3'-Cyano-[1,1'-biphenyl]-3-carboxylic acid

Base Information

• Chemical Name: 3'-Cyano-[1,1'-biphenyl]-3-carboxylic acid
• CAS No.: 253678-93-2
• Molecular Formula: C14H9 N O2
• Molecular Weight: 223.231
• European Community (EC) Number: 673-759-4
• DSSTox Substance ID: DTXSID30948209
• Wikidata: Q82925986
• ChEMBL ID: CHEMBL2089277
• Mol file: 253678-93-2.mol

Synonyms:3'-Cyano-[1,1'-biphenyl]-3-carboxylic acid;253878-93-2;3'-cyanobiphenyl-3-carboxylic acid;253678-93-2;3-(3-cyanophenyl)benzoic Acid;3'-Cyano-biphenyl-3-carboxylic acid;3'-cyano[1,1'-biphenyl]-3-carboxylic acid;SCHEMBL5529069;CHEMBL2089277;DTXSID30948209;MFCD04117360;AKOS004117518;BS-24888;3-Chloro-N-[(phenylthio)methyl]benzenamine;BB 0223039;CS-0207350;3'-Cyano-[1,1'-biphenyl]-3-carboxylicacid;J-015976

Chemical Property of 3'-Cyano-[1,1'-biphenyl]-3-carboxylic acid

Chemical Property:

• Boiling Point: 456.4±38.0 °C(Predicted)
• PKA: 4.02±0.10(Predicted)
• PSA: 61.09000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 2.92348
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 223.063328530
• Heavy Atom Count: 17
• Complexity: 330

Purity/Quality:

99%min ^*data from raw suppliers

3'-Cyano-[1,1'-biphenyl]-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3'-Cyano-[1,1'-biphenyl]-3-carboxylic acid

There total 3 articles about 3'-Cyano-[1,1'-biphenyl]-3-carboxylic 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: 88.0%

3'-cyanobiphenyl-3-carboxylic acid ethyl ester (1072438-69-7) → 3'-cyanobiphenyl-3-carboxylic acid (253678-93-2)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 18h;

Reference yield: 53.0%

m-bromobenzoic acid (585-76-2) + (3‐cyanophenyl)boronic acid (150255-96-2) → 3'-cyanobiphenyl-3-carboxylic acid (253678-93-2)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ml3000935

Reference yield:

3-iodobenzoic acid methyl ester (58313-23-8) + (3‐cyanophenyl)boronic acid (150255-96-2) → 3'-cyanobiphenyl-3-carboxylic acid (253678-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; sodium carbonate / water; N,N-dimethyl-formamide / 48 h / 110 °C

2: lithium hydroxide monohydrate / water; tetrahydrofuran / 18 h / 20 °C

With lithium hydroxide monohydrate; palladium diacetate; sodium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1: |Suzuki Coupling;

upstream raw materials:

m-bromobenzoic acid

(3‐cyanophenyl)boronic acid

3-iodobenzoic acid methyl ester

3'-cyanobiphenyl-3-carboxylic acid ethyl ester

Downstream raw materials:

N-[(4-carbamimidoylphenyl)methyl]-3-(3-cyanophenyl)benzamide hydrochloride

Refernces

• 1、 -. "RECEPTOR ANTAGONISTS". . . Retrieved 2014/02/16.