5-(Chloromethyl)-2-phenylpyridine

Base Information

• Chemical Name: 5-(Chloromethyl)-2-phenylpyridine
• CAS No.: 5229-40-3
• Molecular Formula: C12H10ClN
• Molecular Weight: 203.671
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50377178
• Wikidata: Q82166282
• Mol file: 5229-40-3.mol

Synonyms:5-(chloromethyl)-2-phenylpyridine;5229-40-3;5-Chloromethyl-2-phenylpyridine;SCHEMBL2411349;DTXSID50377178;GKDIPQQWMXERFU-UHFFFAOYSA-N;AMY41839;5-(chloromethyl)-2-phenyl-pyridine;MFCD06200953;AKOS005070344;AB23076;FT-0635583;F13761;3Y-0706;A829013;J-516318

Chemical Property of 5-(Chloromethyl)-2-phenylpyridine

Chemical Property:

• Vapor Pressure: 0.000187mmHg at 25°C
• Melting Point: 48-50°C
• Refractive Index: 1.583
• Boiling Point: 338.9 °C at 760 mmHg
• PKA: 3.66±0.10(Predicted)
• Flash Point: 189.2 °C
• PSA: 12.89000
• Density: 1.159g/cm³
• LogP: 3.48740
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 203.0501770
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

5-(Chloromethyl)-2-phenylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC=C(C=C2)CCl
• Uses: 5-(Chloromethyl)-2-phenylpyridine is an intermediate in preparaiton of pyrrolyl- and pyrazolylalkanoic acid derivatives in biological study.

Technology Process of 5-(Chloromethyl)-2-phenylpyridine

There total 5 articles about 5-(Chloromethyl)-2-phenylpyridine 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: 89.0%

2-phenyl-5-hydroxymethylpyridine (4634-09-7) → 2-phenyl-5-pyridylmethyl chloride (5229-40-3)

Guidance literature:

With thionyl chloride; In toluene; at 20 - 100 ℃; for 1h;

Reference yield:

2-phenyl-5-pyridinecarboxaldehyde (63056-20-2) → 2-phenyl-5-pyridylmethyl chloride (5229-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

2: thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; thionyl chloride; In ethanol; dichloromethane;

DOI:10.1021/acs.jmedchem.0c01372

Reference yield:

phenylboronic acid (98-80-6) → 2-phenyl-5-pyridylmethyl chloride (5229-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 0.08 h / 20 °C

1.2: 18 h / 80 °C

2.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; water; 1.2: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.0c01372

upstream raw materials:

2-phenyl-5-hydroxymethylpyridine

2-phenyl-5-pyridinecarboxaldehyde

phenylboronic acid

6-bromonicotinaldehyde

Refernces

• 1、 -. "5-MEMBERED N-HETEROCYCLIC COMPOUNDS WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY". Page 57. . Retrieved 2010/02/07.