5444-01-9

Basic information

• Product Name: 3-Cyano-4-methylpyridine
• Synonyms: 3-CYANO-4-METHYLPYRIDINE;4-METHYLNICOTINONITRILE;3-Cyano-4-picoline;4-Methylnicotinotrile;4-Methylpyridine-3-carbonitrile;3-Pyridinecarbonitrile, 4-methyl-;3-Cyano-4-methylpyridine ,98%;4-Methyl-3-pyridinecarbonitrile 4-Methylnicotinonitrile
• CAS NO: 5444-01-9
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• EINECS: -0
• Product Categories: Pyridines;Pyridine;Pyridines derivates;Heterocycle-Pyridine series
• Mol File: 5444-01-9.mol

Chemical Properties

• Melting Point: 41-44°C
• Boiling Point: 108-111°C 20mm
• Flash Point: 108-111°C/20mm
• Appearance: White powder
• Density: 1.084 g/cm³
• Vapor Pressure: 0.061mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• PKA: 2.45±0.18(Predicted)
• BRN: 112016
• CAS DataBase Reference: 3-Cyano-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyano-4-methylpyridine(5444-01-9)
• EPA Substance Registry System: 3-Cyano-4-methylpyridine(5444-01-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-36/38-22
• Safety Statements: 22-36/37/39-36-26-36/37
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5444-01-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyano-4-methylpyridine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its application is primarily due to its ability to be incorporated into the molecular structures of different drugs, enhancing their therapeutic properties.
Used in Anticancer Applications:
In the field of oncology, 3-Cyano-4-methylpyridine is utilized for the preparation of a series of azaindenoisoquinoline topoisomerase I inhibitors. These inhibitors play a significant role in the development of potential anticancer agents, as they target and disrupt the activity of topoisomerase I, an enzyme essential for DNA replication in cancer cells. By inhibiting this enzyme, the replication process is disrupted, leading to the prevention of cancer cell proliferation and the potential regression of tumors.
Used in Drug Synthesis:
3-Cyano-4-methylpyridine is also employed in the synthesis of other drug compounds, where its unique structural features allow for the creation of molecules with specific biological activities. Its use in drug synthesis is driven by the need for novel and effective therapeutic agents to address various medical conditions and challenges.

InChI:InChI=1/C7H6N2/c1-6-2-3-9-5-7(6)4-8/h2-3,5H,1H3

Upstream product

• 695-34-1 2-Amino-4-methylpyridine 
• 67-66-3 chloroform 
• 5444-02-0 2,6-dihydroxy-3-cyano-4-methylpyrimidine 
• 544-92-3 copper(I) cyanide 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 143-33-9 sodium cyanide 
• 557-21-1 dicyanozinc 
• 875-35-4 2,6-dichloro-4-methylnicotinonitrile 
• 38824-75-8 2,6-dibromo-4-methylpyridine-3-carbonitrile 
• 7250-50-2 4-Methyl-3-formyl-pyridin-oxim 
• 51227-28-2 4-methylnicotinaldehyde 
• 7250-52-4 4-methyl-3-pyridinecarboxamide 
• 3222-50-2 4-methylnicotinic acid 
• 100-54-9 pyridine-3-carbonitrile 

Downstream Products

• 3222-50-2 4-methylnicotinic acid 
• 7250-52-4 4-methyl-3-pyridinecarboxamide 
• 39585-56-3 4-(trans-2-furan-2-yl-vinyl)-nicotinamide 
• 39585-52-9 4-(trans-2-thiophen-2-yl-vinyl)-nicotinamide 
• 39585-54-1 4-(trans-2-thiophen-3-yl-vinyl)-nicotinamide 
• 36106-46-4 4-[1,3]dithian-2-yl-nicotinonitrile 
• 58790-51-5 1-oxo-1H-pyrano[3,4-c]pyridine-3-carboxylic acid ethyl ester 
• 109374-24-5 (+/-)-5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino<2,1-b><2,7>naphthyridine-8-imine 
• 87496-11-5 Sodium; (Z)-2-(3-cyano-pyridin-4-yl)-ethenolate 
• 158978-53-1 1-Naphthyl-3-(4-methylpyridyl)-keton 
• 51227-30-6 1-(4-methyl-pyridin-3-yl)-ethanone 
• 131423-59-1 4-<2-<(2R,4R)-4-benzyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridinecarboxamide 
• 116965-53-8 8,3,13b,14-tetrahydroindolo<2',3':3,4>pyrido<1,2-b><2,7>naphthyridin-5(7H)-imine 
• 146501-60-2 4-<2-<(2R,4R)-4-t butyl dimethylsilyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide 

