1121-22-8 Usage
Description
(+/-)-trans-1,2-Diaminocyclohexane, also known as DACH, is an organic compound with the chemical formula C6H14N2. It is a clear colorless to light yellow liquid that plays a crucial role in various chemical reactions and applications due to its unique structure and properties.
Uses
Used in Chemical Synthesis:
(+/-)-trans-1,2-Diaminocyclohexane is used as a key component in the synthesis of macrocyclic [3+3] hexa Schiff bases. These compounds have a wide range of applications in various fields, including pharmaceuticals, materials science, and catalysis.
Used in Chiral Ligands and Auxiliaries:
(+/-)-trans-1,2-Diaminocyclohexane is employed as a chiral ligand in asymmetric catalysis, which is an essential process in the synthesis of enantiomerically pure compounds. These compounds are crucial in the pharmaceutical industry, as they often exhibit different biological activities and are required for the development of many drugs.
Used in Chiral Stationary Phases:
(+/-)-trans-1,2-Diaminocyclohexane is also used in the preparation of chiral stationary phases, which are essential in the separation and analysis of enantiomers. This application is particularly relevant in the pharmaceutical and agrochemical industries, where the purity and stereochemistry of compounds are critical.
Used in Multidentate Ligand Preparation:
(+/-)-trans-1,2-Diaminocyclohexane is utilized in the synthesis of multidentate ligands, which are complex molecules that can bind to a central metal ion through multiple donor atoms. These ligands are vital in various fields, including catalysis, supramolecular chemistry, and materials science.
Used in [2+2] Macrocyclization:
(+/-)-trans-1,2-Diaminocyclohexane is used to prepare [2+2] macrocyclization products by reacting with aliphatic dialdehydes. Macrocyclic compounds have unique properties and are used in various applications, such as molecular recognition, drug delivery, and catalysis.
Purification Methods
Purify and store the diamine as for the cis-isomer above as it is a strong base and becomes yellow on storage. [Beilstein 13 IV 1.]
Check Digit Verification of cas no
The CAS Registry Mumber 1121-22-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 1 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1121-22:
(6*1)+(5*1)+(4*2)+(3*1)+(2*2)+(1*2)=28
28 % 10 = 8
So 1121-22-8 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-/m0/s1
1121-22-8Relevant articles and documents
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Hewgill,Jefferies
, p. 805,807 (1956)
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Method for synthesizing trans-cyclohexyldiamine
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, (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.
A diamine-exchange reaction of dihydropyrazines
Yamaguchi, Tadatoshi,Ito, Shigeru,Iwase, Yukiko,Watanabe, Kenji,Harano, Kazunobu
, p. 1677 - 1680 (2007/10/03)
Dihydropyrazines reacted with 1,2-diamines to form tetraazadecalins as intermediates, and then the reaction proceeded forward to dissociate into alternate dihydropyrazine and diamine, or backward to dissociate into the starting materials in certain equilibrium. The product distribution is controlled by diamine-exchange equilibrium reaction. The various equilibrium reactions were analyzed by NMR spectroscopy.
Diastereo- and enantioselective synthesis of vicinal diamines via aza-Michael addition to nitroalkenes
Enders, Dieter,Wiedemann, Juergen
, p. 1443 - 1450 (2007/10/03)
The asymmetric synthesis of protected 1,2-diamines 4 by aza-analogous Michael addition of (-)-(2S,3R,4R,5S)-1-amino-3,4-dimethoxy-2,5-bis(methoxymethyl)pyrrolid ine (ADMP) to nitroalkenes 1 in good overall yields and high enantiomeric excesses (ee = 93-96%) is described. The auxiliary constitutes a novel chiral equivalent of ammonia and is removed under reductive N-N bond cleavage with Raney nickel, which also reduces the nitro group. The absolute configuration was determined by NMR-spectroscopic methods and polarimetry.
