1436-59-5 Usage
Description
cis-1,2-Diaminocyclohexane is a cyclohexane derivative characterized by its clear colorless liquid appearance. It is known for its ability to perturb the spectrum of free pyrroloquinoline quinone (PQQ) and induce similar changes in the spectrum of lysyl oxidase. This versatile compound is utilized in various applications, including the synthesis of platinum complexes with high antitumor activity, the preparation of multidentate ligands for uranyl and transition metal complexation, and as a base for the manufacturing of titanium salalen catalysts. Additionally, its derivatives have the potential to be developed into potent factor Xa inhibitors.
Uses
Used in Pharmaceutical Industry:
cis-1,2-Diaminocyclohexane is used as a key component in the synthesis of platinum complexes, which are known for their high antitumor activity. This application is significant in the development of novel cancer treatments, as these platinum complexes can target and inhibit the growth of cancer cells effectively.
Used in Chemical Industry:
cis-1,2-Diaminocyclohexane serves as a crucial raw material in the preparation of multidentate ligands for uranyl and transition metal complexation. These ligands are essential in various chemical processes and reactions, particularly in the field of inorganic chemistry, where they play a vital role in stabilizing and characterizing metal complexes.
Used in Catalyst Manufacturing:
As a base for the manufacturing of titanium salalen catalysts, cis-1,2-diaminocyclohexane contributes to the development of efficient and selective catalysts for various industrial applications, including the production of polymers and the synthesis of fine chemicals.
Used in the Development of Factor Xa Inhibitors:
The derivatives of cis-1,2-diaminocyclohexane have the potential to be manufactured into potent factor Xa inhibitors, which are important in the treatment of various thrombotic disorders and conditions related to blood clotting. This application highlights the compound's versatility and its potential impact on the medical field.
References
Khokhar, Abdul R., et al. "Chemical and Biological Studies on a Series of Novel (trans-(1R,2R)-, trans-(1S,2S)-, and cis-1,2-Diaminocyclohexane)platinum(IV) Carboxylate Complexes." Journal of Medicinal Chemistry 40.1(1997):112.
Mauldin, S. K., et al. "High-performance liquid chromatographic separation of platinum complexes containing the cis-1,2-diaminocyclohexane carrier ligand. " Analytical Biochemistry157.1 (1986):129-43.
Berkessel, A, et al. "Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: enantioselective epoxidation of terminal non-conjugated olefins with H2O2. " Angewandte Chemie 52.32(2013):8467-71.
Yoshikawa, K, et al. "Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: exploration of 5-6 fused rings as alternative S1 moieties. " Bioorganic & Medicinal Chemistry 17.24(2009):8221.
http://www.sigmaaldrich.com/catalog/product/aldrich/307467?lang=en®ion=US
Purification Methods
Dry the diamine over solid KOH and distil it in a vacuum. It is a strong base, keep away from CO2, store in the dark under N2. [Beilstein 13 IV 1.]
Check Digit Verification of cas no
The CAS Registry Mumber 1436-59-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,3 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1436-59:
(6*1)+(5*4)+(4*3)+(3*6)+(2*5)+(1*9)=75
75 % 10 = 5
So 1436-59-5 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/t5-,6+
1436-59-5Relevant articles and documents
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.
CYCLOHEXANEDIAMINE COMPOUNDS AND METHODS FOR THEIR PREPARATION
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Paragraph 0099, (2014/10/04)
The present invention provides processes for the preparation of cyclohexanediamine compounds of formula Ia and intermediates thereof. The compounds are useful as Syk kinase inhibitors and in various pharmaceutical compositions, and particularly useful for treating conditions mediated at least in part by Syk kinase activity.
Direct amination of bio-alcohols using ammonia
Pingen, Dennis,Diebolt, Olivier,Vogt, Dieter
, p. 2905 - 2912 (2013/10/21)
A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.