methyl (Z)-3-phenanthren-9-ylprop-2-enoate

Base Information

• Chemical Name: methyl (Z)-3-phenanthren-9-ylprop-2-enoate
• CAS No.: 7470-23-7
• Molecular Formula: C₁₈H₁₄O₂
• Molecular Weight: 262.308
• NSC Number: 402394
• DSSTox Substance ID: DTXSID30419661
• Wikidata: Q82230799
• Mol file: 7470-23-7.mol

Synonyms:NSC402394;7470-23-7;DTXSID30419661;NSC-402394

Chemical Property of methyl (Z)-3-phenanthren-9-ylprop-2-enoate

Chemical Property:

• Vapor Pressure: 1.93E-08mmHg at 25°C
• Boiling Point: 454.3°Cat760mmHg
• Flash Point: 307.9°C
• Density: 1.199g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 262.099379685
• Heavy Atom Count: 20
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC2=CC=CC=C2C3=CC=CC=C31
• Isomeric SMILES: COC(=O)/C=C\C1=CC2=CC=CC=C2C3=CC=CC=C31

Technology Process of methyl (Z)-3-phenanthren-9-ylprop-2-enoate

There total 5 articles about methyl (Z)-3-phenanthren-9-ylprop-2-enoate 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: 90.0%

9-bromophenanthrene (573-17-1) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (E)-3-(phenanthren-9-yl)acrylate (7470-23-7,22844-32-2)

Guidance literature:

With [CH₃PPh₃]₂[Pd₂Br₂Cl₄]; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 140 ℃; for 0.833333h;

DOI:10.1055/s-0032-1317963

Reference yield:

methyl 3-(phenanthren-9-yl)propiolate → methyl (E)-3-(phenanthren-9-yl)acrylate (7470-23-7,22844-32-2) + methyl 3-(9-phenanthryl)propanoate (5328-28-9) + methyl (Z)-3-(phenanthren-9-yl)acrylate

Guidance literature:

With hydrogen; In N,N-dimethyl-formamide; at 40 ℃; for 11h; Schlenk technique;

DOI:10.1002/adsc.202000208

Reference yield:

Phenanthrene-9-carboxaldehyde (4707-71-5) → methyl (E)-3-(phenanthren-9-yl)acrylate (7470-23-7,22844-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: acetone; diethyl ether

With pyridine; diethyl ether; acetone;

DOI:10.1021/ja01290a034

upstream raw materials:

diazomethane

trans-β-(9-phenanthryl)acrylic acid

9-bromophenanthrene

acrylic acid methyl ester