819871-78-8

Basic information

• Product Name: Benzene, 1-ethynyl-2-(2-methyl-1-propenyl)-
• CAS NO: 819871-78-8
• Molecular Formula: C12H12
• Molecular Weight: 156.227
• Mol File: 819871-78-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-ethynyl-2-(2-methyl-1-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-ethynyl-2-(2-methyl-1-propenyl)-(819871-78-8)
• EPA Substance Registry System: Benzene, 1-ethynyl-2-(2-methyl-1-propenyl)-(819871-78-8)

Safety Data

• Hazardous Substances Data: 819871-78-8(Hazardous Substances Data)

Upstream product

• 819871-77-7 1-(2-methylprop-1-enyl)-2-[2-(trimethylsilyl)ethynyl]benzene 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 34472-48-5 1-(1-methylethylidene)-1H-indene 
• 573-98-8 dimethyl-1,2 naphtalene 
• 38740-43-1 2-(prop-1-en-2-yl)-1H-indene 
• 1562-94-3 4,4'-dimethoxyazoxybenzene 
• 1322670-31-4 1-(2-methylprop-1-en-1-yl)-2-(prop-1-yn-1-yl)benzene 
• 1638606-47-9 C₁₉H₁₉N₃O₂S 

Relevant articles and documents

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

Silver-catalyzed stereoselective [3+2] cycloadditions of cyclopropyl-indanimines with carbonyl compounds

Silver-catalyzed stereoselective [3+2] cycloadditions between mono-substituted cyclopropyl-indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change of stereochemistry for the resulting indanone products. Copyright

Rutheniun-catalyzed cycloisomerization of o-(ethynyl)phenylalkenes to diene derivatives via skeletal rearrangement

Treatment of a series of 2′,2′-disubstituted (oethynyl)styrenes with TpRu(PPh3)(CH3CN)2PF6 (10 mol %) in benzene (80°C, 12-18 h) efficiently gave 2-alkenyl-1H-indene derivatives. This catalytic reaction represents an atypical enyne cycloisomerization with skeletal rearrangement of starting enyne, where the C=C bond is completely cleaved and inserted by the terminal alkynyl carbon. The reaction mechanism was elucidated by a series of deuterium and 13C labeling experiments, as well as by changing the substituents at the phenyl moieties. The mechanism is proposed to involve the following key steps: 5-endo-dig cyclization of ruthenium-vinylidene intermediate, a nonclassical ion formation, and the "methylenecyclopropane-trimethylenemethane" rearrangement.