2-Phenylisonicotinic acid

Base Information

• Chemical Name: 2-Phenylisonicotinic acid
• CAS No.: 55240-51-2
• Molecular Formula: C12H9NO2
• Molecular Weight: 199.209
• Hs Code.: 2933399090
• European Community (EC) Number: 692-864-6
• DSSTox Substance ID: DTXSID50376505
• Nikkaji Number: J2.780.037H
• Wikidata: Q82165412
• Mol file: 55240-51-2.mol

Synonyms:2-Phenylisonicotinic acid;55240-51-2;2-phenylpyridine-4-carboxylic Acid;4-Pyridinecarboxylic acid, 2-phenyl-;2-Phenyl-4-pyridinecarboxylic acid;MFCD03086008;2-PhenylisonicotinicAcid;2-phenyl-isonicotinic acid;2-(Phenyl)-isonicotinic acid;2-PHENYL-ISONICOTINICACID;4-Carboxy-2-phenylpyridine;SCHEMBL648273;DTXSID50376505;OMMKWOVBOKXXQU-UHFFFAOYSA-N;AKOS004911929;CCG-139870;PS-4415;SY028466;FT-0763372;P2453;E10166;EN300-6492941;Z2905488608

Chemical Property of 2-Phenylisonicotinic acid

Chemical Property:

• Vapor Pressure: 5.6E-10mmHg at 25°C
• Melting Point: 270-271 °C
• Refractive Index: 1.613
• Boiling Point: 478.8 °C at 760 mmHg
• PKA: 1.89±0.10(Predicted)
• Flash Point: 243.4 °C
• PSA: 50.19000
• Density: 1.241g/cm³
• LogP: 2.44680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 199.063328530
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

98%min ^*data from raw suppliers

2-Phenylisonicotinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Phenylisonicotinic acid

There total 8 articles about 2-Phenylisonicotinic 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: 91.0%

2-bromoisonicotinic acid (66572-56-3) + phenylboronic acid (98-80-6) → 2-phenylpyridine-4-carboxylic acid (55240-51-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; water; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.6b03085

Reference yield: 84.0%

4-methyl-2-phenylpyridine (3475-21-6) → 2-phenylpyridine-4-carboxylic acid (55240-51-2)

Guidance literature:

With selenium(IV) oxide; In pyridine; Heating / reflux;

Reference yield:

2-phenylisonicotinic acid methyl ester (4634-14-4) → 2-phenylpyridine-4-carboxylic acid (55240-51-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01169

upstream raw materials:

4-methyl-2-phenylpyridine

2-bromoisonicotinic acid

phenylboronic acid

2-phenylisonicotinic acid methyl ester

Downstream raw materials:

2-phenylisonicotinic acid methyl ester

2-phenylisonicotinohydrazide

4-(hydroxymethyl)-2-phenylpyridine

C₂₀H₁₇N₃O₂S

Refernces

• 1、 Leaver, David J.,Cleary, Benjamin,Nguyen, Nghi,Priebbenow, Daniel L.,Lagiakos, H. Rachel,Sanchez, Julie,Xue, Lian,Huang, Fei,Sun, Yuxin,Mujumdar, Prashant,Mudududdla, Ramesh,Varghese, Swapna,Teguh, Silvia,Charman, Susan A.,White, Karen L.,Katneni, Kasiram,Cuellar, Matthew,Strasser, Jessica M.,Dahlin, Jayme L.,Walters, Michael A.,Street, Ian P.,Monahan, Brendon J.,Jarman, Kate E.,Sabroux, Helene Jousset,Falk, Hendrik,Chung, Matthew C.,Hermans, Stefan J.,Parker, Michael W.,Thomas, Tim,Baell, Jonathan B.. "Discovery of benzoylsulfonohydrazides as potent inhibitors of the histone acetyltransferase KAT6A". . p. 7146 - 7159. Retrieved 2019/08/28.
• 2、 Johnston, Adam J. S.,Ling, Kenneth B.,Sale, David,Lebrasseur, Nathalie,Larrosa, Igor. "Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen". supporting information. p. 6094 - 6097. Retrieved 2016/12/09.