2-Chloro-4-methylpyridine

Base Information

• Chemical Name: 2-Chloro-4-methylpyridine
• CAS No.: 3678-62-4
• Molecular Formula: C6H6ClN
• Molecular Weight: 127.573
• Hs Code.: 29349990
• European Community (EC) Number: 222-951-2
• DSSTox Substance ID: DTXSID30190241
• Nikkaji Number: J100.609F
• Wikidata: Q72457748
• Mol file: 3678-62-4.mol

Synonyms:2-Chloro-4-methylpyridine;3678-62-4;2-Chloro-4-picoline;Pyridine, 2-chloro-4-methyl-;MFCD00023418;2-Chloro-4-Methyl Pyridine;4-Picoline, 2-chloro-;2-chloro-4-methyl-pyridine;EINECS 222-951-2;2-Chloro-4methylpyridine;2-chlor-4-methylpyridine;4-methyl-2-chloropyridine;2-chlor-4-methyl pyridine;2-Chloro-4-Methy Pyridine;SCHEMBL111146;DTXSID30190241;2-Chloro-4-methylpyridine, 98%;BBL100687;STL554481;AKOS005145619;AC-3282;CS-W011139;PB10051;PS-3670;SY004677;AM20070056;C1992;FT-0634957;EN300-56134;A823368;J-650305;Q-101494;F0001-1056

Chemical Property of 2-Chloro-4-methylpyridine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.593mmHg at 25°C
• Melting Point: 115°C
• Refractive Index: n20/D 1.529(lit.)
• Boiling Point: 195.3 °C at 760 mmHg
• PKA: 0.94±0.10(Predicted)
• Flash Point: 89.6 °C
• PSA: 12.89000
• Density: 1.15 g/cm³
• LogP: 2.04340
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 127.0188769
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-4-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=NC=C1)Cl
• Uses: 2-Chloro-4-methylpyridine is used as a reagent in the synthesis of the mGLUR5 modulators imidazolyl-ethynyl-pyridines as potential antipsychotics. It is also used in the preparation of trifluoromethyl(pyrimidinyl)azetidinecarboxamides as potent, orally bioavailable TGR5 agonists.

Technology Process of 2-Chloro-4-methylpyridine

There total 19 articles about 2-Chloro-4-methylpyridine 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: 98.7%

2-hydroksy-4-methyl-pyridine (13466-41-6,91914-05-5) → 2-chloro-4-picoline (3678-62-4)

Guidance literature:

With sodium carbonate; In chloroform; water; trichlorophosphate;

Reference yield: 80.0%

picoline (108-89-4) → 2-chloro-4-picoline (3678-62-4)

Guidance literature:

picoline; With n-butyllithium; 2-(N,N-dimethylamino)ethanol; In hexane; at 0 ℃; for 1h;

With hexachloroethane; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;

DOI:10.1002/ejoc.200300243

Reference yield: 76.0%

2,4-dichloropyridine (26452-80-2) + methylmagnesium bromide (75-16-1) → 2-chloro-4-picoline (3678-62-4) + 4-chIoro-2-methylpyridine (3678-63-5)

Guidance literature:

With iron(III)-acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; toluene; at 20 ℃; for 4h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol401508u

upstream raw materials:

6-chloro-4-methylpyridine-2-carboxylic acid

picoline

acetyl hypofluorite

2-Amino-4-methylpyridine

Downstream raw materials:

2-Cyano-4-methylpyridin

2-chloro-4-methylpyridin-N-oxide

4-methyl-2-phenoxypyridine

2-methoxy-4-methyl-pyridine

Refernces

• 1、 -. "Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound". Paragraph 0064-0066. . Retrieved 2018/10/11.
• 2、 Shimada, Yukako,Haraguchi, Ryosuke,Matsubara, Seijiro. "Preparation of an Arenylmethylzinc Reagent with Functional Groups by Chemoselective Cross-Coupling Reaction of Bis(iodoazincio)methane with Iodoarenes". . p. 2395 - 2398. Retrieved 2015/10/19.