7138-42-3

Usage

Physical properties

colorless liquid with a fruity odor

Common use

solvent in industrial processes

Other uses

synthesis of other chemicals, potential applications in pharmaceutical and agricultural industries

Classification

hazardous material (flammable, potential health risks)

Important note

requires careful handling to ensure safety

Upstream product

• 78-95-5 chloroacetone 
• 693-02-7 hex-1-yne 
• 17603-76-8 2-methyl-1-octen-3-yne 
• 17689-03-1 1-hexynyllithium 

Downstream Products

• 149382-89-8 4-(tert-Butyl-diphenyl-silanyl)-2-methyl-octa-2,3-dienal 
• 233595-58-9 2-(1,2-propadienyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 
• 20599-16-0 2-methyloct-3-yn-2-ol 
• 50994-76-8 2-methyl-2,3-octadienol 
• 14502-95-5 2-methyloct-3-yn-1-ol 
• 146232-15-7 2-methylene-4-n-butylbut-3-yn-1-ol 
• 149382-86-5 4-(tert-Butyl-diphenyl-silanyl)-2-methyl-octa-2,3-dien-1-ol 

Relevant academic research and scientific papers

Borylation of propargylic substrates by bimetallic catalysis. Synthesis of allenyl, propargylic, and butadienyl bpin derivatives

Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S N2′ pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

Silver(I)-catalyzed cascade: Direct access to furans from alkynyloxiranes

(Chemical Equation Presented) Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.

Catalytic scaffolding ligands: An efficient strategy for directing reactions

The design and application of a scaffolding ligand that promotes branch and diastereoselective hydroformylation of terminal olefins as well as the regio- and diastereoselective hydroformylation of disubstituted olefins is reported. It is shown that the ligand covalently and reversibly bonds to the substrate, allowing for directed hydroformylation. As the substrate ligand interaction is dynamic, hydroformylations are catalytic in ligand and do not require any additional synthetic steps to add or remove the directing group. Using a catalytic quantity of a scaffolding ligand (20-25 mol %), excellent regioselectivity for disubstituted olefins (up to 98:2) and high branch selectivity (up to 88:12) for terminal olefins were obtained. Copyright

Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates: Synthetic route to α-amino allenes and Δ3-pyrrolines

(Chemical Equation Presented) Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)-alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2′ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2′ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.

Regioselective ring opening of α-substituted α-alkynyl oxiranes to 2-substituted 3-butyn-1-ols

Treatment of α-substituted α-acetylenic epoxides with DIBAH in THF provides 2-substituted 3-butyn-1-ols in high yield avoiding propargyl/allene isomerization.