26391-06-0

Basic information

• Product Name: 2-Cyano-N,N-diethylacetamide
• Synonyms: N,N-DIETHYLCYANOACETAMIDE;2-Cyano-N,N-diethylacetamide;2-Cyano-N,N-diethylacetaMid;N,N-diethyl caynoacetaMide;N,N-Diethyl-2-cyanoacetoamide;2-Cyano-N,N-diethylacetamide
• CAS NO: 26391-06-0
• Molecular Formula: C₇H₁₂N₂O
• Molecular Weight: 140.18
• Product Categories: pharmaceutical intermediates;Aliphatics;Miscellaneous Reagents
• Mol File: 26391-06-0.mol

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 114°C/4mmHg(lit.)
• Flash Point: >110℃
• Appearance: Yellow to brown liquid
• Density: 1.013 g/mL at 25 °C
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: n20/D1.466
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform, Ethyl Acetate, Tetrahydrofuran, Methanol
• PKA: 4.53±0.10(Predicted)
• CAS DataBase Reference: 2-Cyano-N,N-diethylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyano-N,N-diethylacetamide(26391-06-0)
• EPA Substance Registry System: 2-Cyano-N,N-diethylacetamide(26391-06-0)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 26391-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Cyano-N,N-diethylacetamide is used as an intermediate in the synthesis of N,N-diethyl 2-cyano-2-fluoro-2-phenylthioacetoamide, which is further utilized in the production of various cyanofluoroamides. These cyanofluoroamides have potential applications in the pharmaceutical industry, particularly in the development of new drugs.
Used in Entacapone Production:
In the pharmaceutical industry, 2-Cyano-N,N-diethylacetamide is also used in the synthesis of entacapone, a catechol-O-methyltransferase inhibitor. Entacapone is an essential drug used in the treatment of Parkinson's disease, and its production involves reacting 2-Cyano-N,N-diethylacetamide with 3,4-dihydroxy-5-nitrobenzaldehyde.
Used in Fluorophore Synthesis:
2-Cyano-N,N-diethylacetamide serves as a building block in the synthesis of fluorophores, which are essential for various applications in the field of biochemistry and molecular biology. Specifically, it is used in the development of endoplasmic reticulum probes, which are crucial for studying the structure and function of the endoplasmic reticulum in cells.

InChI:InChI=1/C7H12N2O/c1-3-9(4-2)7(10)5-6-8/h3-5H2,1-2H3

Upstream product

• 26391-04-8 diethylamino-propynenitrile 
• 109-89-7 diethylamine 
• 105-56-6 ethyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 16130-58-8 cyanoacetic acid chloride 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 28112-20-1 1-Diaethylamino-1-methoxy-2-cyanaethylen 
• 126832-95-9 2-Cyano-5-isopropylsulfanyl-[1,3]dithiane-2-carboxylic acid diethylamide 
• 7119-92-8 diethyl-N-nitroamine 
• 698351-77-8 2-cyano-N,N-diethyl-2-fluoro-acetamide 
• 698351-25-6 N,N-diethyl 2-cyano-2-fluoro-2-phenylthioacetoamide 
• 158693-04-0 (Z)-N,N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-acrylamide 
• 857629-78-8 (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide 
• 130929-57-6 entacapone 
• 145195-63-7 (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide 
• 857629-79-9 (E)-N,N-diethyl-2-cyano-3-(3-ethoxy-4-hydroxy-5-nitrophenyl)acrylamide 

Relevant articles and documents

Synthesis and Docking Study of Novel Pyranocoumarin Derivatives

Abstract: A new series of fused tricyclic coumarin derivatives were designed, synthesized by a simple and convenient method, starting from 4-hydroxycoumarin and virtually screened by molecular docking on the target protein 3FRZ (PDB ID: 3FRZ), a HCV RNA-dependent RNA polymerase, for potency against hepatitis C virus (HCV). Efficient binding to the target protein was found for most of the synthesized compounds.

