Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester

Base Information

• Chemical Name: Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester
• CAS No.: 654074-74-5
• Molecular Formula: C12H14I2O3
• Molecular Weight: 460.05
• DSSTox Substance ID: DTXSID10477547
• Wikidata: Q82310318
• Mol file: 654074-74-5.mol

Synonyms:654074-74-5;Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester;DTXSID10477547

Chemical Property of Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 459.90324
• Heavy Atom Count: 17
• Complexity: 236

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)I)OCCCC(=O)OC)I

Technology Process of Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester

There total 1 articles about Butanoic acid, 4-(2,6-diiodo-4-methylphenoxy)-, methyl ester 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: 73.0%

2,6-diiodo-4-methylphenol (2432-18-0) + trimethyl ortho-4-bromobutanoate (55444-67-2) → methyl 4-(2,6-diiodo-4-methyl)phenoxybutyrate (654074-74-5)

Guidance literature:

2,6-diiodo-4-methylphenol; trimethyl ortho-4-bromobutanoate; With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 60 ℃; for 48h;

With acetic acid; In dichloromethane;

DOI:10.1021/ja038484x

Reference yield: 87.0%

1,4-dipropyloxy-2-ethynyl-5-(2-triisopropylsilylethinyl)benzene (221292-51-9) + methyl 4-(2,6-diiodo-4-methyl)phenoxybutyrate (654074-74-5) → methyl-4-(2,6-bis{2-[2,5-dipropyloxy-4-(2-triisopropylsilylethynyl)phenyl]ethynyl}-4-methyl)phenoxybutyrate (654074-75-6)

Guidance literature:

In tetrahydrofuran; triethylamine; at 20 - 50 ℃; for 25h;

DOI:10.1021/ja038484x

Reference yield:

methyl 4-(2,6-diiodo-4-methyl)phenoxybutyrate (654074-74-5) → methyl-4-{2,6-bis[2-(2,5-dipropyloxy-4-{2-[3-(tetrahydro-2H-pyran-2-yloxy)-5-ethynylphenyl]ethynyl}phenyl)ethynyl]-4-methyl}phenoxybutyrate (654074-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / triethylamine; tetrahydrofuran / 25 h / 20 - 50 °C

2: 74 percent / aq. Bu₄NF / tetrahydrofuran / 2 h / 20 °C

3: 81 percent / Pd(PPh₃)2Cl₂; CuI / triethylamine / 18 h / 60 °C

4: 86 percent / Pd(PPh₃)2Cl₂; CuI; piperidine / 16 h / 60 °C

5: 89 percent / K₂CO₃; MeOH / tetrahydrofuran / 26 h / 20 °C

With piperidine; methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; triethylamine; 1: Hagihara-Sonogashira coupling;

DOI:10.1021/ja038484x

upstream raw materials:

2,6-diiodo-4-methylphenol

trimethyl ortho-4-bromobutanoate

Downstream raw materials:

methyl-4-(2,6-bis{2-[2,5-dipropyloxy-4-(2-triisopropylsilylethynyl)phenyl]ethynyl}-4-methyl)phenoxybutyrate

methyl-4-{2,6-bis[2-(2,5-dipropyloxy-4-ethynylphenyl)ethynyl]-4-methyl}phenoxybutyrate

methyl-4-{2,6-bis[2-(2,5-dipropyloxy-4-{2-[5-iodo-3-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethynyl}phenyl)ethynyl]-4-methyl}phenoxybutyrate

methyl-4-{2,6-bis[2-(2,5-dipropyloxy-4-{2-[3-(tetrahydro-2H-pyran-2-yloxy)-5-ethynylphenyl]ethynyl}phenyl)ethynyl]-4-methyl}phenoxybutyrate