pyridine-2-carboxylic acid

• ChemBase ID: 70264
• Molecular Formular: C6H5NO2
• Molecular Mass: 123.1094
• Monoisotopic Mass: 123.03202841
• SMILES: c1(ccccn1)C(=O)O
• Canonical SMILES: OC(=O)c1ccccn1
• InChI: InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
• InChIKey: SIOXPEMLGUPBBT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine-2-carboxylic acid
• IUPAC Traditional name: picolinate; picolinic acid
• Synonyms: 2-Picolinic acid; Pyridine-2-carboxylic acid; 2-pyridinecarboxylic acid; 2-Picolinic acid; α-Picolinic acid; Pyridine-2-carboxylic acid; 2-Pyridinecarboxylic Acid; 2-Carboxypyridine; 2-Pyridylcarboxylic Acid; NSC 171; PCL 016; o-Pyridinecarboxylic Acid; α-Pyridinecarboxylic Acid; Picolinic acid; 皮考林酸; 2-吡啶甲酸; 吡啶-2-羧酸; 吡啶2-甲酸

Database IDs

• CAS Number: 4930-98-7; 98-98-6
• EC Number: 202-719-7
• MDL Number: MFCD00006293
• Beilstein Number: 109595
• Merck Index: 147403
• PubChem SID: 24864454; 24898523; 24887354; 162035987
• PubChem CID: 1018
• CHEBI ID: 28747
• CHEMBL: 72628
• Chemspider ID: 993
• Wikipedia Title: Picolinic_acid

CALCULATED PROPERTIES

• Acid pKa: 0.99192774
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.95603275
• LogD (pH = 7.4): -2.3328586
• Log P: -0.6724588
• Molar Refractivity: 30.7853 cm^3
• Polarizability: 11.798748 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless to almost colorless; H2O: soluble50 mg/mL, clear
• Apperance: White to tan crystalline solid
• Melting Point: 135-137 °C; 135-139°C; 136-138 °C; 136-140 °C; 139-142 °C(lit.); 139-142°C
• Flash Point: 139°C(232°F)

Safety Information

• Storage Warning: Harmful/Irritant/Store under Argon; IRRITANT
• RTECS: TJ7344000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36; 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H319
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99.5% (HPLC); 95+%; 97%; 98%; 99%
• Grade: matrix substance for MALDI-MS; purum; ReagentPlus®
• Cation Traces: Ba: <5 mg/kg; Ca: <5 mg/kg; Cd: <5 mg/kg; Co: <5 mg/kg; Cr: <5 mg/kg; Cu: <5 mg/kg; K: <5 mg/kg; Mg: <5 mg/kg; Mn: <5 mg/kg; Na: <15 mg/kg; Ni: <5 mg/kg; Pb: <5 mg/kg; Zn: <5 mg/kg
• Analyte suitability: oligonucleotides; proteins
• abs.: absorption/264 nm ≥3000 (mol. absorption)
• Empirical Formula (Hill Notation): C6H5NO2

DETAILS

Sigma Aldrich - P42800

Packaging
100, 500 g in poly bottle
2 kg in poly bottle
5 g in glass bottle
Application
Chelate for alkaline earth metals.1 Used to prepare picolinato ligated transition metal complexes.2,3,4
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P437220

Used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.

REFERENCES

• Denny, W., et al.: J. Med. Chem., 33, 814 (1990)
• Maurya, M., et al.: J. Chem. Res., 446 (1990)
• Amino groups can be protected, by DCC coupling, as picolinamides, which can be cleaved with acidic Cu(OAc)₂: Synth. Commun., 383 (1972).
• Has been found to accelerate significantly oxidations with chromic acid: J. Am. Chem. Soc., 98, 1026 (1976).