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

Base Information

• Chemical Name: (1R,2R)-(-)-1,2-Diaminocyclohexane
• CAS No.: 20439-47-8
• 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: 20439-47-8.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: white to light yellow crystal powder
• Vapor Pressure: 2.031mmHg at 25°C
• Melting Point: 41-45 °C
• Refractive Index: -25.5 ° (C=5, 1mol/L HCl)
• Boiling Point: 193.6 °C at 760 mmHg
• PKA: 10.76±0.70(Predicted)
• Flash Point: 75 °C
• PSA: 52.04000
• Density: 0.939 g/cm³
• LogP: 1.61560
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble 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

(1R,2R)-(-)-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: (1R,2R)-(-)-1,2-Diaminocyclohexane can be used as a building block for chiral ligands. suzuki reaction (1R,2R)-(-)-1,2-Diaminocyclohexane is a versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

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

There total 62 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: 98.0%

(1R,2R)-1,2-diaminocyclohexane tartrate (32044-22-7,39961-95-0) → (1R,2R)-1,2-diaminocyclohexane (20439-47-8)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1016/j.tetasy.2010.03.001

Reference yield: 97.0%

trans-2-azido-N,N-dibenzylcyclohexan-1-amine → (1R,2R)-1,2-diaminocyclohexane (20439-47-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 60h; under 1034.32 Torr;

DOI:10.1016/j.tetlet.2014.12.101

Reference yield: 95.0%

((1R,2R)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine (329321-24-6) → (1R,2R)-1,2-diaminocyclohexane (20439-47-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 48h; under 2068.59 Torr;

DOI:10.1016/S0040-4039(00)01793-7

upstream raw materials:

trans-1,2-Diaminocyclohexane

rac-diaminocyclohexane

malonic acid dimethyl ester

((1R,2R)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine

Downstream raw materials:

(R,R)-N,N'-bis(salicylidene)-1,2-cyclohexanediamine

C₁₈H₂₀N₄O₂

(R,R)-(+)-trans-4,5-tetramethyleneimidazolidine-2-thione

(1R,2R)-N,N'-bis(2,4,6-trimethylbenzenesulfonyl)-cyclohexane-1,2-diamine

Refernces

Bowl-shaped C(3)-symmetric receptor with concave phosphine oxide with a remarkable selectivity for asparagine derivatives.

10.1021/ol034168b

The research focuses on the development of a bowl-shaped C3-symmetric receptor (1a) with a concave phosphine oxide functionality within its molecular bowl, designed to exhibit remarkable selectivity for asparagine (Asn) derivatives. The purpose of this study was to construct a host molecule with a rigidly defined cavity that could mimic the active site of enzymes, thereby functioning as a reaction or binding site with unique properties. The researchers synthesized 1a and 1b, starting with the trialkylation of tris(chloromethyl)phosphine oxide with dimethyl 5-mercaptoisophthalate, followed by an intermolecular macrolactamization process. The conclusions drawn from the study indicate that 1a showed a high residue selectivity for Asn alkyl amide against other amino acid derivatives like Gln, Glu, and Asp, which have similar H-bond donor/acceptor geometries. This selectivity was attributed to the cooperative hydrogen bonding between the phosphine oxide in the cavity of 1a and the guest molecules, along with subtle differences in the intermolecular hydrogen bonding mode within the cavity. The chemicals used in the synthesis process included tris(chloromethyl)phosphine oxide, dimethyl 5-mercaptoisophthalate, and (1R,2R)-diaminocyclohexane, among others.