1217-49-8

Basic information

• Product Name: methyl phenanthrene-9-carboxylate
• Synonyms: methyl phenanthrene-9-carboxylate
• CAS NO: 1217-49-8
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.26
• Mol File: 1217-49-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 405.4°Cat760mmHg
• Flash Point: 194.3°C
• Appearance: /
• Density: 1.208g/cm³
• Vapor Pressure: 8.81E-07mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: methyl phenanthrene-9-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl phenanthrene-9-carboxylate(1217-49-8)
• EPA Substance Registry System: methyl phenanthrene-9-carboxylate(1217-49-8)

Safety Data

• Hazardous Substances Data: 1217-49-8(Hazardous Substances Data)

Usage

General Description

Methyl phenanthrene-9-carboxylate is a chemical compound with the molecular formula C17H12O2. It is a methyl ester of phenanthrene-9-carboxylic acid, which is a derivative of phenanthrene, a polycyclic aromatic hydrocarbon. This chemical is used in various industrial applications, including as a precursor in the synthesis of other organic compounds and as a component in the production of certain pharmaceuticals. It is also used as a research tool in the study of organic chemistry and as a reference standard in analytical chemistry. Methyl phenanthrene-9-carboxylate is a white to off-white solid with a molecular weight of 248.27 g/mol, and it is typically handled and stored in accordance with standard chemical safety practices.

InChI:InChI=1/C16H12O2/c1-18-16(17)15-10-11-6-2-3-7-12(11)13-8-4-5-9-14(13)15/h2-10H,1H3

Upstream product

• 67-56-1 methanol 
• 166042-86-0 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one 
• 151-50-8 potassium cyanide 
• 90-41-5 2-phenylaniline 
• 922-67-8 propynoic acid methyl ester 
• 3186-53-6 O-methyl S-p-methylphenyl thiocarbonate 
• 68572-87-2 9-phenanthrenylboronic acid 

Downstream Products

• 83665-36-5 (1R,2S,2aS)-2-(4-Methoxy-phenyl)-1-methyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carboxylic acid methyl ester 
• 85-01-8 phenanthrene 
• 883-20-5 9-methylphenanthrene 

Relevant articles and documents

Palladium-Catalyzed, Copper(I)-Promoted Methoxycarbonylation of Arylboronic Acids with O-Methyl S-Aryl Thiocarbonates

Here, we report O-methyl S-aryl thiocarbonates as a versatile esterification reagent for palladium-catalyzed methoxycarbonylation of arylboronic acid in the presence of copper(I) thiophene-2-carboxylate (CuTC). The reaction condition is mild, and a variety of substituents including sensitive-Cl,-Br, and free-NH2 could be tolerated. Further applications in the late-stage esterification of some pharmaceutical drugs demonstrate the broad utility of this method.

Sandmeyer reactions. Part 6. A mechanistic investigation into the reduction and ligand transfer steps of Sandmeyer cyanation

For Sandmeyer cyanation at 298 K in 50% v/v aqueous acetonitrile buffered at pH 8, absolute rate constants have been obtained for the reduction of 4-methoxybenzenediazonium tetrafluoroborate by the cyanocuprate(I) anions Cu1(CN)43-, Cu1(NCMe)(CN)32- and Cu1(NCMe)2(CN)2- as (0.50 ± 0.05), (0.12 ± 0.03) and 0.0 dm3 mol-1 s-1, respectively. The relative reactivity of the two reactive cyanocuprates reflects the estimated difference in their standard reduction potentials. Ligand transfer to the aryl radical from the cyanocuprate(II) anions produced in the reaction occurs within the solvent cage. By use of radical clocks, first order rate constants of the order of 1 × 108 s-1 for ligand transfer between the caged reactants can be evaluated although the transfer rate may vary from one aryl radical to another. No difference was discerned in ligand transferring reactivity between the two cyanocuprate(II) complexes involved.

Synthesis and Photochemistry of 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one. Generation and Reactions of Phenanthrenodiazacyclopentadiene, Phenanthrenocyclopropenone, and 9,10-Phenanthryne

The title compound 15 was prepared as the first 1,3-bis(diazo) ketone incorporated into a seven-membered ring, and its photochemical pathways were investigated not only by product analysis study but also by using matrix isolation spectroscopy.Irradiation of 15 in alcoholic solvents gave 9-(alkoxycarbonyl)phenanthrene 16 as a main product, while similar irradiation in non-nucleophilic solvents provided diphenanthreno-syn-1,5-diazabicyclooctadienedione (20).The formation of these products is interpreted as indicating that 15 eliminates one of two diazo functions upon photoexcitation to form 9-diazo-10-carbonylphenanthrene (21) which either reacts with alcohol by eliminating the second dinitrogen, leading to 16, or undergoes dimerization to form 20.Photolysis of 15 in an ethanol matrix at 77 K gave 9-ethoxyphenanthrene (31) as a new product along with 16.Irradiation of 15, matrix-isolated in Ar at 10 K monitored by IR, indicated that phenanthrenocyclopropenone (28) was formed as an initial product which then underwent photodecarbonylation to leave 9,10-phenanthryne (32), and that 32 reacted with CO to reproduce 28 upon photoexcitation.The cyclopropenone (28) was shown to be generated also by photolysis of 9,10-dicarboxyphenanthrene anhydride (33) in Ar matrix at 10 K.A plausible mechanism to explain the observed sequential decomposition of the two diazo functions in the room temperature photolytic run and the formal simultaneous elimination of two dinitrogens in the low temperature matrix run is proposed.