80151-20-8

Basic information

• Product Name: Benzonitrile, 4-(3-hydroxy-3-methyl-1-butynyl)-
• CAS NO: 80151-20-8
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Mol File: 80151-20-8.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(3-hydroxy-3-methyl-1-butynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(3-hydroxy-3-methyl-1-butynyl)-(80151-20-8)
• EPA Substance Registry System: Benzonitrile, 4-(3-hydroxy-3-methyl-1-butynyl)-(80151-20-8)

Safety Data

• Hazardous Substances Data: 80151-20-8(Hazardous Substances Data)

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 3058-39-7 4-iodobenzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 7681-65-4 copper(I) iodide 
• 7440-05-3 palladium 

Downstream Products

• 1360703-65-6 (Z)-4-((3-benzoyl-5,5-dimethyl-2-oxooxazolidin-4-ylidene)methyl)benzonitrile 

Relevant articles and documents

Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

Diimine (HN═NH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.

Rhodium-catalyzed oxidative coupling of benzoic acids with propargyl alcohols: An efficient access to isocoumarins

An efficient protocol of Rh(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins under mild conditions was reported. A variety of substrates were applied in this reaction in yields up to 89%.

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.