4-Methylnicotinic acid Chemical Properties

Melting point:

217-221 °C

Boiling point:

304.1±22.0 °C(Predicted)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

1.67±0.25(Predicted)

form 

Crystalline Powder

color 

White to tan

InChI

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

InChIKey

ZKUZSTXNVMIDCY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3222-50-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

4-Methylnicotinic acid Usage And Synthesis

Chemical Properties

White powder

Uses

4-Methylnicotinic Acid is used in the synthesis of nicotinic acid substituted nicotinic acid adenine dinucleotide phosphate analogs.

Synthesis

General procedure for the synthesis of 4-methylpyridine-3-carboxylic acid from 3-cyano-4-methylpyridine: 3-cyano-4-methylpyridine (1.2 kg, 10.2 mol) was added to a mixture of sodium hydroxide (1.6 kg, 40.6 mol) and 70% aqueous ethanol solution (7.2 L). The reaction mixture was stirred under reflux conditions for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and acidified by slow dropwise addition of concentrated hydrochloric acid (4.06 L). Subsequently, the solvent was removed under reduced pressure to give a white solid product. Ethanol (10 L) was added to the residue, heated to reflux and maintained for 10 min. After thermal filtration, ethanol was evaporated under reduced pressure at 20 mmHg to give 4-methylpyridine-3-carboxylic acid as a white solid (1.33 kg, 96% yield). Melting point: 215-216°C (literature value 215-217°C). IR (KBr, cm^-1): 2423 (O-H stretching vibration), 1721 (C=O stretching vibration). 1H NMR (DMSO-d6, 300 MHz): δ 11.9 (broad single peak, 1H, COOH), 9.00 (single peak, 1H, pyridine ring H), 9.00 (single peak, 1H, pyridine ring H). 8.72 (double peak, J = 4.9 Hz, 1H, pyridine ring H), 7.67 (double peak, J = 4.9 Hz, 1H, pyridine ring H), 2.67 (single peak, 3H, CH3).13C NMR (DMSO-d6, 75 MHz): δ 179.7 (COOH), 166.4, 153.9, 148.2, 147.6, 128.3 (pyridine ring C), 21.4 (CH3).MS (ESI): m/z 138.1 [M + H]+, 136.1 [M - H]-.

References

[1] Letters in Organic Chemistry, 2016, vol. 13, # 6, p. 450 - 452
[2] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1456,1458
[4] Journal of the American Chemical Society, 1943, vol. 65, p. 2233,2235
[5] Canadian Journal of Chemistry, 1983, vol. 61, p. 2813 - 2820

4-Methylnicotinic acid(3222-50-2)Related Product Information

• 4-Methylnicotinic acid
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• PYRIDINE-3,4-DICARBOXYLIC ANHYDRIDE
• 4-(Trifluoromethyl)nicotinic acid
• ETHYL 2,4-DIMETHYLPYRIDINE-3-CARBOXYLATE
• 4-(METHOXYCARBONYL)NICOTINIC ACID
• DIETHYL 3 4-PYRIDINEDICARBOXYLATE 97
• 4-(TRIFLUOROMETHYL)PYRIDINE-2-CARBOXYLIC ACID
• 2-HYDROXY-6-METHYLISONICOTINIC ACID
• 2-Chloro-6-methylpyridine-4-carboxylic acid
• 2-METHYLNICOTINIC ACID
• 4-METHYL-PYRIDINE-2-CARBOXYLIC ACID
• 5-METHYLNICOTINIC ACID
• 6-METHYLNICOTINIC ACID METHYL ESTER
• Imazamox
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• N-METHYLNICOTINIC ACID AMIDE CHLORIDE SALT,n-methylnicotinic acid amide chloride
• Pyrazosulfuron-ethyl