108168-88-3

Basic information

• Product Name: N-tert-butyl-2-cyanoacetamide
• Synonyms: N-tert-butyl-2-cyanoacetamide;N-(tert-butyl)-2-cyanoacetamide(WXC07999)
• CAS NO: 108168-88-3
• Molecular Formula: C₇H₁₂N₂O
• Molecular Weight: 140.18298
• Mol File: 108168-88-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 306.9±25.0 °C(Predicted)
• Appearance: /
• Density: 0.977±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.69±0.10(Predicted)
• CAS DataBase Reference: N-tert-butyl-2-cyanoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butyl-2-cyanoacetamide(108168-88-3)
• EPA Substance Registry System: N-tert-butyl-2-cyanoacetamide(108168-88-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 108168-88-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 3235, 1990 DOI: 10.1080/00397919008051551

Upstream product

• 75-64-9 tert-butylamine 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 
• 119072-55-8 tert-butylisonitrile 
• 590-17-0 cyanomethyl bromide 
• 15678-99-6 N-tert-butylchloroacetamide 
• 109-77-3 malononitrile 
• 75-65-0 tert-butyl alcohol 
• 16130-58-8 cyanoacetic acid chloride 
• 75-05-8 acetonitrile 
• 1609-86-5 Tert-butyl isocyanate 
• 105-56-6 ethyl 2-cyanoacetate 
• 131297-21-7 5-(Bis-tert-butylamino-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 

Relevant articles and documents

Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals

A new visible light-induced photocatalytic protocol enabling the formation of secondary amides from electron-poor organic bromides and isocyanides was developed. In addition, the in situ interception of ketenimine intermediates with nitrogen nucleophiles such as amines, hydrazines, and TMSN3 afforded, in a one-pot two-step procedure, valuable scaffolds such as ketene aminals, pyrazolones, and tetrazoles. Mechanistic evidence confirmed a radical pathway where isocyanides acted as radical geminal acceptors generating key imidoyl radical species.

Synthesis, cytotoxic characterization, and SAR study of imidazo[1,2-b]pyrazole-7-carboxamides

The synthesis and in vitro cytotoxic characteristics of new imidazo[1,2-b]pyrazole-7-carboxamides were investigated. Following a hit-to-lead optimization exploiting 2D and 3D cultures of MCF-7 human breast, 4T1 mammary gland, and HL-60 human promyelocytic leukemia cancer cell lines, a 67-membered library was constructed and the structure–activity relationship (SAR) was determined. Seven synthesized analogues exhibited sub-micromolar activities, from which compound 63 exerted the most significant potency with a remarkable HL-60 sensitivity (IC50 = 0.183 μM).

Application of SiO2-Pr-SO3H as an efficient catalyst in the Ritter reaction

Sulfonic-acid-functionalized silica was applied as an efficient heterogeneous acid catalyst in the Ritter reaction to prepare amides by reaction of various benzylic, allylic, and tertiary alcohols with various nitriles in good to excellent yields under solvent-free conditions. The simplicity of the reaction, recovery of catalyst without loss of reactivity, high yield of products, and short reaction time represent improvements over many existing methods.