6443-85-2

Basic information

• Product Name: 3-PYRIDYLACETONITRILE
• Synonyms: PYRIDINE-3-ACETONITRILE;3-PYRIDINEACETONITRILE;3-PYRIDYLACETONITRILE;3-PYRIDYLMETHYL CYANIDE;3-(CYANOMETHYL)PYRIDINE;3-Pyridinylacetonitrile;Pyridine-3-acetonitrile,98%;NSC 83226
• CAS NO: 6443-85-2
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• EINECS: 229-241-1
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;pharmacetical;Building Blocks;C7 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines
• Mol File: 6443-85-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 99-100 °C
• Boiling Point: 101-109 °C1.5 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: very deep yellow/Liquid
• Density: 1.108 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00511mmHg at 25°C
• Refractive Index: n20/D 1.529(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.17±0.10(Predicted)
• Water Solubility: Soluble in alcohol, ether, ketone. Insoluble in water.
• BRN: 111292
• CAS DataBase Reference: 3-PYRIDYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PYRIDYLACETONITRILE(6443-85-2)
• EPA Substance Registry System: 3-PYRIDYLACETONITRILE(6443-85-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6443-85-2(Hazardous Substances Data)

Usage

Description

3-Pyridineacetonitrile, also known as 3-PYRIDYLACETONITRILE, is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by its pyridine ring and nitrile functional group, which contribute to its reactivity and potential applications in chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-PYRIDYLACETONITRILE is used as a reactant for the preparation of 1,7-naphthyridine derivatives, which are known as phosphodiesterase-4 inhibitors. These inhibitors play a crucial role in the treatment of various inflammatory and respiratory conditions, such as chronic obstructive pulmonary disease (COPD) and asthma, by modulating the activity of specific enzymes involved in these diseases.

InChI:InChI=1/C7H6N2/c8-4-3-7-2-1-5-9-6-7/h1-2,5-6H,3H2

Upstream product

• 59020-10-9 3-(tributylstannyl)pyridine 
• 626-55-1 3-Bromopyridine 
• 105-56-6 ethyl 2-cyanoacetate 
• 501-81-5 pyridyl-3-yl-acetic acid 
• 110-86-1 pyridine 
• 75-05-8 acetonitrile 
• 42545-63-1 2-(pyrid-3-yl)acetaldehyde 
• 39931-77-6 pyridin-3-yl-acetic acid ethyl ester 
• 1120-90-7 3-iodopyridine 
• 144205-15-2 C₁₆H₁₆N₄⁽²⁺⁾*2Br^(1-) 
• 135041-78-0 3-Cyanomethyl-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide 
• 130671-08-8 1-(2-Cyano-ethyl)-3-cyanomethyl-pyridinium; bromide 
• 117504-09-3 α-Phenylsulfonyl-3-pyridineacetonitrile 
• 143-33-9 sodium cyanide 

Downstream Products

• 51451-44-6 2-pyridin-3-yl-thioacetamide 
• 6635-88-7 3-(cyanomethyl)pyridine 1-oxide 
• 127667-26-9 2-(Cyano-pyridin-3-yl-methyl)-benzonitrile 
• 144061-50-7 2-(3-pyridylmethyl)-3,6-tetramethylbenzonitrile 
• 144061-51-8 2-(3-pyridylmethyl)-6-methoxy-3-methylbenzonitrile 
• 25230-06-2 3-Pyridylmalononitrile 
• 144061-49-4 2-(3-pyridylmethyl)-3,4,5,6-tetramethylbenzonitrile 
• 119-65-3 isoquinoline 
• 92060-41-8 (Z)-3-phenyl-2-(pyridin-3-yl)acrylonitrile 
• 6529-37-9 4-phenyl-2-(pyridin-3-yl)butyronitrile 
• 144467-13-0 2-(3-Pyridyl)-3-phenyl-5-oxohexanenitrile 
• 5562-24-3 3-Cyanomethyl-1-methyl-pyridinium; iodide 

Relevant articles and documents

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

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.

Tetrazolylhydrazides as selective fragment-like inhibitors of the JumonjiC-domain-containing histone demethylase KDM4A

The JumonjiC-domain-containing histone demethylase 2A (JMJD2A, KDM4A) is a key player in the epigenetic regulation of gene expression. Previous publications have shown that both elevated and lowered enzyme levels are associated with certain types of cancer, and therefore the definite role of KDM4A in oncogenesis remains elusive. To identify a novel molecular starting point with favorable physicochemical properties for the investigation of the physiological role of KDM4A, we screened a number of molecules bearing an iron-chelating moiety by using two independent assays. In this way, we were able to identify 2-(1H-tetrazol-5-yl)acetohydrazide as a novel fragment-like lead structure with low relative molecular mass (Mr=142 Da), low complexity, and an IC50 value of 46.6 μm in a formaldehyde dehydrogenase (FDH)-coupled assay and 2.4 μm in an antibody-based assay. Despite its small size, relative selectivity against two other demethylases could be demonstrated for this compound. This is the first example of a tetrazole group as a warhead in JMJD demethylases. Anchor fragment: To develop non-promiscuous metalloenzyme inhibitors, a metal-complexing acetohydrazide group was integrated in a tetrazolyl fragment, which can be matured into a scaffold to promote further selectivity at the ligand backbone binding site of these emerging drug targets.