75754-04-0

Basic information

• Product Name: 5-PHENYLPICOLINIC ACID
• Synonyms: 5-PHENYLPICOLINIC ACID;5-PHENYLPYRIDINE-2-CARBOXYLIC ACID;5-(2-Methoxyphenyl)-picolinic acid;5-(2-Methylphenyl)-picolinic acid;5-(3-Methoxyphenyl)-picolinic acid;5-(3-Methylphenyl)-picolinic acid;5-(4-Ethylphenyl)-picolinic acid;5-(4-Methylphenyl)-picolinic acid
• CAS NO: 75754-04-0
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• Mol File: 75754-04-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 156-157℃
• Boiling Point: 399℃
• Flash Point: 195℃
• Appearance: /
• Density: 1.241
• Vapor Pressure: 4.48E-07mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-PHENYLPICOLINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYLPICOLINIC ACID(75754-04-0)
• EPA Substance Registry System: 5-PHENYLPICOLINIC ACID(75754-04-0)

Safety Data

• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 75754-04-0(Hazardous Substances Data)

Usage

General Description

5-Phenylpicolinic acid is a chemical compound with the molecular formula C12H9NO2. It is a derivative of picolinic acid, consisting of a phenyl group attached to the pyridine ring. 5-PHENYLPICOLINIC ACID is commonly used as a chelating agent in coordination chemistry and as a precursor in the synthesis of metal complexes. It has also been studied for its potential pharmaceutical applications, particularly in the development of drugs for neurological disorders and cancer. Additionally, 5-phenylpicolinic acid has been investigated for its antioxidant and anti-inflammatory properties, which could make it a promising candidate for various medical and industrial applications.

InChI:InChI=1/C12H9NO2/c14-12(15)11-7-6-10(8-13-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 98-80-6 phenylboronic acid 
• 29682-15-3 methyl 5-bromopicolinate 
• 7540-67-2 O-acetyl-L-homoserine 
• 122-78-1 phenylacetaldehyde 
• 39065-45-7 2-cyano-5-phenylpyridine 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 65117-74-0 ethyl 5-phenylpicolinate 
• 624-28-2 2,5-dibromopyridine 
• 77199-09-8 5-bromo-pyridine-2-carboxylic acid ethyl ester 
• 30766-11-1 5-bromoisonicotinic acid 
• 86574-52-9 methyl 5-phenylpyridine-2-carboxylate 
• 3256-88-0 5-phenyl-2-picoline 
• 7089-34-1 ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 

Downstream Products

• 150461-41-9 5-phenylpicolinoyl chloride 
• 1008-88-4 3-phenylpyridine 
• 99602-91-2 C₁₈H₁₂N₂ 
• 86574-52-9 methyl 5-phenylpyridine-2-carboxylate 
• 780800-85-3 5-phenylpyridine-2-carboxaldehyde 
• 107351-82-6 2-bromo-5-phenyl-pyridine 
• 66600-05-3 2-chloro-5-phenylpyridine 

Relevant articles and documents

Biosynthesis of Mycotoxin Fusaric Acid and Application of a PLP-Dependent Enzyme for Chemoenzymatic Synthesis of Substituted l -Pipecolic Acids

Fusaric acid (FA) is a well-known mycotoxin that plays an important role in plant pathology. The biosynthetic gene cluster for FA has been identified, but the biosynthetic pathway remains unclarified. Here, we elucidated the biosynthesis of FA, which features a two-enzyme catalytic cascade, a pyridoxal 5′-phosphate (PLP)-dependent enzyme (Fub7), and a flavin mononucleotide (FMN)-dependent oxidase (Fub9) in synthesizing the picolinic acid scaffold. FA biosynthesis also involves an off-line collaboration between a highly reducing polyketide synthase (HRPKS, Fub1) and a nonribosomal peptide synthetase (NRPS)-like carboxylic acid reductase (Fub8) in making an aliphatic α,β-unsaturated aldehyde. By harnessing the stereoselective C-C bond-forming activity of Fub7, we established a chemoenzymatic route for stereoconvergent synthesis of a series of 5-alkyl-, 5,5-dialkyl-, and 5,5,6-trialkyl-l-pipecolic acids of high diastereomeric ratio.

Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.

Fusaric acid and analogues as Gram-negative bacterial quorum sensing inhibitors

Taking advantage of microwave-assisted synthesis, efficient and expedite procedures for preparation of a library of fusaric acid and 39 analogues are reported. The fusaric acid analogues were tested in cell-based screening assays for inhibition of the las and rhl quorum sensing system in Pseudomonas aeruginosa and the lux quorum sensing system in Vibrio fischeri. Eight of the 40 compounds in the library including fusaric acid inhibited lux quorum sensing and one compound inhibited activity of the las quorum sensing system. To our delight, none of the compounds showed growth inhibitory effects in the tested concentration ranges.