111971-56-3

Basic information

• Product Name: 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE
• Synonyms: 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE;6-amino-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile;3,5-Pyridinedicarbonitrile, 6-amino-1,2-dihydro-2-thioxo-
• CAS NO: 111971-56-3
• Molecular Formula: C₇H₄N₄S
• Molecular Weight: 176.2
• Mol File: 111971-56-3.mol

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 270.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• PKA: 4.69±0.70(Predicted)
• CAS DataBase Reference: 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE(111971-56-3)
• EPA Substance Registry System: 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE(111971-56-3)

Safety Data

• Hazardous Substances Data: 111971-56-3(Hazardous Substances Data)

Usage

General Description

2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE is a chemical compound with the molecular formula C6H4N4S. It is a pyridine derivative with two amino groups and a mercapto group attached to the pyridine ring, as well as two cyano groups attached to the carbon atoms in positions 3 and 5. 2-AMINO-6-MERCAPTOPYRIDINE-3,5-DICARBONITRILE is commonly used in organic synthesis and pharmaceutical research, and it has potential applications in the development of new drugs and bioactive molecules. Its unique structure and functional groups make it a versatile building block for the synthesis of various compounds with biological activity. Additionally, it has been studied for its potential antimicrobial and antiproliferative properties, making it a promising candidate for further research and development in the fields of medicine and healthcare.

Upstream product

• 50-00-0 formaldehyd 
• 7357-70-2 Cyanothioacetamide 
• 107-91-5 cyanoacetic acid amide 
• 112124-35-3 sodium 6-amino-3,5-dicyanopyridine-2-thiolate 
• 134836-45-6 2,6-diamino-4(2H)-thiopyran-3,5-dicarbonitrile 
• 123-06-8 Ethoxymethylenemalononitrile 
• 109-77-3 malononitrile 

Relevant articles and documents

A simple one-pot synthesis of new 4-unsubstituted 2-oxo(thioxo)-1,2-dihydropyridine-3-carbonitriles, -3-carboxamides, and -3-carboxylic acid esters and 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitriles

One-pot condensations of formaldehyde with CH acids and enamines afforded new 4-unsubstituted derivatives of 2-oxo(thioxo)-1,2-dihydropyridine-3-carbonitrile, 2-oxo(thioxo)-1,2-dihydropyridine-3-carboxamide, ethyl 2-oxo(thioxo)-1,2-dihydropyridine-3-carboxylate, and 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, which were subjected to alkylation.

3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells

A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1–5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI50of 50–250?nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket.

NITRILES IN ORGANIC SYNTHESIS: SYNTHESIS OF NEW POLYFUNCTIONALLY SUBSTITUTED PYRIDINE AND PYRIDOPYRIDINE DERIVATIVES

A variety of polyfunctionally substituted pyridines could be prepared by reacting malononitrile with a variety of active methylene reagents. Some of the synthesized compounds could be converted into pyridopyridines via hydrolysis and recyclization in the presence of an acid catalyst.

STUDIES WITH POLYFUNCTIONALLY SUBSTITUTED HETEROCYCLES: SYNTHESIS OF NEW THIOPYRANS, PYRIDINES AND PYRANS AND THEIR FUSED DERIVATIVES WITH OTHER RINGS SYSTEMS

The thiopyran derivative 3 was obtained from the reaction of cyanothioacetamide 2 with formaldehyde and malononitrile.Compound 3 is converted into the pyridinethione 5 on long reflux in ethanolic triethylamine solution.The pyridinethione 7 is produced from reaction of 2 with acetaldehyde and malononitrile.Compound 7 afforded 9 on reaction with 1a, R = Ph, and 11 on treatment with phenacyl bromide.The pyran derivative 13, formed in analogous manner from 12, afforded 19 on further reaction with formaldehyde and malononitrile, and 22 on reaction with acetic anhydride.Whereas the pyranopyrazole 27 is formed from 25a on reaction with formaldehyde and malononitrile in refluxing ethanol, 25b afforded only 28 an similar treatment.Similarly, thiazolopyridine derivative 30 and phthalazine 32 were formed from 29 and 31 respectively.

CYCLIZATION OF NITRILES. XXV. SYNTHESIS AND REACTIONS OF CHALCOGEN-CONTAINING 6-AMINO-3,5-DICYANOPYRIDINES

Methods were developed for the synthesis of 6-amino-3,5-dicyano-2(1H)-pyridinethiones and the corresponding selenones by the reaction of β-alkoxy- or β-aminomethylenemalonitriles with cyanothio(seleno)acetamides.The salts of pyridine-2-thiolates are alkylated selectively by halogenoalkanes with the formation of 2-alkylthiopyridines, which were used in the synthesis of 3-aminothienopyridines and quaternized thiazolopyridines.