65169-38-2

Basic information

• Product Name: 2-Chloro-4-methylpyridine-3-carbonitrile
• Synonyms: 2-Chloro-4-methylpyridine-3-carbonitrile;2-chloro-4-methylnicotinonitrile;2-Chloro-4-methyl-3-cyano-pyridine
• CAS NO: 65169-38-2
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;Pyridine
• Mol File: 65169-38-2.mol

Chemical Properties

• Boiling Point: 286.365oC at 760 mmHg
• Flash Point: 126.989oC
• Appearance: /
• Density: 1.269g/cm3
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-Chloro-4-methylpyridine-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-methylpyridine-3-carbonitrile(65169-38-2)
• EPA Substance Registry System: 2-Chloro-4-methylpyridine-3-carbonitrile(65169-38-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 65169-38-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-4-methylpyridine-3-carbonitrile is used as an intermediate in the synthesis of various chemical compounds. Its unique structure allows it to be a valuable building block for creating a wide range of products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-4-methylpyridine-3-carbonitrile is used as a key component in the development of new drugs. Its presence in the molecular structure can contribute to the desired pharmacological properties, such as potency, selectivity, and bioavailability, making it an essential part of the drug discovery process.
Used in Agrochemical Industry:
2-Chloro-4-methylpyridine-3-carbonitrile is also utilized in the agrochemical industry, where it serves as a precursor for the synthesis of various agrochemical products. Its role in the production of pesticides, herbicides, and other crop protection agents highlights its importance in ensuring agricultural productivity and food security.
Used in Research and Development:
In the field of research and development, 2-Chloro-4-methylpyridine-3-carbonitrile is employed as a reagent in various chemical reactions and experiments. Its versatility and reactivity make it a valuable tool for scientists and researchers working on new chemical processes and methodologies.

InChI:InChI=1/C7H5ClN2/c1-5-2-3-10-7(8)6(5)4-9/h2-3H,1H3

Upstream product

• 93271-59-1 2-hydroxy-4-methylpyridine-3-carbonitrile 
• 93271-59-1 1,2-dihydro-2-oxo-4-methylpyridine-3-carbonitrile 
• 13166-10-4 isopropylidenemalonodinitrile 
• 71493-72-6 2-(4-(dimethylamino)but-3-en-2-ylidene)malononitrile 
• 67-56-1 methanol 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 109-77-3 malononitrile 
• 875-35-4 2,6-dichloro-4-methylnicotinonitrile 
• 5444-02-0 2,6-dihydroxy-3-cyano-4-methylpyrimidine 

Downstream Products

• 149379-71-5 2-methoxy-4-methylpyridine-3-carbonitrile 
• 243469-62-7 3-hydroxymethyl-2-methoxy-4-methylpyridine 
• 243469-67-2 4-(2-hydroxy-2-phenylethyl)-2-methoxypyridine-3-carbonitrile 
• 243469-68-3 methanesulfonic acid 2-(3-cyano-2-methoxy-pyridin-4-yl)-1-phenyl-ethyl ester 
• 243469-77-4 methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate 
• 152362-01-1 2-chloro-4-methyl-3-pyridinecarboxamide 
• 133627-45-9 3-Amino-2-chloro-4-methylpyridine 
• 498580-78-2 4-methyl-1H-pyrazolo[3,4-b]pyridin-3-amine 
• 129618-40-2 Nevirapine 
• 133627-47-1 N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide 
• 1698293-93-4 4-methyl-2-(1-methylethyl)-3-pyridinamine 

Relevant articles and documents

Preparation method of Sotorasib intermediate

The invention discloses a preparation method of a Sotorasib intermediate 2-isopropyl-3-amino-4-methylpyridine. The preparation method comprises the following specific steps of: (1) carrying out a reaction on 3-cyano-4-methyl-2-pyridone and a halogenating reagent to obtain 2-halogenated-3-cyano-4-methylpyridine; (2) making the 2-halogenated-3-cyano-4-methylpyridine with an isopropyl Grignard reagent under the action of a catalyst, so as to obtain 2-isopropyl-3-cyano-4-methylpyridine; (3) carrying out hydrolysis on the 2-isopropyl-3-cyano-4-methylpyridine, so as to obtain 2-isopropyl-4-methyl nicotinamide; and (4) carrying out Hofmann rearrangement on the 2-isopropyl-4-methyl nicotinamide, sodium hydroxide and a sodium hypochlorite solution, so as to obtain the 2-isopropyl-3-amino-4-methylpyridine. The preparation method disclosed by the invention is low in cost and simple to operate, and is a novel method for synthesizing the 2-isopropyl-3-amino-4-methylpyridine.

Increasing global access to the high-volume HIV drug nevirapine through process intensification

Access to affordable medications continues to be one of the most pressing issues for the treatment of disease in developing countries. For many drugs, synthesis of the active pharmaceutical ingredient (API) represents the most financially important and technically demanding element of pharmaceutical operations. Furthermore, the environmental impact of API processing has been well documented and is an area of continuing interest in green chemical operations. To improve drug access and affordability, we have developed a series of core principles that can be applied to a specific API, yielding dramatic improvements in chemical efficiency. We applied these principles to nevirapine, the first non-nucleoside reverse transcriptase inhibitor used in the treatment of HIV. The resulting ultra-efficient (91% isolated yield) and highly-consolidated (4 unit operations) route has been successfully developed and implemented through partnerships with philanthropic entities, increasing access to this essential medication. We anticipate an even broader global health impact when applying this model to other active ingredients.

