5-(4-Formylphenyl)nicotinic acid

Base Information

• Chemical Name: 5-(4-Formylphenyl)nicotinic acid
• CAS No.: 566198-28-5
• Molecular Formula: C₁₃H₉NO₃
• Molecular Weight: 227.219
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID80383262
• Nikkaji Number: J1.905.579E
• Wikidata: Q82174926
• Mol file: 566198-28-5.mol

Synonyms:5-(4-Formylphenyl)nicotinic acid;566198-28-5;5-(4-formylphenyl)pyridine-3-carboxylic Acid;3-Pyridinecarboxylic acid, 5-(4-formylphenyl)-;MFCD05664413;SCHEMBL15330383;DTXSID80383262;AMY20360;AKOS004118679;SB55156;NCGC00374189-01;AS-37803;SY017024;BB 0223904;CS-0170950;A869882

Chemical Property of 5-(4-Formylphenyl)nicotinic acid

Chemical Property:

• Vapor Pressure: 3.06E-10mmHg at 25°C
• Melting Point: 231 °C
• Refractive Index: 1.647
• Boiling Point: 485.5 °C at 760 mmHg
• Flash Point: 247.4 °C
• PSA: 67.26000
• Density: 1.319 g/cm³
• LogP: 2.25930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 227.058243149
• Heavy Atom Count: 17
• Complexity: 284

Purity/Quality:

98%min ^*data from raw suppliers

5-(4-Formylphenyl)nicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=O)C2=CC(=CN=C2)C(=O)O
• Uses: 5-(4-Formylphenyl)nicotinic Acid is a derivative of Nicotinic Acid (N429250), a precursor of the coenzymes NAD and NADP. Widely distributed in nature; appreciable amounts are found in liver , fish, yeast and cereal grains. Dietary deficiency is associated with pellagra. The term “niacin” has also been applied to nicotinamide or to other derivatives exhibiting the biological activity of nicotinic acid. Vitamin (enzyme cofactor).

Technology Process of 5-(4-Formylphenyl)nicotinic acid

There total 2 articles about 5-(4-Formylphenyl)nicotinic 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: 78.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + 4-formylphenylboronic acid, (87199-17-5) → 5-(4-formylphenyl)-nicotinic acid (566198-28-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Davisil 500 Angstroem beads; sodium carbonate; In water; for 48h; Heating;

DOI:10.1016/S0040-4039(03)01128-6

Reference yield:

5-bromo-3-picoline (3430-16-8) → 5-(4-formylphenyl)-nicotinic acid (566198-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. KMnO₄ / Heating

2.1: [Pd(PPh₃)4] / 1,2-dimethoxy-ethane

2.2: 69 percent / aq. Na₂CO₃ / Heating

With potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; 2.2: Suzuki-Miyaura coupling reaction;

upstream raw materials:

5-bromo-3-pyridinecarboxylic acid

4-formylphenylboronic acid,

5-bromo-3-picoline

Refernces

• 1、 Meier, Peter,Legraverant, Stephanie,Mueller, Sascha,Schaub, Josette. "Synthesis of formylphenylpyridinecarboxylic acids using Suzuki-Miyaura coupling reactions". . p. 551 - 554. Retrieved 2007/10/03.