5-Bromo-2-(chloromethyl)pyridine

Base Information

• Chemical Name: 5-Bromo-2-(chloromethyl)pyridine
• CAS No.: 168823-76-5
• Molecular Formula: C6H5BrClN
• Molecular Weight: 206.469
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60464725
• Wikidata: Q82290177
• Mol file: 168823-76-5.mol

Synonyms:5-bromo-2-(chloromethyl)pyridine;168823-76-5;5-Bromo-2-chloromethyl-pyridine;Pyridine, 5-broMo-2-(chloroMethyl)- (9CI);PYRIDINE, 5-BROMO-2-(CHLOROMETHYL)-;MFCD10697592;SCHEMBL508242;DTXSID60464725;YESFMWFCJUGBLH-UHFFFAOYSA-N;AKOS012256924;AB60010;DS-14186;SY060820;Pyridine,5-bromo-2-(chloromethyl)-(9ci);CS-0043013;FT-0699463;J-516837

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

Chemical Property:

• Vapor Pressure: 0.05mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 243.4 °C at 760 mmHg
• PKA: 1.35±0.22(Predicted)
• Flash Point: 101 °C
• PSA: 12.89000
• Density: 1.631 g/cm³
• LogP: 2.58290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• 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:

97% ^*data from raw suppliers

5-Bromo-2-(chloromethyl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1Br)CCl

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

There total 7 articles about 5-Bromo-2-(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: 94.0%

(5-bromopyridin-2-yl)methanol (88139-91-7) → 5-bromo-2-(chloromethyl)pyridine (168823-76-5)

Guidance literature:

With thionyl chloride; In toluene; at 20 ℃;

DOI:10.1142/S108842461000232X

Reference yield:

methyl 5-bromopicolinate (29682-15-3) → 5-bromo-2-(chloromethyl)pyridine (168823-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C

2: thionyl chloride / toluene / 3 h / 20 °C

With sodium tetrahydroborate; thionyl chloride; In methanol; toluene;

DOI:10.1002/chem.201101272

Reference yield:

trifluoro-acetic acid 5-bromo-pyridin-2-ylmethyl ester (900186-88-1) → 5-bromo-2-(chloromethyl)pyridine (168823-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHCO₃ / H₂O / 20 °C / pH 8

2: thionyl chloride / CH₂Cl₂ / 18 h / 20 °C

With thionyl chloride; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1021/jo035157z

upstream raw materials:

(5-bromopyridin-2-yl)methanol

trifluoro-acetic acid 5-bromo-pyridin-2-ylmethyl ester

5-bromo-2-(bromomethyl)pyridine

5-bromo-pyridine-2-carbaldehyde

Downstream raw materials:

[(5-bromo-2-pyridinyl)methyl]-phosphonic acid diethyl ester

5-(5-bromo-picol-2-yl)-10,15,20-trimesitylporphinato-Zn(II)

2-(5-bromopyridin-2-yl)acetonitrile

2,2-difluoro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-{6-[(methanesulfonylmethoxyamino)methyl]pyridin-3-yl}phenyl)ethyl]acetamide