4513-92-2

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethylpyrrole-2-carbonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into the molecular structures of drugs. It contributes to the development of new medications with improved therapeutic properties and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-Dimethylpyrrole-2-carbonitrile is utilized as a building block in the creation of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds enhances their effectiveness in controlling pests and weeds, thereby improving crop yields and quality.
Used in Material Science:
3,5-Dimethylpyrrole-2-carbonitrile is employed in the development of advanced materials, including polymers and composites, due to its unique chemical structure and properties. It can be used to modify the properties of materials, such as their stability, conductivity, and mechanical strength, for various applications in different industries.
Used in Research and Development:
3,5-Dimethylpyrrole-2-carbonitrile is also used in research and development activities to explore its potential applications and properties further. Scientists and researchers use 3,5-DIMETHYLPYRROLE-2-CARBONITRILE to investigate new chemical reactions, synthesis methods, and its interactions with other molecules, paving the way for the discovery of novel applications and technologies.

InChI:InChI=1/C7H8N2/c1-5-3-6(2)9-7(5)4-8/h3,9H,1-2H3

Upstream product

• 61295-92-9 methyl 2-cyano-2-hydroxyiminoacetate 
• 123-54-6 acetylacetone 
• 1118-66-7 4-Aminopent-3-en-2-one 
• 26187-29-1 2,5-dimethyl-1H-pyrrole-3-carbonitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 140-29-4 phenylacetonitrile 
• 484698-44-4 tert-butyl-2,4-dimethyl-1H-pyrrole-1-carboxylate 
• 59132-86-4 N-(1-methyl-3-oxo-1-butenyl)glycinonitrile 
• 3849-21-6 ethyl cyanoglyoxylate-2-oxime 

Downstream Products

• 467470-43-5 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carbonitrile 
• 524035-96-9 3,5-dimethyl-4-formyl-1H-pyrrole-2-carbonitrile 
• 467470-45-7 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxamide 
• 26187-28-0 2,4-dimethyl-1H-pyrrole-3-carbonitrile 
• 26187-29-1 2,5-dimethyl-1H-pyrrole-3-carbonitrile 

Relevant academic research and scientific papers

Discovery of n-phenyl-4-(1h-pyrrol-3-yl)pyrimidin-2-amine derivatives as potent mnk2 inhibitors: Design, synthesis, sar analysis, and evaluation of in vitro anti-leukaemic activity

Background: Aberrant expression of eukaryotic translation initiation factor 4E (eIF4E) is common in many types of cancer including acute myeloid leukaemia (AML). Phosphorylation of eIF4E by MAPK-interacting kinases (Mnks) is essential for the eIF4E-mediated oncogenic activity. As such, the pharmacological inhibition of Mnks can be an effective strategy for the treatment of cancer. Methods: A series of N-phenyl-4-(1H-pyrrol-3-yl)pyrimidin-2-amine derivatives was designed and synthesised. The Mnk inhibitory activity of these derivatives as well as their anti-proliferative activity against MV4-11 AML cells was determined. Results: These compounds were identified as potent Mnk2 inhibitors. Most of them demonstrated potent anti-proliferative activity against MV4-11 AML cells. The cellular mechanistic studies of the representative inhibitors revealed that they reduced the level of phosphorylated eIF4E and induced apoptosis by down-regulating the anti-apoptotic protein myeloid cell leukaemia 1 (Mcl-1) and by cleaving poly(ADP-ribose)polymerase (PARP). The lead compound 7k possessed desirable pharmacokinetic properties and oral bioavailability. Conclusion: This work proposes that exploration of the structural diversity in the context of N-phenyl-4-(1H-pyrrol-3-yl)pyrimidin-2-amine would offer potent and selective Mnk inhibitors.

3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

Precursors of 3-pyridylnitrene and 2- and 4-pyrimidinylcarbenes all afford mixtures of 2- and 3-cyanopyrroles on flash vacuum thermolysis, but 3-cyanopyrroles are the first-formed products. 3-Quinolylnitrenes and 4-quinazolinylcarbenes similarly afford 3-cyanoindoles. 2-Pyrimidinylcarbenes rearrange to 3-pyridylnitrenes, but 4-pyrimidinylcarbenes and 4-quinazolinylcarbenes do not necessarily rearrange to the corresponding 3-pyridylnitrenes or 3-quinolylnitrenes. The ring contraction reactions are interpreted in terms of ring opening of either the nitrenes or the diazacycloheptatetraenes to nitrile ylides.

Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate

A copper-mediated direct cyanation of indoles with benzyl cyanide as the cyanide anion surrogate has been achieved. The cascade reaction furnished 3-cyanoindoles under mild reaction conditions in good to excellent yields with various functional groups tolerance.

Unusual oxidation in the course of synthesis of V-confused nickel tetrahydrobilins

TV-confused Tetrahydrobilins rac-16 and rac-17 were prepared to investigate their cyclization directed to the formation of N-confused chlorins. For achieving the desired cyclization the 5'-position of rac-16 respectively rac-17 was activated by an electron withdrawing cyano function and their 2'-positions were blocked by a methyl group. In addition, the insertion of Ni(II) was accomplished for exercising a template effect during the cyclization process, but the formed nickel complexes rac-18 and rac-19 underwent oxidation to yield oxo-tetrahydrobilins rac-20 and rac-21. The Japan Institute of Heterocyclic Chemistry.

Synthesis of cyanopyrroles

Regioselective synthesis of α-cyanopyrroles (vs. α- alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, methyl oximinocyanoacetate was reacted with pentane-2,4-dione in hot acetic acid in the presence of zinc dust to give exclusively 3,5- dimethylpyrrole-2-carbonitrile when the acetic acid was wet; whereas, in glacial acetic acid only methyl 3,5-dimethylpyrrole-2-carboxylate was isolated (~40% yield).

THE REACTION OF β-AMINOENONES WITH α-AMINO DERIVATIVES. SYNTHESIS OF 2-FUNCTIONALIZED PYRROLES

β-Aminoenones react with ethyl glycinate, α-aminoacetonitrile and α-aminoacetamide hydrochlorides leading to 2-fuctionalized pyrroles.Although the trans-amination is a high-yield process, the transformation of the intermediate, in both basic or thermally