Method for preparing 2-chloro-4-methylpyridine-3-carbonitrile

The invention discloses a method for preparing 2-chloro-4-methylpyridine-3-carbonitrile. The method comprises the following steps: at -20 DEG C to 50 DEG C, a hydrogen chloride solution is used for treating raw materials containing 4,4-dicyano-3-methyl-3-butenal dimethyl acetal. 2-chloro-4-methylpyridine-3-carbonitrile whose HPLC purity reaches 99% or above can be conveniently obtained, which has important meanings for subsequent preparation of high purity 2-chloro-4-methylpyridine-3-carbonitrile and nevirapine; the method has the advantages of short process route, simple operation, high yield, low cost, etc., a highly toxic product phosphorous oxychloride is avoided, discharge of waste water is reduced, and the method is very suitable for industrial production.

HETEROCYCLIC COMPOUNDS AS EP4 RECEPTOR ANTAGONISTS

The present invention provides a compound represented by the formula (1): wherein each symbol is as defined in the specification or a salt thereof has an EP4 receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of EP4 receptor associated diseases (e.g., rheumatoid arthritis, aortic aneurysm, endometriosis, ankylosing spondylitis, inflammatory breast cancer etc.) and the like.

LOWCOST, HIGH YIELD SYNTHESIS OF NEVIRAPINE

Improved methods of producing the HIV drug substance, nevirapine are provided. The methods employ a cost effective and high yield synthetic methods for preparing the nevirapine building block 2-chloro-3-amino-4-picoline (CAPIC) and 2-cyclopropyl amino nicotinate (Me-CAN), and improvements in other steps of nevirapine synthesis.

METHODS OF MAKING 2-HALONICOTINONITRILES

A method of making a 2-halonicotinonitrile comprises reacting an alkylidene nitrile with a C1-compound in an organic solvent and a dehydrating agent. The dehydrating agent substantially retards dimerization of the alkylidene nitrile during the reaction. The enamine intermediate that forms from the reaction is cyclized using a halide donor to make the 2-halonicotinonitrile.

Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles

Pyridines with 2,3,4 and/or 5 substitution remain challenging to prepare. Existing strategies to form multisubstituted 2-halonicotinonitriles via enamines suffer from dimerization of the starting alkylidene malononitriles resulting in low yields. Through alteration of reaction conditions, a new high yielding method into enamines was realized by condensing DMF-DMA and alkylidene malononitriles in the presence of substoichiometric acetic anhydride. Cyclization of the resulting enamines under Pinner conditions provided 2-halonicotinonitriles in high overall yields.

Azaindenoisoquinolines as topoisomerase i inhibitors and potential anticancer agents: A systematic study of structure-activity relationships

A comprehensive study of a series of azaindenoisoquinoline topoisomerase I (Top1) inhibitors is reported. The synthetic pathways have been developed to prepare 7-, 8-, 9-, and 10-azaindenoisoquinolines. The present study shows that 7-azaindenoisoquinolines possess the greatest Top1 inhibitory activity and cytotoxicity. Additionally, the introduction of a methoxy group into the D-ring of 7-azaindenoisoquinolines improved their biological activities, leading to new lead molecules for further development. A series of QM calculations were performed on the model "sandwich" complexes of azaindenoisoquinolines with flanking DNA base pairs from the Drug-Top1-DNA ternary complex. The results of these calculations demonstrate how changes in two forces contributing to the π-π stacking (dispersion and charge-transfer interactions) affect the binding of the drug to the Top1-DNA cleavage complex and thus modulate the drug's Top1 inhibitory activity.

A concise synthesis of 2-chloro-3-amino-4-methylpyridine

An improved and commercially valuable process is developed for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. The total yield of the process is 62.1%. The pure CAPIC sample was confirmed with FTIR, 1H NMR, and 13C NMR spectra.

BACTERICIDE COMPOSITION AND METHOD OF CONTROLLING PLANT DISEASE

It is to provide a fungicidal composition having stable and high fungicidal effects against cultivated crops infected with plant diseases resulting from plant diseases. A fungicidal composition containing as active ingredients (a) a benzoylpyridine derivative represented by the formula (I) or its salt: (wherein X is a halogen atom, a nitro group, a substitutable hydrocarbon group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group, a hydroxyl group, a substitutable alkylthio group, a cyano group, a carboxyl group which may be esterified or amidated, or a substitutable amino group, n is 1, 2, 3 or 4; R1 is a substitutable alkyl group, R2' is a substitutable alkyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group or a hydroxyl group, p is 1, 2 or 3, and R2" is a substitutable alkoxy group or a hydroxyl group, provided that at least two of R2' and R2" may form a condensed ring containing an oxygen atom) and (b) at least one another fungicide.