18368-76-8

Basic information

• Product Name: 2-Chloro-3-picoline
• Synonyms: 2-CHLORO-3-METHYLPYRIDINE;2-CHLORO-3-PICOLINE;2-CHLORO-3-METHYLPYRIDINE 98%;2-CHLORO-3-METHYLPYRRIDINE;2-CHLORO-3-PICOLINE 2-CHLORO-3-METHYLPYRIDINE;2-CHLORO-3-METHYLPYRIDINE (2-CHLORO-3-PICOLINE);2-Chloro-3-methylpyridine, 98+%;2-Choro-3-methypyridine
• CAS NO: 18368-76-8
• Molecular Formula: C₆H₆ClN
• Molecular Weight: 127.57
• EINECS: 242-242-1
• Product Categories: Pyridine;Pyridines;Chloropyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Chlorinated heterocyclic series;pyridine series;alkyl chloride
• Mol File: 18368-76-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 192-193 °C751 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Colorless to light yellow/Liquid
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.679mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 0.75±0.10(Predicted)
• BRN: 107895
• CAS DataBase Reference: 2-Chloro-3-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-picoline(18368-76-8)
• EPA Substance Registry System: 2-Chloro-3-picoline(18368-76-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 18368-76-8(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid

Uses

2-Chloro-3-methylpyridine is an active ingredient and a major constituent of imidaclopide, a systemic insecticide that acts as insect neurotoxin and belongs to a class of chemical called the neonicotinoids.

InChI:InChI=1/C6H6ClN/c1-5-3-2-4-8-6(5)7/h2-4H,1H3

Upstream product

• 1003-73-2 3-picoline-N-oxide 
• 1003-56-1 3-methylpyridin-2-ol 
• 4021-07-2 3-methyl-pyridine-2-carboxylic acid 
• 75-44-5 phosgene 
• 108-99-6 3-Methylpyridine 
• 1984-23-2 p-nitrophenyl isocyanide 
• 67-66-3 chloroform 
• 26751-09-7 3-methyl-pyridine-1-oxide ; hydrochloride 
• 125014-89-3 Nitrile of 2-Methyl-2-chloro-5-oxopentanoic acid 
• 1003-56-1 3-Methyl-1H-pyridin-2-one 
• 78948-09-1 acetyl hypofluorite 
• 109-09-1 2-chloropyridine 
• 74-88-4 methyl iodide 
• 824-72-6 P,P-dichlorophenylphosphine oxide 

Downstream Products

• 20970-75-6 2-cyano-3-methylpyridine 
• 91668-83-6 2-Chloro-3-methylpyridine N-oxide 
• 2942-59-8 2-chloronicotinic acid 
• 10273-90-2 2-phenyl-3-methylpyridine 
• 582325-38-0 (R)-3-Methyl-1-(3-methyl-pyridin-2-yl)-piperazine 
• 1258786-30-9 3-methyl-2-(toluene-4-sulfonyl)-pyridine 
• 2732-12-9 2-(benzyloxy)-3-methylpyridine 
• 58802-11-2 1-benzyl-3-methylpyridin-2(1H)-one 
• 1388624-22-3 N-((4-butylphenyl)(phenyl)methyl)-3-methylpyridin-2-amine 
• 1388624-23-4 N-((4-(dimethylamino)phenyl)(phenyl)methyl)-3-methylpyridin-2-amine 
• 1388624-24-5 ethyl 4-(((3-methylpyridin-2-yl)amino)(phenyl)methyl)benzoate 
• 1416556-12-1 N-[(4-isopropoxyphenyl)(phenyl)methyl]-3-methylpyridin-2-amine 
• 1388624-25-6 methyl 4-(((3-methylpyridin-2-yl)amino)(phenyl)methyl)benzoate 
• 1370412-44-4 3-methyl-N-{phenyl[4-(trifluoromethyl)phenyl]methyl}-pyridin-2-amine 

Relevant articles and documents

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Extending motifs in lithiocuprate chemistry: Unexpected structural diversity in thiocyanate complexes

The new area of lithio(thiocyanato)cuprates has been developed. Using inexpensive, stable and safe CuSCN for their preparation, these complexes revealed Lipshutz-type dimeric motifs with solvent-dependent point group identities; planar, boat-shaped and chair shaped conformers are seen in the solid state. In solution, both Lipshutz-type and Gilman structures are clearly seen. Since the advent in 2007 of directed ortho cupration, effort has gone into understanding the structure-reactivity effects of amide ligand variation in and alkali metal salt abstraction from Lipshutz-type cuprates such as (TMP)2Cu(CN)Li2(THF) 1 (TMP = 2,2,6,6-tetramethylpiperidide). The replacement of CN- with SCN- is investigated presently as a means of improving the safety of lithium cuprates. The synthesis and solid state structural characterization of reference cuprate (TMP)2Cu(CN)Li2(THP) 8 (THP = tetrahydropyran) precedes that of the thiocyanate series (TMP)2Cu(SCN)Li2(L) (L = OEt29, THF 10, THP 11). For each of 9-11, preformed TMPLi was combined with CuSCN (2 : 1) in the presence of sub-stoichiometric Lewis base (0.5 eq. wrt Li). The avoidance of Lewis basic solvents incurs formation of the unsolvated Gilman cuprate (TMP)2CuLi 12, whilst multidimensional NMR spectroscopy has evidenced the abstraction of LiSCN from 9-11 in hydrocarbon solution and the in situ formation of Gilman reagents. The synthetic utility of 10 is established in the selective deprotometalation of chloropyridine substrates, including effecting transition metal-free homocoupling in 51-69% yield.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

PROCESS FOR MAKING 2-CHLORO-5-METHYLPYRIDINE

Processes for the preparation of 2-chloro-5-methylpyridine are described.