108-13-4 Usage
Description
Malonamide is a dicarboxylic acid diamide that is malonic acid in which both carboxy groups have been replaced by carbamoyl groups. It is functionally related to a malonic acid and is characterized by its white crystalline powder appearance. Malonamide derivatives are obtained through a one-pot, five-component condensation reaction of isocyanide, Meldrum's acid, arylidene malononitrile, and two amine molecules in CH2Cl2.
Uses
1. Used in Chemical Synthesis:
Malonamide is used as a key intermediate in the synthesis of malonamic acid, malonamate, and various malonamide derivatives of heterocyclic compounds with anti-inflammatory activity. Its unique structure allows for the creation of a wide range of compounds with potential pharmaceutical applications.
2. Used in Analytical Chemistry:
Malonamide serves as a reagent for the fluorimetric determination of reducing carbohydrates. This application takes advantage of its ability to react with reducing sugars, providing a quantitative measurement that can be useful in various research and quality control settings.
3. Used in Rare Earth Element Extraction:
The malonamide-based ionic liquid extractant is employed in the extraction of europium(III) and other trivalent rare earth elements from a nitric acid medium. This application highlights the utility of malonamide in the field of materials science and engineering, particularly in the recovery and purification of valuable elements.
4. Used in Pharmaceutical Research:
Malonamide and its derivatives hold potential in the development of new anti-inflammatory drugs. The synthesis of heterocyclic compounds with anti-inflammatory properties using malonamide as a starting material can lead to the discovery of novel therapeutic agents for the treatment of various inflammatory conditions.
Hazard
Mildly toxic by ingestion.
Synthesis
The synthesis of?Malonamide is as follows:A typical reaction was carried out in a 10 mL flask. Benzonitrile (2 mmol), CuII-4 ? (0.2 g), acetaldoxime (6 mmol) and MeOH (4 mL) were stirred at 65 °C for 4 h. The solid was filtered, washed with MeOH and the filtrate evaporated. The residue was subjected to GC-MS analysis and NMR spectroscopy. The filtered catalyst can be recycled after drying at about 150 °C for 1 h.
Purification Methods
Crystallise the amide from water. [Beilstein 2 IV 1887.]
Check Digit Verification of cas no
The CAS Registry Mumber 108-13-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 108-13:
(5*1)+(4*0)+(3*8)+(2*1)+(1*3)=34
34 % 10 = 4
So 108-13-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H6N2O2/c4-2(6)1-3(5)7/h1H2,(H2,4,6)(H2,5,7)
108-13-4Relevant articles and documents
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Lemons et al.
, p. 467 (1942)
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Transfer Hydration of Dinitriles to Dicarboxamides
Naka, Hiroshi,Naraoka, Asuka
, p. 1977 - 1980 (2019)
We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1, n -dinitriles (n = 1-6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.
Corresponding amine nitrile and method of manufacturing thereof (by machine translation)
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Paragraph 0124; 0125; 0126; 0127, (2018/07/15)
The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.
Modulation of Nitrile Hydratase Regioselectivity towards Dinitriles by Tailoring the Substrate Binding Pocket Residues
Cheng, Zhongyi,Cui, Wenjing,Xia, Yuanyuan,Peplowski, Lukasz,Kobayashi, Michihiko,Zhou, Zhemin
, p. 449 - 458 (2017/12/15)
The regioselective hydration of dinitriles is one of the most attractive approaches to prepare ω-cyanocarboxamides or diamides and such regioselectivity is often beyond the capability of chemical catalysts. The use of nitrile hydratase to biotransform dinitriles selectively would be highly desirable. Molecular docking of two aliphatic dinitriles and two aromatic dinitriles into the active site of a nitrile hydratase (NHase) from Rhodococcus rhodochrous J1 allowed the identification of proximal NHase substrate binding pocket residues. Four residues (βLeu48, βPhe51, βTyr68, and βTrp72) were selected for single- and double-point mutations to modulate the NHase regioselectivity towards dinitriles. Several NHase mutants with an altered regioselectivity were obtained, and the best one was Y68T/W72Y. Docking experiments further indicated that the poor binding affinity of aliphatic and aromatic ω-cyanocarboxamides to the NHase variants resulted in distinct regioselectivity between wild-type and mutated NHases.