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

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

Uses

1. Used in Suzuki Reaction:
(1S,2S)-(+)-1,2-Diaminocyclohexane is used as a versatile ligand in the Suzuki reaction for the formation of metal complexes. Its application in this reaction is due to its ability to facilitate the formation of carbon-carbon bonds, which are essential in the synthesis of various organic compounds.
2. Used for Synthesis of Optically Active Products:
(1S,2S)-(+)-1,2-Diaminocyclohexane is used as a key intermediate in the synthesis of optically active products. Its optical activity allows for the creation of chiral molecules, which are important in the pharmaceutical industry for developing drugs with specific biological activities.
3. Used in the Synthesis of Chiral Tropocoronands:
(1S,2S)-(+)-1,2-Diaminocyclohexane is used as a versatile ligand for the formation of metal complexes, which are then used in the synthesis of chiral tropocoronands. These chiral tropocoronands have potential utility in asymmetric catalysis, a field that is vital for the development of enantiomerically pure compounds.
4. Used in Pharmaceutical Industry:
(1S,2S)-(+)-1,2-Diaminocyclohexane is used as a building block for the synthesis of various pharmaceutical compounds. Its unique stereochemistry allows for the creation of chiral drugs with specific therapeutic effects.
5. Used in Chemical Research:
(1S,2S)-(+)-1,2-Diaminocyclohexane is used as a research compound in the development of new chemical methods and techniques. Its optical activity and unique properties make it an interesting subject for study in various fields of chemistry.

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

• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 694-83-7 rac-diaminocyclohexane 
• 108-59-8 malonic acid dimethyl ester 
• 329321-25-7 ((1S,2S)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine 
• 492-99-9 1,2-cyclohexanedionedioxime 
• 87-69-4 L-Tartaric acid 
• 32044-22-7 (R,R)-1,2-diammoniumcyclohexane mono-(+)-tartrate salt 
• 32044-22-7 (1S,2S)-1,2-diaminocyclohexane D-tartrate 
• 2802-07-5 1,3-cyclohexanedionedioxime 
• 108-45-2 m-phenylenediamine 
• 286-20-4 cyclohexane-1,2-epoxide 
• 329321-22-4 2-((R)-1-Phenyl-ethylamino)-cyclohexanol 
• 329321-23-5 7-((R)-1-Phenyl-ethyl)-7-aza-bicyclo[4.1.0]heptane 
• 286-18-0 7-azabicyclo<4.1.0>heptane 

Downstream Products

• 148410-63-3 C₃₀H₄₄N₄⁽²⁺⁾*2Cl^(1-) 
• 184866-89-5 Acetic acid 4-((E)-2-{(1S,2S)-2-[(E)-3-(4-acetoxy-phenyl)-acryloylamino]-cyclohexylcarbamoyl}-vinyl)-phenyl ester 
• 424829-08-3 N,N'-bis(2,2'-bipyridyl-5-yl)carbonyl-(1S,2S)-(+)-1,2-diaminocyclohexane 
• 479498-77-6 (1S,2S)-N,N'-bis(2-nitrophenyl)cyclohexane-1,2-diamine 
• 874662-45-0 1-((1S,2S)-2-Amino-cyclohexyl)-3-((S)-1,2,2-trimethyl-propyl)-thiourea 

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.

Thermochemical and Structural Studies of New Chiral and Achiral Long Alkyl Chain Functionalized Imidazolinium Ionic Liquids

Adding to the versatile class of ionic liquids (ILs), an entirely new series of imidazolinium-based ionic liquids is reported herein, offering chirality and important thermal characteristics, such as polymorphism, glass transition, and plastic crystalline behavior. An efficient and general procedure for the preparation of long N,N′-alkyl chain-substituted compounds with either saturated (s) or chiral (c) cyclohexyl (cyC6)-substituted imidazolium (Im) backbones, namely, [C12C12RsIm][A] (A = Br-, [BF4]-, [ClO4]-, [PF6]- R = H, Me, iPr) and [C12C12cIm-cyC6][A] (A = Br-, I-, [I3]-, [BF4]-, [ClO4]-, [PF6]-, [SbF6]-, [BPh4]-), was developed, and the novel compounds were studied by thermochemical methods (DSC, TGA), X-ray diffraction in the small angle regime (SAXS), single-crystal X-ray diffraction (SC-XRD), and specific rotation analysis.

“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.

Method for synthesizing trans-cyclohexyldiamine

The invention discloses a method for synthesizing trans-cyclohexyldiamine. The method comprises the following steps: by using epoxy cyclohexane as the raw material, carrying out ring opening with ammonia water, adding sulfuric acid for dewatering and salification, adding free alkali, carrying out ring opening with ammonia water, and distilling to obtain the trans-cyclohexyldiamine. The method has the advantages of high repetitiveness of the synthesis route, and simple and accessible raw materials, and provides an alternative scheme for obtaining the trans-cyclohexyldiamine pure product.

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.

METHOD OF PRODUCING OPTICALLY ACTIVE TRANS-1,2-DIAMINOCYCLOHEXANE

A method produces optically active trans-1,2-diaminocyclohexane, in which a crystal of optically active trans-1,2-diaminocyclohexane is obtained by crystallization from a solution of optically active trans-1,2-diaminocyclohexane. Optically active trans-1,2-diaminocyclohexane with high purity is obtained in a favorable yield from a solution of optically active trans-1,2-diaminocyclohexane. The optically active trans-1,2-diaminocyclohexane with high purity is useful as a raw material for a large number of medicines.

Preparation of C 2-Symmetric Biaryl Bisiminium Salts and Their Use as Organocatalysts for Asymmetric Epoxidation

Two C 2-symmetric bisiminium salt species containing biphenylazepinium units and derived from two chiral diamines were prepared and tested as organocatalysts for asymmetric epoxidation.

The iron(II) complex [Fe(CF3SO3)2(mcp)] as a convenient, readily available catalyst for the selective oxidation of methylenic sites in alkanes

The efficient and selective oxidation of secondary C-H sites of alkanes is achieved by using low catalyst loadings of a non-expensive, readily available iron catalyst [Fe(II)(CF3SO3)2(mcp)], {Fe-mcp, [mcp=N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)cyclohexane-trans-1,2-diamine]}, and hydrogen peroxide (H2O2) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated in synthetically amenable yields. The easy access to large quantities of the catalyst and the simplicity of the C-H oxidation procedure make this system a particularly convenient tool to carry out alkane C-H oxidation reactions on the preparative scale, and in short reaction times.

Efficient chiral resolution of (±)-cyclohexane-1,2-diamine

A novel and efficient method has been developed for the chiral resolution and separation from cis-cyclohexane-1,2-diamine of (±)-cyclohexane-1,2- diamine, which reacts with xylaric acid, a substitute for tartaric acid. This method provides (1R,2R)-cyclohexane-1,2-diamine, and (1S,2S)-cyclohexane-1,2- diamine and cis-cyclohexane-1,2-diamine in good yield with high optical purity.

Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.