25308-62-7

Basic information

• Product Name: methyl phenanthrene-1-carboxylate
• Synonyms: Methyl 1-phenanthrenecarboxylate
• CAS NO: 25308-62-7
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.2653
• Mol File: 25308-62-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 405.4°C at 760 mmHg
• Flash Point: 194.3°C
• Density: 1.208g/cm³
• Vapor Pressure: 8.81E-07mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: methyl phenanthrene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl phenanthrene-1-carboxylate(25308-62-7)
• EPA Substance Registry System: methyl phenanthrene-1-carboxylate(25308-62-7)

Safety Data

• Hazardous Substances Data: 25308-62-7(Hazardous Substances Data)

Upstream product

• 610-97-9 o-iodo-methyl-benzoic acid 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 7154-66-7 2-bromobenzoic acid chloride 
• 2039-88-5 2-bromostyrene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 38453-72-4 (E)-methyl 2-styrylbenzoate 
• 186581-53-3 diazomethane 

Downstream Products

• 26698-31-7 2-(Phenanthrene-1-carbonyl)-malonic acid diethyl ester 
• 26687-68-3 9,10-Dibromo-9,10-dihydro-phenanthrene-1-carboxylic acid 
• 26698-40-8 2-Bromo-1-phenanthren-1-yl-ethanone 
• 7473-73-6 9-Bromo-phenanthrene-1-carboxylic acid methyl ester 
• 58870-48-7 2-Bromo-1-(9-bromo-phenanthren-1-yl)-ethanone 
• 7473-68-9 9-Brom-phenanthren-1-carbonsaeure 
• 26847-77-8 9,10-Dibromo-9,10-dihydro-phenanthrene-1-carboxylic acid methyl ester 
• 26698-26-0 9-Chloro-phenanthrene-1-carboxylic acid methyl ester 
• 27875-89-4 1-phenanthrenecarboxylic acid 

Relevant articles and documents

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Cycloaddition Reaction of Vinylphenylfurans and Dimethyl Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical Alkene-Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration and DFT Understanding of Reaction Mechanisms

An experimental test of designed [8 + 2] reaction of vinylphenylfuran and dimethyl acetylenedicarboxylate (DMAD) has been carried out, showing that the reaction gave unexpected addition products under different conditions. When the reaction was conducted under thermal conditions in toluene, expoxyphenanthrene, which was named as a [8 + 2] isomer, was generated. The scope of this reaction has been investigated in the present study. In addition, experiments and DFT calculations have been conducted to investigate how the reaction between vinylphenylfuran and DMAD took place. Surprisingly, the reaction did not involve the expected [8 + 2] intermediate, o-quinodimethane. Instead, the reaction starts from intermolecular Diels-Alder reactions between DMAD and the furan moiety of vinylphenylfuran, followed by unexpected intramolecular alkene-alkene coupling. This step generates a diradical species, which then undergoes [1,3]-H shift to give the experimentally observed expoxyphenanthrene. DFT calculations revealed that, the [8 + 2] cycloadduct cannot be obtained because the [1,5]-H shift process from the [1,5]-vinyl shift intermediate is disfavored kinetically compared to the [1,3]-H shift to the [8 + 2] isomer.

Palladium-mediated total synthesis of 2-styrylbenzoic acids: A general route to 2-azachrysenes

We describe a new total synthesis of 2-styrylbenzoic acids by Heck coupling of methyl o-iodobenzoates to styrenes. Additionally, in the first general synthesis of naphtho[2,1-f]isoquinolines, these acids were transformed into phenanthrenoic acids and then