39581-30-1

Basic information

• Product Name: 2-cyano-N-methyl-N-phenylacetamide
• Synonyms: 2-cyano-N-methyl-N-phenylacetamide
• CAS NO: 39581-30-1
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.1992
• Mol File: 39581-30-1.mol

Chemical Properties

• Melting Point: 76-78 °C(Solv: ethyl acetate (141-78-6); isopropyl ether (108-20-3))
• Boiling Point: 312.1±25.0 °C(Predicted)
• Appearance: /
• Density: 1.154±0.06 g/cm3(Predicted)
• PKA: -2.73±0.10(Predicted)
• CAS DataBase Reference: 2-cyano-N-methyl-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-N-methyl-N-phenylacetamide(39581-30-1)
• EPA Substance Registry System: 2-cyano-N-methyl-N-phenylacetamide(39581-30-1)

Safety Data

• Hazardous Substances Data: 39581-30-1(Hazardous Substances Data)

Upstream product

• 474897-06-8 N-methyl-N-phenyl malondiamide 
• 16130-58-8 cyanoacetic acid chloride 
• 100-61-8 N-methylaniline 
• 372-09-8 cyanoacetic acid 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 175687-69-1 N-methyl-N-phenyl-α-diazo-2-cyanoacetamide 
• 74-90-8 hydrogen cyanide 
• 13120-33-7 2-(methyl(phenyl)amino)-2-oxoacetic acid 
• 247099-40-7 C₁₇H₁₄N₂O 
• 900714-64-9 C₁₈H₁₆N₂O₂ 
• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 1537188-58-1 C₁₇H₁₂N₂O₂ 
• 1266983-01-0 C₁₇H₁₆N₂O 

Relevant articles and documents

Three-component couplings for the synthesis of pyrroloquinoxalinones by azomethine ylide 1,3-dipolar cycloaddition chemistry

1-Methyl-3,4-dihydroquinoxalin-2(1H)-one was heated with a range of aldehydes to generate intermediate azomethine ylides which underwent [3 + 2] cycloaddition reactions with N-methyl or N-phenylmaleimide to give substituted tetrahydropyrroloquinoxalinones

One-Pot Synthesis of Quinoxalinones via Tandem Nitrosation/Cyclization of N-Aryl Cyanoacetamides

A new one-pot strategy for the synthesis of quinoxalin-2-ones from the tandem nitrosation/cyclization reaction of N-aryl cyanoacetamides with tert-butyl nitrite has been developed. The dehydrogenative N-incorporation is achieved through a sequence of nitrosation, tautomerization, and cyclization, affording quinoxalin-2-ones in moderate to good yields with good functional group tolerance.

3-Alkylperoxy-3-cyano-oxindoles from 2-Cyano-2-diazo-N-phenyl-acetamides via Cyclizing Carbene Insertion and Subsequent Radical Oxidation

A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion

Expeditious and Convenient Synthesis of Polycyclic Difluoroboron Complexes of 2-Oxoindoline-3-carboxamides by Tandem Reaction

N-Aryl-2-cyanodiazoacetamides produce polycyclic difluoroboron 2-oxoindoline-3-carboxamide complexes (up to pentacyclic conjugative and fused systems) directly and expeditiously in the presence of boron trifluoride etherate. The boron trifluoride serves as both a catalyst and reactant in the tandem reaction. The tandem reaction includes the carbene aromatic C-H insertion, hydrolysis of the cyano group into an amide group, and boronation of the two amide carbonyl groups. The synthetic method features the advantages of wide substrate scope and excellent chemoselectivity.

Chemospecific synthesis of 2-acetoxyindole-3-carbonitriles catalyzed by Cu(acac)2

A chemospecific one-pot synthesis of easily isolable 2-acetoxyindole-3-carbonitriles was described. The intermediate 2-oxindole-3-carbonitriles successfully prepared from 2-cyano diazoacetanilides without isolation were treated with acetyl chloride and tr

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.

A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides

The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

Triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides: a concise synthesis of glycocitlone alkaloids

A method is presented for the concise synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones through triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides. This tandem process was successfully used for the rapid syntheses of glycocitl

Ligand effects in the rhodium(II) catalysed reactions of diazoamides and diazoimides

A range of substituted α-diazoamides 1-8 and diazoimides 9-12 was prepared from the corresponding amines or amides. Rhodium(II) catalysed decomposition of the diazoamides resulted in attack on the aromatic ring to give oxindoles or attack on the alkyl group to give either β-lactams or cycloheptapyrrolones. The chemoselectivity of the rhodium carbenoid intermediate was dependent on the metal ligands, fluorinated carboxamides strongly promoting attack on aromatic rings in preference to other processes. Decomposition of the diazoimides resulted in intramolecular attack on the carbonyl group to give an ylide which could be trapped inter- or intramolecularly. X-Ray crystal structures are reported for the diazo compounds 2 and 4, the indoles 17 and 25, the β-lactam 20, the cycloheptapyrrolones 24 and 28, the dimer 29 and the Pictet Spengler product 39.