21436-03-3

Basic information

• Product Name: (1S,2S)-(+)-1,2-Diaminocyclohexane
• Synonyms: S-DACH;(+)-(S,S)-1,2-DIAMINOCYCLOHEXANE;(S,S)-(+)-1,2-DIAMINOCYCLOHEXANE;(S,S)-1,2-DIAMINOCYCLOHEXANE;SS-DAC;(+)-(S,S)-DACH;(S,S)-DACH;SS-DIAMINOCYCLOHEXANE
• CAS NO: 21436-03-3
• Molecular Formula: C6H14N2
• Molecular Weight: 114.19
• Product Categories: chiral;API intermediates;Chiral reagent;Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Compound;organic amine;Chiral Nitrogen;DACH&Trost Series
• Mol File: 21436-03-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: 40-43 °C(lit.)
• Boiling Point: 104-110 °C40 mm Hg(lit.)
• Flash Point: 169 °F
• Appearance: White to light beige/Crystals or Powder
• Density: 0.951
• Refractive Index: 1.4886
• Storage Temp.: 2-8°C
• PKA: 10.76±0.70(Predicted)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• BRN: 2801645
• CAS DataBase Reference: (1S,2S)-(+)-1,2-Diaminocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-1,2-Diaminocyclohexane(21436-03-3)
• EPA Substance Registry System: (1S,2S)-(+)-1,2-Diaminocyclohexane(21436-03-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 3
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 21436-03-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 21436-03-3 differently. You can refer to the following data:
1. suzuki reaction
2. For synthesis of optically active products
3. Versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

Purification Methods

Distil or recrystallise the diamine from pet ether under N2 or Ar. Store it as above. The 1S,2S-base D-tartrate salt has M 264.3, m 180 -1 8 4o(dec) and [] 25 -12.5o (c 4, H2O) from which the free base can be purified or optically enriched. It is a useful chiral synthon. [Fjii et al. J Chem Soc, Chem Commun 45 1985, Takahashi et al. Tetrahedron Lett 30 7095 1989, Hanassian et al. J Org Chem 58 1991 1993, Beilstein 13 III 7.]

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

Upstream product

• 87-69-4 L-Tartaric acid 
• 694-83-7 rac-diaminocyclohexane 
• 329321-25-7 ((1S,2S)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 108-59-8 malonic acid dimethyl ester 
• 286-20-4 cyclohexane-1,2-epoxide 
• 286-18-0 7-azabicyclo<4.1.0>heptane 
• 110-83-8 cyclohexene 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 108-45-2 m-phenylenediamine 
• 71172-32-2 trans-1,2-dinitrocyclohexane 
• 2802-07-5 1,3-cyclohexanedionedioxime 
• 492-99-9 1,2-cyclohexanedionedioxime 
• 286-18-0 7-azabicyclo[4.1.0]heptane 

Downstream Products

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 109669-64-9 C₂₀H₁₈Cl₄N₂O₄ 
• 186144-56-9 N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester 
• 219143-76-7 (3aS,7aS)-2-(3,4-Dimethoxy-benzyl)-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole 
• 57707-55-8 trans-1,2-diphenylamidocyclohexane 
• 308798-01-8 (R,R)-N,N'-(Cyclohexane-1,2-diyl)bis(methyl 4-carbamoyl-3-oxabutanoate) 
• 180683-64-1 tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate 

Relevant articles and documents

In vivo studies of a platinum(II) metallointercalator

An in vivo study for determining the toxicity and efficacy of [Pt(S,S-dach)(phen)Cl2·1.5H2O·0.5HCl (PHENSS) in female Specific Pathogen Free (SPF) Swiss nude mice bearing PC3 tumour xenografts revealed PHENSS to be non-toxic and effective in decreasing tumour growth. The Royal Society of Chemistry.

“Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.

Using enantioselective dispersive liquid–liquid microextraction for the microseparation of trans-cyclohexane-1,2-diamine enantiomers

A new chiral separation system effective for the enantioselective extraction of racemic trans-cyclohexane-1,2-diamine is presented. Enantioselective dispersive liquid–liquid microextraction has been used for the chiral microseparation of trans-cyclohexane-1,2-diamine, with a chiral azophenolic crown ether being identified as a versatile chiral selector. The influence of various process conditions on the extraction performance was studied experimentally. It was found that the operational selectivity in one extraction step is mainly related to the type and volume of the solvents, chiral selector concentration, extraction time, temperature of sample solution, and pH. At optimum conditions (300?μL of diethyl ether as the extraction solvent 1?mL of methanol as the disperser solvent, with 5?mmol?L?1 chiral selector concentration, pH of the sample equal to 4.5, 30?min extraction time and a temperature of 10?°C), the distribution ratio of (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine was 18.3 and 1.8, respectively, while the enantioselectivity value of 10.2 was found at the optimum condition.