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Sigma-Aldrich

3-Methylpyridine-2-carboxylic acid

97%

Synonym(s):

3-Methylpicolinic acid

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About This Item

Empirical Formula (Hill Notation):
C7H7NO2
CAS Number:
4021-07-2
Molecular Weight:
137.14
MDL number:
MFCD00191553
UNSPSC Code:
12352100
PubChem Substance ID:
24873626
NACRES:
NA.22

Assay

97%

form

solid

mp

114-118 °C

SMILES string

Cc1cccnc1C(O)=O

InChI

1S/C7H7NO2/c1-5-3-2-4-8-6(5)7(9)10/h2-4H,1H3,(H,9,10)

InChI key

LMHIBYREWJHKNZ-UHFFFAOYSA-N

Related Categories

General description

3-Methylpyridine-2-carboxylic acid, also known as 3-methylpicolinic acid (3-MepicH), is a 3-substituted picolinic acid. The dianion formed by reacting 3-MepicH with lithium diisopropylamide (LDA) can undergo C-alkylation with 3-chlorobenzyl chloride.

Application

3-Methylpyridine-2-carboxylic acid (3-MepicH) may be used as a ligand in the synthesis of the following metal complexes:
  • [Cu(3-Mepic)2(4-pic)] where 4-pic=4-picoline and [Cu(3-Mepic)2]·2H2O
  • [Co(3-Mepic)3]
  • [Ni(3-Mepic)2(H2O)2]
  • bis(3-methyl-picolinato-κ2 N,O)(1,10-phenanthroline)zinc(II) tetrahydrate

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ozonolysis of some 8-alkoxyquinolines, and synthesis of a precursor to the non-sedating antihistamine Claritin.
Eichler MC and Grayson DH.
ARKIVOC (Gainesville, FL, United States), 6, 38-53 (2014)
Synthesis and characterization of copper (II) complexes with 3-methylpicolinic acid. Crystal and molecular structure of bis (3-methylpicolinato-N,O)(4-picoline) copper (II).
Kukovec BM, et al.
Journal of Coordination Chemistry, 61(19), 3092-3101 (2008)
Hoi-Ling Seng et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 23(1), 99-118 (2009-09-30)
Crystal structure analysis of the zinc complex establishes it as a distorted octahedral complex, bis(3-methylpicolinato-kappa(2) N,O)(2)(1,10-phenanthroline-kappa(2) N,N)-zinc(II) pentahydrate, [Zn(3-Me-pic)(2)(phen)]x5H(2)O. The trans-configuration of carbonyl oxygen atoms of the carboxylate moieties and orientation of the two planar picolinate ligands above and before
Synthesis, structural, spectroscopic and thermal characterization of cobalt complexes with 3-and 6-methylpicolinic acid. Voltammetric and spectrophotometric study in solution.
Kukovec BM, et al.
Inorgorganica Chimica Acta, 362(8), 2704-2714 (2009)
Synthesis, X-ray structural, IR spectroscopic, thermal and DFT studies of nickel (II) and copper (II) complexes with 3-methylpicolinic acid. UV-Vis spectrophotometric study of complexation in the solution.
Kukovec BM, et al.
Polyhedron, 52, 1349-1361 (2013)
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