1005-42-1

Upstream product

• 75-20-7 calcium carbide 
• 591-27-5 m-Hydroxyaniline 
• 74-86-2 acetylene 

Downstream Products

• 86303-34-6 4-(4-Nitro-phenylazo)-3-vinyloxy-phenylamine 
• 86303-33-5 2-vinyloxy-4-aminoazobenzene 
• 86303-35-7 4-(4-Amino-2-vinyloxy-phenylazo)-benzoic acid 
• 86303-36-8 4-(4-Amino-2-vinyloxy-phenylazo)-benzenesulfonic acid 
• 86269-45-6 2-Hydroxy-N-(3-vinyloxy-phenyl)-benzamide 
• 1214923-75-7 (1S,2S,3R,4R)-3-(2-(3-(allyloxy)phenylamino)-5-fluoropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide 

Relevant academic research and scientific papers

An Atom-Economic Approach for Vinylation of Indoles and Phenols Using Calcium Carbide as Acetylene Surrogate

An efficient N-vinylation of indoles and O-vinylation of phenols to give N-vinyl indoles and phenyl vinyl ethers is reported. The vinylated products can be produced in satisfactory to excellent yields (65–92 %) upon treatment of indoles or phenols with calcium carbide in wet solvents in a standard laboratory setup. Key features of this reaction include the use of calcium carbide as a safe and inexpensive slow released acetylene source for N- and O-vinylation under simple reaction conditions without the need for metal catalyst or halogenated substrates.

Chemoselective vinylation of aminophenols with acetylene catalyzed by sodium aminophenolates in aqueous DMSO

An efficient atom-economic chemoselective synthesis of vinyloxyanilines from aminophenols and acetylene catalyzed by sodium aminophenolates in aqueous DMSO (90 °C, 3 h) has been developed.

Direct vinylation of natural alcohols and derivatives with calcium carbide

Vinyl ethers are essential synthetic building blocks for organic synthesis, especially for polymer synthesis and highly vinylated polyol substrates. Herein, a transition metal-free, mild, and safe protocol has been developed for direct vinylation of natural alcohols with calcium carbide. Various sugar alcohols, phenol and its derivatives were tested and proved successful using this green methodology. Selectivity of full vinylated products of the reaction decreases with increasing hydroxyl groups because of side reactions occurring under the basic medium. Electron-donating substituted phenols work more efficiently than electron-withdrawing substituted phenols in general. This methodology may provide new insights on selective vinylation of electron-rich biomass-derived materials.