4-Methylnicotinic acid

Base Information

• Chemical Name: 4-Methylnicotinic acid
• CAS No.: 3222-50-2
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 29333990
• European Community (EC) Number: 625-824-3
• NSC Number: 22592
• DSSTox Substance ID: DTXSID40281715
• Nikkaji Number: J706.881F
• Wikidata: Q72493339
• ChEMBL ID: CHEMBL1551493
• Mol file: 3222-50-2.mol

Synonyms:4-Methylnicotinic acid;3222-50-2;4-Methylpyridine-3-carboxylic acid;4-Methyl-3-pyridinecarboxylic acid;3-Pyridinecarboxylic acid, 4-methyl-;MFCD00128869;4-methylnicotinicacid;NSC22592;4-Methyl-nicotinic acid;SCHEMBL258230;CHEMBL1551493;DTXSID40281715;BCP26754;3-Pyridinecarboxylic acid,4-methyl-;NSC 22592;NSC-22592;STK693803;AKOS000271608;AC-2931;CS-W002396;PB17119;SB10537;NCGC00166267-01;NCGC00166267-02;SY003372;TS-01767;4-Methylpyridine-3-carboxylic acid, 97%;A5793;AM20051066;FT-0600278;EN300-84041;AB00443361-03;J-018682;J-515816;F1957-0023;Z199468010;4-methylnicotinic acid

Chemical Property of 4-Methylnicotinic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 217-221 °C
• Refractive Index: 1.561
• Boiling Point: 304.094 °C at 760 mmHg
• PKA: 1.67±0.25(Predicted)
• Flash Point: 137.712 °C
• PSA: 50.19000
• Density: 1.23 g/cm³
• LogP: 1.08820
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-MethylnicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=NC=C1)C(=O)O
• Uses: 4-Methylnicotinic Acid is used in the synthesis of nicotinic acid substituted nicotinic acid adenine dinucleotide phosphate analogs.

Technology Process of 4-Methylnicotinic acid

There total 8 articles about 4-Methylnicotinic 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: 96.0%

3-cyano-4-methylpyridine (5444-01-9) → 4-methylnicotinic acid (3222-50-2)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 2h; Reflux; Large scale;

DOI:10.2174/1570178613666160728154935

Reference yield: 58.4%

4-methylnicotinic acid methyl ester (33402-75-4) → 4-methylnicotinic acid (3222-50-2)

Guidance literature:

4-methylnicotinic acid methyl ester; With water; sodium hydroxide; In 1,4-dioxane; at 50 - 60 ℃; for 1h;

With hydrogenchloride; In water; pH=~ 6;

Reference yield:

3-Bromo-4-methylpyridin (3430-22-6) → 4-methylnicotinic acid (3222-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 10 h / 70 - 80 °C / 2585.81 Torr

2.1: sodium hydroxide; water / 1,4-dioxane / 1 h / 50 - 60 °C

2.2: pH ~ 6

With water; triethylamine; sodium hydroxide; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

3-ethyl-4-methylpyridine

3-cyano-4-methylpyridine

4-methyl-2,3-pyridinedicarboxylic acid

4-methylnicotinic acid methyl ester

Downstream raw materials:

4-methylnicotinic acid ethyl ester

4-methylnicotinoyl chloride

4-phenacyl-nicotinic acid

4-(chloromethyl)nicotinoyl chloride

Refernces

• 1、 Yu, Zhaoxue,Sha, Fei,Wang, Peng. "Practical and efficient large-scale preparation of 4-methylnicotinic acid". . p. 450 - 452. Retrieved 2016/10/18.
• 2、 -. "Azaisoquinolinone derivatives as NK3 antagonists". Paragraph 0147. . Retrieved 2013/07/31.