5891-25-8

Basic information

• Product Name: 4,4-dimethylpent-1-yn-3-one
• Synonyms: 4,4-Dimethyl-1-pentyne-3-one; Pent-4-yn-3-one, 2,2-dimethyl-
• CAS NO: 5891-25-8
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.1537
• Mol File: 5891-25-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 144.1°C at 760 mmHg
• Flash Point: 45.8°C
• Density: 0.881g/cm³
• Vapor Pressure: 5.17mmHg at 25°C
• Refractive Index: 1.43
• CAS DataBase Reference: 4,4-dimethylpent-1-yn-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-dimethylpent-1-yn-3-one(5891-25-8)
• EPA Substance Registry System: 4,4-dimethylpent-1-yn-3-one(5891-25-8)

Safety Data

• Hazardous Substances Data: 5891-25-8(Hazardous Substances Data)

Upstream product

• 64214-60-4 N-methoxy-N-methylpivalamide 
• 61317-72-4 4,4-dimethylpent-1-yn-3-ol 
• 3282-30-2 pivaloyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 1066-54-2 trimethylsilylacetylene 
• 53723-94-7 4,4-dimethyl-1-(trimethylsilyl)pent-1-yn-3-one 

Downstream Products

• 1003-86-7 3-tert-butyl-isoxazole 
• 1122-01-6 5-tert-Butyl-isoxazol 
• 1207535-16-7 3-(2,4,6-trimethoxyphenyl)-1-t-butyl-2-propyn-1-one 

Relevant articles and documents

Gold-catalyzed ethynylation of arenes

(Figure Presented) A novel gold-catalyzed ethynylation of aromatic rings with electron-deficient alkynes via gold catalyzed C-H activation of both C sp-H and Csp2-H bonds has been developed. This transformation provides aromatic propiolates difficult to prepare by other methods, highlighting the synthetic potential of gold chemistry.

Asymmetric reduction of ethynyl ketones and ethynylketoesters by secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus

Secondary alcohol dehydrogenase (SADH) from Thermoanaerobacter ethanolicus, an NADP-dependent, thermostable oxidoreductase, reduces ethynyl ketones and ethynylketoesters enantioselectively to the corresponding propargyl (propargyl = prop-2-ynyl) alcohols. Ethynyl ketones, in general, are reduced with moderate enantioselectivity (with the exception of 4-methylpent-l-yn-3-one, which gives the (S)-alcohol with >98% ee). Although ethynyl ketones bearing a small (up to n-propyl) alkyl substituent are reduced to (S)-alcohols, larger ethynyl ketones give (R)-alcohols. In contrast, ethynylketoesters are converted to (R)-ethynylhydroxyesters of excellent optical purity. Unexpectedly, isopropyl ethynylketoesters give higher chemical yields and higher enantioselectivities of ethynylhydroxyesters than methyl or ethyl ethynylketoesters. The optically pure ethynylhydroxyesters may serve as useful chiral building blocks for asymmetric synthesis.

A convenient synthesis of masked β-ketoaldehydes by the controlled addition of nucleophiles to (trimethylsilyl)ethynyl ketones

The controlled addition of nucleophiles to (trimethylsilyl)ethynyl ketones provides a facile route to β-ketoacetals, β-alkoxy-α,β-unsaturated ketones or vinylogous amides depending on the choice of reaction conditions.