Malonamide

Base Information

• Chemical Name: Malonamide
• CAS No.: 108-13-4
• Molecular Formula: C3H6N2O2
• Molecular Weight: 102.093
• Hs Code.: 29241900
• European Community (EC) Number: 203-553-8
• NSC Number: 2134
• UNII: QVQ8CNG255
• DSSTox Substance ID: DTXSID1040116
• Nikkaji Number: J2.415E
• Wikidata: Q27287520
• Mol file: 108-13-4.mol

Synonyms:malonamide;malonic acid diamide;malonic diimidate

Chemical Property of Malonamide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.13E-08mmHg at 25°C
• Melting Point: 172-175 °C(lit.)
• Refractive Index: 1.491
• Boiling Point: 460.9 °C at 760 mmHg
• PKA: 7.00±0.70(Predicted)
• Flash Point: 232.5 °C
• PSA: 86.18000
• Density: 1.281 g/cm³
• LogP: -0.25230
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in HCl.
• Water Solubility.: 180 g/L (20 ºC)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 102.042927438
• Heavy Atom Count: 7
• Complexity: 87.1

Purity/Quality:

99% ^*data from raw suppliers

Malonamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Amides, Other
• Canonical SMILES: C(C(=O)N)C(=O)N
• Description: Malonamide is a dicarboxylic acid diamide that is malonic acid in which both carboxy groups have been replaced by carbamoyl groups.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.
• Uses: Malonamide is used in the synthesis of malonamic acid, malonamate and malonamide derivative of some heterocyclic compounds with antiinflammatory activity. Malonamide is a reagent for fluorimetric determination of reducing carbohydrates. The malonamide-based ionic liquid extractant was used in the extraction of europium(iii) and other trivalent rare earth elements from nitric acid medium. The malonamide-based ionic liquid extractant was used in the extraction of europium(iii) and other trivalent rare-earth ions from nitric acid medium.

Technology Process of Malonamide

There total 43 articles about Malonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

malononitrile (109-77-3) → malonodiamide (108-13-4)

Guidance literature:

With Acetaldehyde oxime; In methanol; at 65 ℃; for 4h;

DOI:10.1016/j.tetlet.2011.09.012

Reference yield: 91.0%

cyanoacetic acid amide (107-91-5) → malonodiamide (108-13-4)

Guidance literature:

With sodium hydroxide;

DOI:10.1080/00397911.2014.987352

Reference yield:

1,3-Dihydro-3-oxo-2-isobenzofuranylidenmalonsaeurediethylester (897-38-1) + ammonia (7664-41-7) → malonodiamide (108-13-4) + phthalamide (88-96-0)

Guidance literature:

upstream raw materials:

carbon suboxide

ethyl malonamate

methanetricarboxylic acid triethyl ester

methanetetracarboxylic acid tetraethyl ester

Downstream raw materials:

2-hydroxy-4,6-dimethyl-nicotinic acid amide

BARBITURIC ACID

4-methyl-2-(2-oxo-2H-1-benzopyran-3-yl)<1>benzopyrano<3,4-c>pyridin-5-one

1-benzyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-isoquinoline-4-carboxylic acid amide

Refernces

Enantioselective synthesis of C₂-symmetric spirobilactams via Pd-catalyzed intramolecular double N-arylation

10.1021/ol900016g

The study presents an enantioselective synthesis method for C2-symmetric spirobilactams, which are important in synthetic chemistry due to their rigid spiro backbone that creates an effective asymmetric environment. The researchers used a Pd/BINAP complex as a catalyst to achieve an intramolecular double N-arylation of malonamides bearing 2-bromoarylmethyl groups, resulting in C2-symmetric spirobi(3,4-dihydro-2-quinolone) derivatives with up to 70% enantiomeric excess (ee). Key chemicals involved in the study include malonamides, bromoarenes, Pd(OAc)2 as the palladium source, (S)-BINAP as the chiral ligand, and various bases and solvents such as Cs2CO3, K3PO4, and DMPU. These chemicals served the purpose of facilitating the catalytic asymmetric synthesis, which is a highly practical method for preparing optically active spiranes, potentially useful as ligands and organocatalysts.

Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[ b][1,4]oxazepine and malonamide derivatives

10.1021/cc100032d

The study presents a novel one-pot multicomponent reaction for the synthesis of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives. The reaction involves 2-aminophenols, Meldrum’s acid, and isocyanides, and it proceeds at ambient temperature with good to excellent yields. These chemicals serve to create a new class of substituted malonamide and tetrahydrobenzo[b][1,4]oxazepine derivatives, which are significant in medicinal chemistry due to their potential as ionophores for selective electrodes, liquid-liquid extractants for nuclear waste management, and pharmaceutical compounds with diverse biological activities, including anticancer properties.