methyl phenanthrene-9-carboxylate

Base Information

• Chemical Name: methyl phenanthrene-9-carboxylate
• CAS No.: 1217-49-8
• Molecular Formula: C16H12O2
• Molecular Weight: 236.27
• Hs Code.: 2916399090
• Mol file: 1217-49-8.mol

Synonyms:9-(Carbomethoxy)phenanthrene;Methyl 9-phenanthroate;Methyl phenanthrene-9-carboxylate;NSC 17522;

Chemical Property of methyl phenanthrene-9-carboxylate

Chemical Property:

• Vapor Pressure: 8.81E-07mmHg at 25°C
• Refractive Index: 1.677
• Boiling Point: 405.4°Cat760mmHg
• Flash Point: 194.3°C
• PSA: 26.30000
• Density: 1.208g/cm³
• LogP: 3.77960

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl phenanthrene-9-carboxylate

There total 5 articles about methyl phenanthrene-9-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

O-methyl S-p-methylphenyl thiocarbonate (3186-53-6) + 9-phenanthrenylboronic acid (68572-87-2) → 9-(methoxycarbonyl)phenanthrene (1217-49-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane; In 1,4-dioxane; at 60 ℃; for 16h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.0c00198

Reference yield: 64.0%

2-phenylaniline (90-41-5) + propynoic acid methyl ester (922-67-8) → biphenyl (92-52-4,1594-86-1) + 9-(methoxycarbonyl)phenanthrene (1217-49-8)

Guidance literature:

With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); tert.-butylnitrite; In acetonitrile; at 20 ℃; Sealed tube; Irradiation;

DOI:10.1021/acs.joc.7b00413

Reference yield: 41.0%

methanol (67-56-1) + 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one (166042-86-0) → phenanthrene (85-01-8) + methyl 9,10-dihydro-9-phenanthrenecarboxylate (32892-19-6) + 9-(methoxycarbonyl)phenanthrene (1217-49-8)

Guidance literature:

Ambient temperature; Irradiation;

DOI:10.1021/jo00113a011

upstream raw materials:

methanol

5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one

potassium cyanide

2-phenylaniline

Downstream raw materials:

phenanthrene

(1R,2S,2aS)-2-(4-Methoxy-phenyl)-1-methyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carboxylic acid methyl ester

9-methylphenanthrene

Refernces

• 1、 Chatterjee, Tanmay,Lee, Da Seul,Cho, Eun Jin. "Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics". . p. 4369 - 4378. Retrieved 2017/04/28.
• 2、 Hanson, Peter,Loevenich, P. Wilfried,Rowell, Simon C.,Walton, Paul H.,Timms, Allan W.. "Sandmeyer reactions. Part 4. An investigation into the cyclisation modes of Pschorr phenanthrene synthesis". . p. 49 - 64. Retrieved 2007/10/03.