2-Chloro-3-(chloromethyl)pyridine

Base Information

• Chemical Name: 2-Chloro-3-(chloromethyl)pyridine
• CAS No.: 89581-84-0
• Molecular Formula: C6H5Cl2N
• Molecular Weight: 162.018
• Hs Code.: 2933399090
• European Community (EC) Number: 677-282-2
• UNII: 277P6B9NBT
• DSSTox Substance ID: DTXSID80468063
• Nikkaji Number: J2.855.780I
• Wikidata: Q72517746
• Mol file: 89581-84-0.mol

Synonyms:2-chloro-3-(chloromethyl)pyridine;89581-84-0;2-Chloro-3-chloromethylpyridine;Pyridine, 2-chloro-3-(chloromethyl)-;MFCD09835107;SCHEMBL669824;277P6B9NBT;DTXSID80468063;QWIIJVGEBIQHSW-UHFFFAOYSA-N;2-chloro-3-(chloromethyl)-pyridine;(2-chloro-3-pyridyl)methyl chloride;AKOS006230704;CS-W016128;PB14751;2-Bromo-3-(chloromethyl)pyridine, 96%;2-CHLORO-3-CHLOROMETHYL-PYRIDINE;2-CHLORO-3-PYRIDYLMETHYL CHLORIDE;AS-18636;SY042081;A7387;FT-0757778;EN300-63894;A861133;A911257;2-Chloronicotinoyl Chloride

Chemical Property of 2-Chloro-3-(chloromethyl)pyridine

Chemical Property:

• Vapor Pressure: 0.007mmHg at 25°C
• Boiling Point: 278.951oC at 760 mmHg
• PKA: -0.18±0.10(Predicted)
• Flash Point: 122.505oC
• PSA: 12.89000
• Density: 1.632g/cm3
• LogP: 2.47380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 160.9799046
• Heavy Atom Count: 9
• Complexity: 87.1

Purity/Quality:

97% ^*data from raw suppliers

2-Chloro-3-(chloromethyl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Cl)CCl

Technology Process of 2-Chloro-3-(chloromethyl)pyridine

There total 7 articles about 2-Chloro-3-(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: 100.0%

(2-chloropyrid-3-yl)methanol (42330-59-6) → 2-chloro-3-(chloromethyl)pyridine (89581-84-0)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane;

DOI:10.1016/j.tetlet.2010.05.121

Reference yield: 87.4%

2 chloro-3-methylpyridine (18368-76-8) → 2-chloro-3-(chloromethyl)pyridine (89581-84-0)

Guidance literature:

With chlorine; at 110 ℃; for 30h; Temperature;

Reference yield:

nicotinic acid (59-67-6) → 2-chloro-3-(chloromethyl)pyridine (89581-84-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dihydrogen peroxide; acetic acid / toluene / Reflux

1.2: Reflux

2.1: sulfuryl dichloride / methanol / 0 - 20 °C

3.1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran / 0 - 20 °C

4.1: sulfuryl dichloride / dichloromethane / 0 - 20 °C

With sodium tetrahydroborate; sulfuryl dichloride; dihydrogen peroxide; acetic acid; calcium chloride; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/j.cclet.2011.01.042

upstream raw materials:

(2-chloropyrid-3-yl)methanol

2-chloro-3-carbaldehydepyridine

nicotinic acid

2-Chloronicotinoyl chloride

Downstream raw materials:

3-(2-chloropyrid-3-ylmethoxy)-1-benzhydrylazetidine

spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

tert-butyl 2'-oxo-1',2'-dihydro-1H-spiro[piperidine-4,3'-pyrrolo[2.3-b]pyridine]-1-carboxylate

2-chloro-3-carbaldehydepyridine

Refernces

• 1、 -. "A 2 - chloro - 3 - pyridine formaldehyde synthetic method (by machine translation)". Paragraph 0029; 0030; 0038; 0039; 0040. . Retrieved 2018/01/12.
• 2、 Takai, Kentaro,Inoue, Yasunao,Konishi, Yasuko,Suwa, Atsushi,Uruno, Yoshiharu,Matsuda, Harumi,Nakako, Tomokazu,Sakai, Mutsuko,Nishikawa, Hiroyuki,Hashimoto, Gakuji,Enomoto, Takeshi,Kitamura, Atsushi,Uematsu, Yasuaki,Kiyoshi, Akihiko,Sumiyoshi, Takaaki. "Discovery of N-substituted 7-azaindoline derivatives as potent, orally available M1 and M4 muscarinic acetylcholine receptors selective agonists". . p. 3189 - 3193. Retrieved 2014/06/24.