3-Methylpyridine-2-carboxylic acid Chemical Properties

Melting point:

114-118 °C

Boiling point:

300.6±22.0 °C(Predicted)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

1.11±0.50(Predicted)

form 

Crystalline Powder

color 

White to tan

InChI

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

InChIKey

LMHIBYREWJHKNZ-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=CC=C1C

CAS DataBase Reference

4021-07-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

3-Methylpyridine-2-carboxylic acid Usage And Synthesis

Chemical Properties

White solid

Uses

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

Definition

ChEBI: 3-Methylpicolinic acid is a member of pyridines and an aromatic carboxylic acid.

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.

Synthesis

Synthesis of II-1-2:3-methylpyridine carboxylic acid 2.00 g (19 mmol) of 2-cyano-3-methylpyridine was dissolved in 90% sulfuric acid and the resulting solution was heated and stirred at 120°C for 2 hours. After completion of the reaction, the reaction solution was cooled to 20 °C to 25 °C and a solution of 4.00 g of sodium sulfite dissolved in 8 ml of water was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was continued to be stirred at the same temperature for 1.5 hours, and then warmed up to 75°C-85°C and kept for 1.5 hours. After the reaction solution was cooled, the pH was adjusted to about 3 with sodium carbonate and extracted with chloroform. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1.38 g of solid product. The solid was purified by solvent recrystallization from a mixture of ethyl acetate-hexane to give the final pure product (54.0% yield). The melting point of the product was 115.5°-116.5°C and IR (KBr) showed characteristic absorption peaks: 3350, 1650, 1590 cm-1 .

References

[1] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
[2] Patent: US5219847, 1993, A
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 5967,5969
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1501 - 1505
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 498 - 509

3-Methylpyridine-2-carboxylic acid(4021-07-2)Related Product Information

• 4-(Aminomethyl)benzoic acid
• Quinolinic acid
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Azamethiphos
• p-Toluic acid
• o-Toluic acid
• Stearic acid
• m-Toluic acid
• 4-Methylpyridine
• 2,4,6-Collidine
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 3-Picoline
• 4-(Chloromethyl)benzoic acid
• 2-Picolinic acid
• 2-Chloro-5-chloromethylpyridine
• 2,6-Lutidine
• Citric acid