4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid

Base Information

• Chemical Name: 4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid
• CAS No.: 161692-81-5
• Molecular Formula: C17H12 F2 O3
• Molecular Weight: 302.277
• DSSTox Substance ID: DTXSID90167212
• Nikkaji Number: J874.550A
• Wikidata: Q83036537
• Mol file: 161692-81-5.mol

Synonyms:161692-81-5;4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid;(1,1'-Biphenyl)-4-butanoic acid, 2',4'-difluoro-alpha-methylene-gamma-oxo-;2',4'-Difluoro-alpha-methylene-gamma-oxo-(1,1'-biphenyl)-4-butanoic acid;SCHEMBL599291;DTXSID90167212;CKUYHCQGMBHTTK-UHFFFAOYSA-N;C17H12F2O3;LS-44174;2-[2-(2',4'-difluoro[1,1'-biphenyl]-4-yl)-2-oxoethyl]acrylic acid;4-(2',4'-Difluoro-1,1'-biphenyl-4-yl)-2-methylene-4-oxobutyric acid

Chemical Property of 4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid

Chemical Property:

• Boiling Point: 490.4°Cat760mmHg
• PKA: 3.73±0.11(Predicted)
• Flash Point: 250.4°C
• PSA: 54.37000
• Density: 1.293g/cm³
• LogP: 3.84540
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 302.07545056
• Heavy Atom Count: 22
• Complexity: 441

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C(CC(=O)C1=CC=C(C=C1)C2=C(C=C(C=C2)F)F)C(=O)O

Technology Process of 4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid

There total 2 articles about 4-(2',4'-Difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid 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: 63.0%

2,4-difluorobiphenyl (37847-52-2) + itaconic acid anhydride (2170-03-8) → 4-(2',4'-difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid (161692-81-5)

Guidance literature:

With aluminium trichloride; In dichloromethane; 1.) 10 deg C, 4 h, 2.) 20 deg C, 2 h;

DOI:10.1135/cccc19942705

Reference yield:

2-methylenesuccinic acid (97-65-4,25119-64-6) → 4-(2',4'-difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid (161692-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Ac₂O / 4 h / 80 °C

2: 63 percent / AlCl₃ / CH₂Cl₂ / 1.) 10 deg C, 4 h, 2.) 20 deg C, 2 h

With aluminium trichloride; acetic anhydride; In dichloromethane;

DOI:10.1135/cccc19942705

Reference yield: 74.0%

4-(2',4'-difluorobiphenyl-4-yl)-2-methylene-4-oxobutanoic acid (161692-81-5) → 4-(2',4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid (112344-52-2,104941-35-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; at 20 ℃; under 3750.3 Torr;

DOI:10.1135/cccc19942705

upstream raw materials:

2,4-difluorobiphenyl

itaconic acid anhydride

2-methylenesuccinic acid

Downstream raw materials:

4-(2',4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid

5-(2',4'-Difluoro-biphenyl-4-yl)-5-hydroxy-3-methyl-5H-furan-2-one

Refernces