21436-03-3 Usage
Description
(1S,2S)-(+)-1,2-Diaminocyclohexane, also known as DACH, is a white to light yellow crystal powder with unique chemical properties. It is an optically active compound that plays a crucial role in various chemical reactions and applications due to its specific stereochemistry.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 21436-03-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,4,3 and 6 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 21436-03:
(7*2)+(6*1)+(5*4)+(4*3)+(3*6)+(2*0)+(1*3)=73
73 % 10 = 3
So 21436-03-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2
21436-03-3Relevant articles and documents
In vivo studies of a platinum(II) metallointercalator
Fisher, Dianne M.,Fenton, Ronald R.,Aldrich-Wright, Janice R.
, p. 5613 - 5615 (2008)
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
Glasovac, Zoran,Kirin, Sre?ko I.,Kokan, Zoran,Opa?ak, Sa?a,Peri?, Berislav
, p. 2115 - 2128 (2019/01/04)
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
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Paragraph 0013; 0014; 0015, (2017/08/29)
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.