Relevant articles and documents

Alkylidene Dihydropyridines Are Surrogates for Pyridylic Anions in the Conjugate Addition to α,β-Unsaturated Ketones

We show that alkylidene dihydropyridines, readily prepared from 4-alkylpyridines, behave as soft nucleophiles toward a range of α,β-unsaturated ketones under the influence of silyl Lewis acids to give the products of conjugate addition. In contrast to existing methods, which use strongly basic pyridylic anions, this reaction tolerates a wide array of functional groups, providing access to useful heterocyclic scaffolds.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Practical and efficient large-scale preparation of 4-methylnicotinic acid

An efficient process for the large-scale synthesis of 4-methylnicotinic acid is developed. The synthetic route utilized 2,6-dichloro-4-methylnicotinonitrile as the starting material, which was commercially available. The key step in the sequence was the reductive dechlorination in the presence of zinc and ammonia to provide an intermediate which was hydrolyzed to the described acid. The reaction parameters optimization and improvement of purification are also presented. This approach, suitable for batch processing, is of interest basically to research laboratories and also to suppliers in the research and fine chemicals market.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof:wherein Y1 is of formula (?) or formula (y):Ring Y is a 5- to 6-membered heteroaryl ring; and V4, V5, Rx, x, y, and n are as defined herein. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

AZAINDENOISOQUINOLINE TOPOISOMERASE I INHIBITORS

The invention described herein pertains to substituted azaindenoisoquinoline compounds, in particular 7-, 8-, 9-, and 10-azaindenoisoquinoline compounds, which are inhibitors of topoisomerase I, processes and intermediates for their syntheses, pharmaceutical compositions of the compounds, and methods of using them in the treatment of cancer.

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 practical and cost-efficient, one-pot conversion of aldehydes into nitriles mediated by 'activated DMSO'

Participation of activated DMSO in the one-pot transformation of aldehydes to nitriles has been described by reacting aldehydes with NHHHCl in DMSO in the absence of any added base or catalyst. The method is applicable to access a wide range of aromatic, heterocyclic, and aliphatic nitriles, in which only water is a byproduct. A straightforward and practical procedure is demonstrated on a multigram scale. Georg Thieme Verlag Stuttgart - New York.

Facile and efficient synthesis of 4-alkyl derivatives of 3-carbamoyl- and 3,5-dicarbamoylpyridines as nicotinamide mimetics

Nicotinamide plays a key role in many biological processes and, as a consequence, its derivatives could be attractive for the synthesis of biologically active compounds. Here a rapid and efficient way of preparing alkyl derivatives of nicotinamide, precisely, 4-alkyl-3-carbamoylpyridine and 4-alkyl-3,5-dicarbamoylpyridine is reported. The synthetic route developed adopts mild reaction conditions and produces target compounds in higher yields compared with methods described in literature. Georg Thieme Verlag Stuttgart · New York.

SOLUBLE FORMS OF INCLUSION COMPLEXES OF HISTONE DEACETYLASE INHIBITORS AND CYCLODEXTRINS, THEIR PREPARATION PROCESSES AND USES IN THE PHARMACEUTICAL FIELD

The invention relates to the preparation of soluble forms of complexes of histone deacetylase inhibitors and cyclodextrins. The preparation process involves the formation of inclusion complexes with cyclodextrins with the aid of microwaves. Their use is in the pharmaceutical field.

Total synthesis of (-)-normalindine via addition of metalated 4-methyl-3-cyanopyridine to an enantiopure sulfinimine

A concise total asymmetric synthesis of the tetrahydronaphthyridine alkaloid (-)-normalindine has been accomplished via the addition of a laterally metalated 4-methyl-3-cyanopyridine to a sulfmimine (N-sulfmyl imine) as the key step.