2-Bromo-5-(chloromethyl)pyridine

Base Information

• Chemical Name: 2-Bromo-5-(chloromethyl)pyridine
• CAS No.: 168173-56-6
• Molecular Formula: C6H5 Br Cl N
• Molecular Weight: 206.469
• DSSTox Substance ID: DTXSID80423713
• Wikidata: Q82235973
• Mol file: 168173-56-6.mol

Synonyms:2-bromo-5-(chloromethyl)pyridine;168173-56-6;Pyridine, 2-bromo-5-(chloromethyl)- (9CI);2-bromo-5-pyridylmethyl chloride;2-Bromo-5-chloromethylpyridine;SCHEMBL502659;3-chloromethyl-6-bromopyridine;DTXSID80423713;MFCD10697565;AKOS022177994;AB59933;DS-14144;FT-0743603;PYRIDINE, 2-BROMO-5-(CHLOROMETHYL)-;C73235;EN300-1914883

Chemical Property of 2-Bromo-5-(chloromethyl)pyridine

Chemical Property:

• Vapor Pressure: 0.00494mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 285ºC at 760 mmHg
• PKA: 0.02±0.10(Predicted)
• Flash Point: 126.2ºC
• PSA: 12.89000
• Density: 1.631g/cm3
• LogP: 2.58290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 204.92939
• Heavy Atom Count: 9
• Complexity: 89.1

Purity/Quality:

99% ^*data from raw suppliers

2-BROMO-5-(CHLOROMETHYL)PYRIDINE 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1CCl)Br

Technology Process of 2-Bromo-5-(chloromethyl)pyridine

There total 4 articles about 2-Bromo-5-(chloromethyl)pyridine 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: 91.0%

2-bromo-5-(hydroxymethyl)pyridine (122306-01-8) → 2-bromo-5-pyridylmethyl chloride (168173-56-6)

Guidance literature:

2-bromo-5-(hydroxymethyl)pyridine; With thionyl chloride; at -60 ℃; for 1h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

6-bromonicotinaldehyde (149806-06-4) → 2-bromo-5-pyridylmethyl chloride (168173-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; ethanol / 20 °C / Inert atmosphere

2: thionyl chloride / 1 h / -60 - 20 °C

With sodium tetrahydroborate; thionyl chloride; ethanol;

DOI:10.1021/acs.inorgchem.6b00972

Reference yield:

6-bromonicotinic acid (6311-35-9) → 2-bromo-5-pyridylmethyl chloride (168173-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C

2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 20 °C / Cooling with ice

With thionyl chloride; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm201657x

upstream raw materials:

2-bromo-5-(hydroxymethyl)pyridine

6-bromonicotinic acid

6-bromonicotinaldehyde

Downstream raw materials:

(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

C₁₅H₁₈N₄

(6-bromopyridine-3-yl)acetonitrile

Refernces

• 1、 -. "CDK4/6 INHIBITORS AND USE THEREOF". Paragraph 731; 734; 735. . Retrieved 2019/03/05.
• 2、 -. "Benzimidazole derivatives, preparation methods and uses theirof". Page/Page column 31. . Retrieved 2018/12/01.