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

Base Information

• Chemical Name: Methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate
• CAS No.: 89900-94-7
• Molecular Formula: C15H14O2
• Molecular Weight: 226.275
• Hs Code.: 2902900000
• DSSTox Substance ID: DTXSID50362665
• Wikidata: Q72488240
• Mol file: 89900-94-7.mol

Synonyms:89900-94-7;Methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate;Methyl 4-(3-methylphenyl)benzoate;3'-Methyl-[1,1'-biphenyl]-4-carboxylic acid methyl ester;SCHEMBL6138470;DTXSID50362665;MFCD05981314;AKOS002678682;AS-3254;BB 0222623;CS-0189011;FT-0749100;methyl 3'-methyl[1,1'-biphenyl]-4-carboxylate;Methyl3'-methyl-[1,1'-biphenyl]-4-carboxylate;3'-Methyl-biphenyl-4-carboxylic acid methyl ester

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

Chemical Property:

• Melting Point: 58-59 °C
• Boiling Point: 345.2 °C at 760 mmHg
• Flash Point: 155 °C
• Density: 1.083 g/cm³
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 226.099379685
• Heavy Atom Count: 17
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

Methyl3’-Methyl-[1,1’-biphenyl]-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C2=CC=C(C=C2)C(=O)OC

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

There total 4 articles about Methyl 3'-methyl-[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: 78.0%

m-tolylboronic acid (17933-03-8) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate (89900-94-7)

Guidance literature:

4-methoxycarbonylphenylboronic acid; With iodine; potassium carbonate; In acetonitrile; at 80 ℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;

m-tolylboronic acid; With palladium diacetate; In acetonitrile; at 80 ℃; for 14h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1055/s-0033-1340871

Reference yield: 30.0%

methyl 4-iodobenzoate (619-44-3) + toluene (108-88-3,15644-74-3,16713-13-6) → methyl 4-(4-tolyl)benzoate (49742-56-5) + methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate (89900-94-7) + 4-methyloxycarbonyl-2'-methyl-1,1'-biphenyl (89900-99-2)

Guidance literature:

With tris(4-anisyl)amine; 2-butyl-4,7-bis(1-methyl-1H-pyrrol-2-yl)-2H-benzo[d][1,2,3]triazole; In dimethyl sulfoxide; at 20 ℃; for 24h; Irradiation; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201800950

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) + methyl 4-formylbenzoate (1571-08-0) → methyl 4-(4-tolyl)benzoate (49742-56-5) + methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate (89900-94-7) + 4-methyloxycarbonyl-2'-methyl-1,1'-biphenyl (89900-99-2)

Guidance literature:

With di-tert-butyl peroxide; 1,2-Dinitrobenzene; at 150 ℃; for 12h; Overall yield = 54 %; Overall yield = 24.4 mg; Inert atmosphere; Sealed tube;

DOI:10.1039/c4cc10155c

upstream raw materials:

methanol

m-tolylboronic acid

4-methoxycarbonylphenylboronic acid

toluene

Downstream raw materials:

3'‐methyl‐(1,1'‐biphenyl)‐4‐carboxylic acid

Refernces

• 1、 Tang, Ren-Jin,He, Qing,Yang, Luo. "Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: Direct access to biaryls". supporting information. p. 5925 - 5928. Retrieved 2015/03/30.
• 2、 -. "Use of functionalized onium salts as a soluble support for organic synthesis". Page/Page column 51. . Retrieved 2010/11/25.