2-Chloro-6-phenylnicotinic acid

Base Information

• Chemical Name: 2-Chloro-6-phenylnicotinic acid
• CAS No.: 69750-01-2
• Molecular Formula: C12H8ClNO2
• Molecular Weight: 233.654
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID00498822
• Nikkaji Number: J2.666.187K
• Wikidata: Q82349125
• Mol file: 69750-01-2.mol

Synonyms:2-Chloro-6-phenylnicotinic acid;69750-01-2;2-Chloro-6-phenylpyridine-3-carboxylic acid;MFCD09027892;Ethyl5-aminovalerate;SCHEMBL10900818;DTXSID00498822;AKOS005255730;VS-12790;2-Chloro-6-phenylnicotinic acid, AldrichCPR

Chemical Property of 2-Chloro-6-phenylnicotinic acid

Chemical Property:

• Vapor Pressure: 2.11E-07mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 408.4°C at 760 mmHg
• Flash Point: 200.8°C
• PSA: 50.19000
• Density: 1.355g/cm³
• LogP: 3.10020
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 233.0243562
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-Chloro-6-phenylnicotinic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC(=C(C=C2)C(=O)O)Cl

Technology Process of 2-Chloro-6-phenylnicotinic acid

There total 5 articles about 2-Chloro-6-phenylnicotinic 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: 81.0%

2,6-dichloropyridine-3-carboxylic acid (38496-18-3) + phenylboronic acid (98-80-6) → 2-chloro-6-phenylpyridine-3-carboxylic acid (69750-01-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1002/jhet.5570450646

Reference yield:

2-chloro-3-cyano-6-phenylpyridine (43083-14-3) → 2-chloro-6-phenylpyridine-3-carboxylic acid (69750-01-2)

Guidance literature:

With sulfuric acid; sodium nitrite; Yield given. Multistep reaction; 1.) 120 deg C, 2 h; 2.) water, 80 deg C, 0.5 h;

DOI:10.1248/cpb.30.4314

Reference yield:

3-cyano-2-hydroxy-6-phenylpyridine (43083-13-2) → 2-chloro-6-phenylpyridine-3-carboxylic acid (69750-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93.8 percent / PCl₅, POCl₃ / 1 h / 150 °C

2: 1.) 90percent H₂SO₄; 2.) sodium nitrite / 1.) 120 deg C, 2 h; 2.) water, 80 deg C, 0.5 h

With phosphorus pentachloride; sulfuric acid; sodium nitrite; trichlorophosphate;

DOI:10.1248/cpb.30.4314

upstream raw materials:

2-chloro-3-cyano-6-phenylpyridine

3-cyano-2-hydroxy-6-phenylpyridine

2,6-dichloropyridine-3-carboxylic acid

phenylboronic acid

Downstream raw materials:

6-phenylpyridine-3-carboxylic acid

2-Chloro-6-phenyl-N-(1H-tetrazol-5-yl)-nicotinamide

2-chloro-6-phenylpyridine-3-carboxylic acid methyl ester

2-methoxy-6-phenylpyridine-3-carboxylic acid

Refernces

• 1、 -. "PYRIDINE DERIVATIVES AND APPLICATION OF ANTI-MACOBACTERIUM THEREOF". Paragraph 0290; 0292; 0293. . Retrieved 2016/10/08.
• 2、 Ma, Mingliang,Li, Chengwei,Li, Xiaoyan,Wen, Ke,Liu, Yahu A.. "Efficient synthesis of 6-aryl-2-chloronicotinic acids via Pd catalyzed regioselective suzuki coupling of 2,6-dichloronicotinic acid". experimental part. p. 1847 - 1849. Retrieved 2009/06/08.