New in vitro highly cytotoxic platinum and palladium cyanoximates with minimal side effects in vivo

Several biologically active bivalent Pd and Pt complexes with two structurally similar cyanoxime ligands abbreviated as H(DECO): 2-oximino-2-cyano-N,N′-diethylacetamide, and H(PyrCO): 2-oximino-2-cyan-N-pyrrolidine acetamide were synthesized and characterized using spectroscopic methods, thermal analysis and X-ray crystallography. Structures revealed planar cis-geometry of studied complexes. Freshly obtained Pt(DECO)2, Pd(DECO)2, Pt(PyrCO)2 and Pd(PyrCO)2 complexes were used in for in vitro cytotoxicity assays using two different etiology human cancer cell lines HeLa and WiDr cells. Investigated compounds showed cytotoxicity levels at or above cisplatin. Pt(DECO)2 was also tested in vivo in healthy C57BL/6 mice. The complex was administered at three different dosage (0, 7.5, 15 mg/kg, i.p. once/week), over a total period of 8 weeks. No changes were observed in the animal weight in the treated mice compared to the control dextrose-treated group. The levels of erythrocytes, leukocytes, and hemoglobin were within the normal level suggesting low myelotoxicity. Negligible cardiotoxicity was observed from the histological evaluation of the hearts from the treated animals. Results from the tail nerve conduction velocity (NCV) and nerve histomorphometry suggested no impact of Pt(DECO)2 on peripheral nerves. The complex, however, induced certain hepatotoxicity and lead to the elevation of IL-6, a pro-inflammatory cytokine. Overall, Pt(DECO)2 showed minimal in vivo toxicity, thus presenting a promising candidate for future testing in animal models of cancer.

A light-up endoplasmic reticulum probe based on a rational design of red-emissive fluorogens with aggregation-induced emission

Fine-tuning electron acceptors through changing one cyano group to an amide generates a more stable and emissive fluorophore with the character of aggregation-induced emission. Conjugation between the new fluorophore and CFFKDEL generated an excellent ER targeting light-up probe with high specificity and good photostability.

Synthesis of diversely functionalised 2,2-disubstituted oxetanes: Fragment motifs in new chemical space

Di-, tri- and tetra-substituted oxetane derivatives with combinations of ester, amide, nitrile, aryl, sulfone and phosphonate substituents are prepared as fragments or building blocks for drug discovery. The synthesis of these novel oxetane functional groups, in new chemical space, is achieved via rhodium-catalysed O-H insertion and C-C bond forming cyclisation.

Synthesis of new 8-formyl-4-methyl-7-hydroxy coumarin derivatives

8-Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives were synthesized via Penchem condensation followed by Duffs reaction. Treatment of this with N,N-di substituted cyano acetamides in the presence of piperdine afforded New 8- Formyl-4-Methyl-7-Hydroxy Coumarin Derivatives (7a-o). Their structures were characterized by IR, 1H and 13C NMR and Mass spectral and elemental analysis data.

Facile and versatile room-temperature synthesis of N,n-disubstituted cyanoacetamides from malonic ester chloride

A general method for the synthesis of various N,N-disubstituted cyanoacetamides from readily available methyl malonyl chloride and secondary amines, including sterically demanding aliphatic and aromatic amines, is described.

PROCESSES FOR THE PREPARATION OF A STABLE POLYMORPHIC FORM OF ENTACAPONE

The invention relates to processes for the preparation of a stable polymorphic form of entacapone. More particularly, it relates to the preparation of stable polymorphic form designated as Form D. The invention also relates to an improved process for the preparation of 2-cyano-N,N-diethylacetamide, and to the use of this compound as an intermediate for the preparation of entacapone.

ENTACAPONE-DERIVATIVES

Pharmaceutical composition comprising one or more entacapone derivatives and one or more pharmaceutically acceptable carriers, a process for producing the pharmaceutical composition, specific entacapone derivatives, a process for the preparation of entacapone derivatives, and the use of the entacapone derivatives for the preparation of a medicament.

NOVEL CRYSTALLINE FORMS OF ENTACAPONE, AND PRODUCTION THEREOF

Disclosed are two novel crystalline forms of entacapone, form C and form D, which represent peripheral and selective COMT inhibitors that can be used for the treatment of Parkinson's disease in combination with levodopa and a decarboxylase inhibitor. Form C is produced by crystallizing entacapone from a mixture of at least one aromatic and at least one aliphatic hydrocarbon. Form D is produced by a) dissolving entacapone in a water-miscible solvent and introducing said solution into water or a mixed aqueous system, or b) dissolving entacapone in a polar aprotic or alcoholic solvent and adding said solution to an aliphatic hydrocarbon which can be mixed with said solvent and in which entacapone is insoluble, or c) crystallizing entacapone in a non-acidic solvent or a solvent mixture containing at least one non-acidic component in the presence of a strong acid, the entacapone being usable as a raw product or, in variant c), as the Knoevenagel condensation product of 3,4-dihydroxy-5-nitro-benzaldehyde and N,N-diethyl-2-cyano-acetamide, which is used in situ. Also disclosed are improvements of said Knoevenagel condensation regarding the catalyst used and regarding the production of the two components thereof, 3,4-dihydroxy-5-nitro-benzaldehyde and N,N-diethyl-2-cyano-acetamide.