2'-AMINO-BIPHENYL-3-CARBOXYLIC ACID METHYL ESTER

Base Information

• Chemical Name: 2'-AMINO-BIPHENYL-3-CARBOXYLIC ACID METHYL ESTER
• CAS No.: 177171-13-0
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.263
• Hs Code.: 2922499990
• Mol file: 177171-13-0.mol

Synonyms:2'-Aminobiphenyl-3-carboxylicacid methyl ester;

Chemical Property of 2'-AMINO-BIPHENYL-3-CARBOXYLIC ACID METHYL ESTER

Chemical Property:

• Boiling Point: 390.7 °C at 760 mmHg
• Flash Point: 226.3 °C
• PSA: 52.32000
• Density: 1.166 g/cm³
• LogP: 3.30360
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Methyl2''-Amino-[1,1''-biphenyl]-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-AMINO-BIPHENYL-3-CARBOXYLIC ACID METHYL ESTER

There total 7 articles about 2'-AMINO-BIPHENYL-3-CARBOXYLIC ACID 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: 100.0%

methanol (67-56-1) + 2-amino-3'-biphenylcarboxylic acid (177171-15-2) → methyl 2-amino-3'-biphenylcarboxylate (177171-13-0)

Guidance literature:

With thionyl chloride; for 100h; Heating;

DOI:10.1021/jo952194k

Reference yield:

2-iodophenylamine (615-43-0) + [3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4) → methyl 2-amino-3'-biphenylcarboxylate (177171-13-0)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate; In 1,4-dioxane; water; at 65 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00690

Reference yield:

3-bromobenzoyl chloride (1711-09-7) → methyl 2-amino-3'-biphenylcarboxylate (177171-13-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 1.) s-BuLi, 2.) B(OMe)3, 3.) Pd(PPh₃)4, aq. Na₂CO₃ / 1) THF, -95 deg C, 10 min; 2) THF, -80 deg C, 2 h, -20 --> -10 deg C, overnight, rt, 1 h; 3) DME, reflux, 50 h

3: 95 percent / NaOH / methanol / 6 h / Heating

4: 1.) Et₃N, diphenyl phosphorazidate, 2.) conc. HCl, phenol / 1) reflux, 22.5 h; 2) 110 deg C, 45 h

5: 100 percent / thionyl chloride / 100 h / Heating

With hydrogenchloride; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; Trimethyl borate; diphenyl phosphoryl azide; sec.-butyllithium; sodium carbonate; triethylamine; phenol; In methanol; dichloromethane;

DOI:10.1021/jo952194k

upstream raw materials:

methanol

2-amino-3'-biphenylcarboxylic acid

3-bromobenzoyl chloride

3-bromo-N-tert-butyl-N-methylbenzamide

Downstream raw materials:

2'-Phenylacetylamino-biphenyl-3-carboxylic acid methyl ester

2-(benzylamido)-3'-biphenylcarboxylic acid

Refernces

• 1、 Ling, Peng-Xiang,Chen, Kai,Shi, Bing-Feng. "Palladium-catalyzed interannular meta-C-H arylation". supporting information. p. 2166 - 2169. Retrieved 2017/02/19.