . p. 97,98. Retrieved 1937.
• 2、 O'Neil, Ian A.,Cleator, Ed,Southern, J. Mike,Bickley, Jamie F.,Tapolczay, David J.. "The stereospecific addition of hydroxylamines to α,β-unsaturated sulfones, nitriles and nitro compounds". . p. 8251 - 8254. Retrieved 2007/10/03.
• 3、 Remenar, Julius F.,Lucht, Brett L.,Collum, David B.. "Lithium diisopropylamide solvated by monodentate and bidentate ligands: Solution structures and ligand binding constants". . p. 5567 - 5572. Retrieved 2007/10/03.