Methyl 3',4'-dichloro[1,1'-biphenyl]-4-carboxylate

Base Information

• Chemical Name: Methyl 3',4'-dichloro[1,1'-biphenyl]-4-carboxylate
• CAS No.: 886362-11-4
• Molecular Formula: C₁₄H₁₀Cl₂O₂
• Molecular Weight: 281.138
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID90594726
• Nikkaji Number: J2.107.196J
• Wikidata: Q82489631
• Mol file: 886362-11-4.mol

Synonyms:886362-11-4;Methyl 3',4'-dichloro[1,1'-biphenyl]-4-carboxylate;Methyl 3',4'-dichloro-[1,1'-biphenyl]-4-carboxylate;methyl 4-(3,4-dichlorophenyl)benzoate;DTXSID90594726;MFCD08276964;AKOS005071547;AA-0703;CS-0330590;J-522107;Methyl3',4'-dichloro-[1,1'-biphenyl]-4-carboxylate

Chemical Property of Methyl 3',4'-dichloro[1,1'-biphenyl]-4-carboxylate

Chemical Property:

• Melting Point: 115-117°C
• PSA: 26.30000
• LogP: 4.44700
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 280.0057849
• Heavy Atom Count: 18
• Complexity: 288

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 3',4'-dichloro-[1,1'-biphenyl]-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 3',4'-dichloro[1,1'-biphenyl]-4-carboxylate

There total 4 articles about Methyl 3',4'-dichloro[1,1'-biphenyl]-4-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: 96.0%

4-methoxycarbonylphenyl bromide (619-42-1) + 2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (401797-02-2) → methyl 3',4'-dichlorobiphenyl-4-carboxylate (886362-11-4)

Guidance literature:

With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In hexane; N,N-dimethyl-formamide; at 60 ℃; for 2h;

DOI:10.1016/j.tet.2008.03.102

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) + (3,4-dichloro-phenyl)-trimethyl-stannane → methyl 3',4'-dichlorobiphenyl-4-carboxylate (886362-11-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201304579

Reference yield:

m,p-dichloroaniline (95-76-1) → methyl 3',4'-dichlorobiphenyl-4-carboxylate (886362-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 4 h / 0 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 110 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; toluene; 1: |Sandmeyer Reaction / 2: |Stille Cross Coupling;

DOI:10.1002/anie.201304579

upstream raw materials:

4-methoxycarbonylphenyl bromide

2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

m,p-dichloroaniline

1,2-dichloro-benzene