Picolinic acid

Base Information

• Chemical Name: Picolinic acid
• CAS No.: 98-98-6
• Deprecated CAS: 1580002-25-0,2244586-27-2
• Molecular Formula: C6H5NO2
• Molecular Weight: 123.111
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE
• European Community (EC) Number: 202-719-7
• NSC Number: 171
• UNII: QZV2W997JQ
• DSSTox Substance ID: DTXSID7031903
• Nikkaji Number: J45.682I
• Wikipedia: Picolinic acid
• Wikidata: Q416682
• Pharos Ligand ID: KZ5DFKLARK4B
• Metabolomics Workbench ID: 38092
• ChEMBL ID: CHEMBL72628
• Mol file: 98-98-6.mol

Synonyms:2-pyridine carboxylic acid;2-pyridinecarboxylic acid;calcium dipicolinate trihydrate;chromium picolinate;iron(III) picolinate;picolinate;picolinic acid;picolinic acid, hydrochloride;picolinic acid, sodium salt;pyridine-2-carboxylic acid;zinc picolinate

Chemical Property of Picolinic acid

Chemical Property:

• Appearance/Colour: Off-white to tan powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 139-142 °C(lit.)
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 292.467 °C at 760 mmHg
• PKA: 1.07(at 25℃)
• Flash Point: 130.68 °C
• PSA: 50.19000
• Density: 1.293 g/cm³
• LogP: 0.77980
• Storage Temp.: Store at RT.
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: 887 g/L (20 ºC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 123.032028402
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

99% Min ^*data from raw suppliers

2-Pyridinecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26-36-33-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)C(=O)O
• Uses: 2-Picolinic acid is used as a chelate for alkaline earth metals. It is also used to prepare picolinato ligated transition metal complexes. In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.

Technology Process of Picolinic acid

There total 178 articles about Picolinic 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: 95.0%

indolin-1-yl(pyridin-2-yl)methanone (864424-24-8) → 2-Picolinic acid (98-98-6) + 1-indoline (496-15-1)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 4h;

DOI:10.1039/c3sc51211h

Reference yield: 84.0%

C16H17NO2 (1309453-54-0) → 2-Picolinic acid (98-98-6) + C16H15NO2 (338415-92-2) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

C₁₆H₁₇NO₂; With oxygen; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 6h;

With hydrogenchloride; In water;

DOI:10.1016/j.tet.2011.03.052

Reference yield: 50.0%

α-picoline (109-06-8) + 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide (2196-95-4,17213-48-8) → pyridine (110-86-1) + pyridine-2-carbaldehyde (1121-60-4) + 2-Picolinic acid (98-98-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,1'-dihydroxy-2,2'-diphenyl-3,3'-biindole (5169-64-2) + 2,2'-diphenyl-1H,1'H-3,3'-biindole (2415-33-0)

Guidance literature:

at 140 ℃; for 14h; Product distribution;

DOI:10.1007/BF00808311

upstream raw materials:

α-picoline

pyridine-2-carbaldehyde

2-bromo-pyridine

2-Cyanopyridine

Downstream raw materials:

methyl pyridine-2-carboxylate

diphenyl(2-pyridyl)methanol

octyl 2-pyridinecarboxylate

ethyl-2-picolinate

Refernces

• 1、 Jursic, Branko S,Neumann, Donna M,Martin, Kenneth L,Stevens, Edwin D. "Barbituric acid initiated rearrangement of 2,2'-pyridil into 5,5'-(2-pyrilidine)bisbarbituric acid.". . p. 811 - 813. Retrieved 2002.
• 2、 Eberle, S. H.,Robel, W.. "". . p. 359. Retrieved 1970.
• 3、 Brunner, Jens,Mokhir, Andriy,Kraemer, Roland. "DNA-templated metal catalysis". . p. 12410 - 12411. Retrieved 2003.
• 4、 Li, Tingfeng,Ma, John K.,Hosler, Jonathan P.,Davidson, Victor L.,Liu, Aimin. "Detection of transient intermediates in the metal-dependent nonoxidative decarboxylation catalyzed by α-amino-β-carboxymuconate-ε- semialdehyde decarboxylase". . p. 9278 - 9279. Retrieved 2007.
• 5、 Sen, Bhaskar,Sheet, Sanjoy Kumar,Patra, Sumit Kumar,Koner, Debaprasad,Saha, Nirmalendu,Khatua, Snehadrinarayan. "Highly Selective Detection of Hypochlorous Acid by a Bis-heteroleptic Ru(II) Complex of Pyridyl-1,2,3-triazole Ligand via C(sp2)-H Hydroxylation". . p. 9982 - 9991. Retrieved 2019.
• 6、 Yokoyama. "-". . p. 69. Retrieved 1932.
• 7、 Du, Nana,Gong, Lige,Wang, Chunmei,Wang, Chunxiao,Yu, Kai,Zhang, Wenjia,Zhou, Baibin. "{BW12O40} Hybrids Modified by in Situ Synthesized Rigid Ligand with Supercapacitance and Photocatalytic Properties". supporting information. p. 16357 - 16369. Retrieved 2021/11/13.
• 8、 Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan. "Selective oxidation of alkenes to carbonyls under mild conditions". supporting information. p. 5549 - 5555. Retrieved 2021/08/16.