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

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

Uses

Used in Pesticide Industry:
2-Chloro-3-picoline is used as an active ingredient in the production of imidacloprid, a systemic insecticide. It serves as an insect neurotoxin for controlling a wide range of pests, including aphids, whiteflies, and thrips, which are detrimental to agricultural crops and gardens. The application of 2-Chloro-3-picoline in this context is due to its effectiveness in targeting the central nervous system of insects, leading to paralysis and death.
Used in Chemical Synthesis:
In addition to its role in the pesticide industry, 2-Chloro-3-picoline can also be utilized as a building block in the synthesis of various other chemicals and pharmaceuticals. Its unique chemical structure allows it to be a versatile intermediate for creating a range of compounds with different applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

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

Downstream Products

• 20970-75-6 2-cyano-3-methylpyridine 
• 91668-83-6 2-Chloro-3-methylpyridine N-oxide 
• 2942-59-8 2-chloronicotinic acid 
• 104396-10-3 1-(3-Methyl-2-pyridinyl)piperazine 
• 51933-79-0 3-methyl-2-phenoxypyridine 
• 79179-80-9 1-Benzyl-4-[4-(3-methyl-pyridin-2-ylamino)-benzyl]-piperazine-2,3-dione 
• 81528-65-6 2-(2-aminoethylamino)-3-methylpyridine 
• 10273-90-2 2-phenyl-3-methylpyridine 
• 582325-38-0 (R)-3-Methyl-1-(3-methyl-pyridin-2-yl)-piperazine 
• 889359-32-4 6-(3-methyl-pyridin-2-yl)-2-(4-trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-indazol-3-one 

Relevant articles and documents

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.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

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.

Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound

The invention provides a preparation method of a non-transition metal-catalyzed 2-halogenated pyridine compound. The 2-halogenated pyridine compound is an important component of many medicines and bioactive molecules and has important application in the fields of organic synthesis, medicinal chemistry and the like and wide market prospects. The invention relates to the preparation method of the non-transition metal-catalyzed 2-halogenated pyridine compound. According to the method, pyridine-2-carboxylic acid, derivatives of the pyridine-2-carboxylic acid, NaF, KF, CsF, TBAF, NaCl, KCl, CsCl, TBAC, NCS, NaBr, KBr, CsBr, Br2, TBAB, NBS, NaI, KI, CsI, I2 and NIS are used as raw materials, and under the presence of base and an accelerant and mild conditions, the 2-halogenated pyridine compoundis synthesized. The method has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction conditions are mild and the like; the method has great use value and socialand economic benefits.

PROCESS FOR MAKING 2-CHLORO-5-METHYLPYRIDINE

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

PROCESS FOR MAKING 2-CHLORO-5-METHYLPYRIDINE

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

Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides

Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.

Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene

Diphosgene and triphosgene in the presence of amines were found to be an excellent chlorinating agents with high selectivity for the preparation of chloromethylpyridines and chloropyridines from picoline-N-oxides and pyridine-N-oxides respectively.

Process for the preparation of 2-halogeno-pyridine derivatives

A process for the preparation of a 2-halogeno-pyridine of the formula STR1 in which X represents halogen and Y represents halogen, nitro, formyl, cyano, carboxyl, carbamoyl, alkyl, halogenoalkyl, alkoxyalkyl, dialkoxyalkyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, which comprises in a first stage reacting a pyridine 1-oxide of the formula STR2 with an organic nitrogen base A and an electrophilic compound, optionally in the presence of a diluent, to produce a compound of the formula STR3 in which A represents the radical of an organic nitrogen base, and Z- represents an anion formed from an electrophilic compound, optionally isolating and optionally purifying the compound of the formula (III).

Utilizing Acetyl Hypofluorite for Chlorination, Bromination, and Etherification of the Pyridine System

Acetyl hypofluorite, which is easily made from F2, possesses a strong electrophilic fluorine.This electrophile is able to attach itself to the nitrogen atom of pyridine and activate the ring toward nucleophilic attacks.The ultimate elimination of HF results in an overall easy nucleophilic displacement of the hydrogen of the important 2-position .The nucleophiles used: Clδ-, Brδ-, ROδ-, originate from solvents such as CH2Cl2, CH2Br2, and various primary alcohols.Thus, 2-halo- or 2-alkoxypyridines were formed.The reaction conditions (room temperature, very short reaction times, and good yields) transform the task of direct substitution of the pyridine ring from an extremely difficult to a very easy procedure.