24813-24-9

Basic information

• Product Name: N-(tricyclo[3.3.1.1~3,7~]dec-1-yl)pyridine-4-carboxamide
• Synonyms: 4-pyridinecarboxamide, N-tricyclo[3.3.1.1~3,7~]dec-1-yl-; N-(Adamantan-1-yl)isonicotinamide
• CAS NO: 24813-24-9
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.3428
• Mol File: 24813-24-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 466.7°C at 760 mmHg
• Flash Point: 236.1°C
• Density: 1.19g/cm³
• Vapor Pressure: 6.91E-09mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: N-(tricyclo[3.3.1.1~3,7~]dec-1-yl)pyridine-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tricyclo[3.3.1.1~3,7~]dec-1-yl)pyridine-4-carboxamide(24813-24-9)
• EPA Substance Registry System: N-(tricyclo[3.3.1.1~3,7~]dec-1-yl)pyridine-4-carboxamide(24813-24-9)

Safety Data

• Hazardous Substances Data: 24813-24-9(Hazardous Substances Data)

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 768-95-6 1-adamanthanol 
• 1120-87-2 4-bromopyridin 
• 768-94-5 1-Adamantanamine 
• 55-22-1 pyridine-4-carboxylic acid 

Relevant articles and documents

Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcohols, and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki–Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.

Highly efficient synthesis of amides via Ritter chemistry with ionic liquids

The utility of Br?nsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf] as catalyst for the high yield synthesis of a wide variety of amides under mild conditions via the Ritter reaction of alcohols with nitriles has been demonstrated. As alternative methods for the carbocation generation step, NOPF6 immobilized in [BMIM][PF6] ionic liquid was used in the Ritter reaction of bromides with nitriles and for the synthesis of adamantyl amides from adamantane and nitriles.