4-Chloronicotinic acid

Base Information

• Chemical Name: 4-Chloronicotinic acid
• CAS No.: 10177-29-4
• Molecular Formula: C6H4ClNO2
• Molecular Weight: 157.556
• Hs Code.: 29333990
• European Community (EC) Number: 628-434-1
• DSSTox Substance ID: DTXSID00355921
• Nikkaji Number: J1.252.678D
• Wikidata: Q72455622
• Mol file: 10177-29-4.mol

Synonyms:4-Chloronicotinic acid;10177-29-4;4-Chloropyridine-3-carboxylic acid;4-Chloro-3-pyridinecarboxylic acid;4-Chloronicotinicacid;3-PYRIDINECARBOXYLIC ACID, 4-CHLORO-;MFCD00128860;4-chloro-nicotinic acid;SCHEMBL7533;AF-399/40245588;DTXSID00355921;IMRGVWZLCZERSQ-UHFFFAOYSA-N;BCP21827;CS-D1685;4-chloro-pyridine-3-carboxylic acid;BBL100488;STL554282;AKOS000320190;AB03598;AC-6145;AS-5394;SY006770;4-Chloropyridine-3-carboxylic acid, 96%;AM20050619;FT-0600804;EN300-78482;A19534;W-204425;4-Chloronicotinic acid 4-Chloropyridine-3-carboxylic acid

Chemical Property of 4-Chloronicotinic acid

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.000454mmHg at 25°C
• Melting Point: 139-143 °C
• Refractive Index: 1.59
• Boiling Point: 301.9 °C at 760 mmHg
• PKA: 0.78±0.25(Predicted)
• Flash Point: 136.4 °C
• PSA: 50.19000
• Density: 1.47 g/cm³
• LogP: 1.43320
• Storage Temp.: Keep Cold
• Solubility.: Soluble in organic solvents at 20 deg C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 156.9930561
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

4-ChloronicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC(=C1Cl)C(=O)O
• General Description: **4-Chloronicotinic acid** is a stable and readily prepared compound that serves as a key starting material in synthetic chemistry, particularly for nucleophilic substitution reactions. Its utility is demonstrated in the efficient synthesis of bioactive derivatives like lophocladines A and B, where it acts as a precursor for constructing 2,7-naphthyridine scaffolds with cytotoxic properties. Additionally, its derivatives, such as 3-carboxy-4-chloropyridine, are employed in the design of chiral catalysts for enantioselective acylation reactions, highlighting its versatility in pharmaceutical and catalytic applications.

Technology Process of 4-Chloronicotinic acid

There total 15 articles about 4-Chloronicotinic 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%

4-Chloropyridine (626-61-9) + carbon dioxide (124-38-9,18923-20-1) → 4-chloronicotinic acid (10177-29-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 20 min, 2.) 18 h;

DOI:10.1021/jo00107a004

Reference yield: 75.0%

lithium; 4-chloro-nicotinate → 4-chloronicotinic acid (10177-29-4)

Guidance literature:

With Amberlyst(R) IR-200; In methanol; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(02)00673-7

Reference yield: 73.0%

→ 4-chloronicotinic acid (10177-29-4)

Guidance literature:

upstream raw materials:

4-hydroxynicotinic acid

4-Chloropyridine

carbon dioxide

4-chloro-3-methylpyridine

Downstream raw materials:

methyl 4-chloronicotinate

tert-butyl 4-chloronicotinate

ethyl 3-hydroxyfuro<3,2-c>pyridine-2-carboxylate

5,10-Dihydro-11H-pyrido<4,3-b>-1,5-benzodiazepin-11-one

Refernces

A novel approach for the synthesis of lophocladines A, B and C1 analogues

10.1016/j.tetlet.2011.09.032

The research aims to develop an efficient synthetic route for lophocladines A and B, which are 2,7-naphthyridine derivatives with significant biological activities. These compounds have shown potential in various applications, including as NMDA receptor ligands and cytotoxic agents against cancer cells. The study employs nucleophilic substitution of 4-chloronicotinic acid with a carbanion generated from phenylacetonitrile as a key step, followed by reduction, lactamization, and oxidation to synthesize lophocladine A. Further amination leads to lophocladine B and its C1 analogues. 4-chloronicotinic acid (4) plays a crucial role as a starting material for the synthesis of lophocladines A and B. This compound is chosen due to its stability and ease of preparation, which makes it an ideal precursor for the nucleophilic substitution reaction that is central to the synthetic strategy. The synthesized compounds were evaluated for their cytotoxicity against leukemia cells, revealing that the naphthyridine C1 position significantly affects their potency. The study concludes that the developed synthetic method is efficient and can be applied to produce other C4 analogues, potentially expanding the scope of bioactive compounds for pharmaceutical applications.

Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues

10.1039/b419335k

The research details the development of a new class of chiral 4-(pyrrolidino)-pyridine catalysts derived from (S)-proline for the kinetic resolution of sec-alcohols. These catalysts, including compounds 4 and 5, leverage both van der Waals (π) and H-bonding interactions to achieve enantioselective acylation. The study involved synthesizing these catalysts from simple starting materials like 3-carboxy-4-chloropyridine and various amines. The catalysts were evaluated in the kinetic resolution of mono-protected diols in the presence of isobutyric anhydride, with the (S)-prolinol-derived catalysts showing significant enantioselectivity. The hydroxyl group in these catalysts was found to play a crucial role in determining the selectivity of the acylation reactions. The researchers also explored the influence of different substituents and the impact of H-bonding on the selectivity, using NMR spectroscopy to investigate possible aryl-pyridinium ion π-stacking interactions. The findings suggest that these catalysts represent a novel approach to achieving remote stereochemical control in acylation reactions, with potential applications in enantioselective acyl-transfer processes.