4513-92-2

Basic information

• Product Name: 3,5-DIMETHYLPYRROLE-2-CARBONITRILE
• Synonyms: 3,5-DIMETHYLPYRROLE-2-CARBONITRILE;1H-Pyrrole-2-carbonitrile,3,5-dimethyl-(9CI)
• CAS NO: 4513-92-2
• Molecular Formula: C₇H₈N₂
• Molecular Weight: 120.15
• Product Categories: PYRROLIDINE
• Mol File: 4513-92-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 273.6 °C at 760 mmHg
• Flash Point: 103.1 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0.00568mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 3,5-DIMETHYLPYRROLE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYLPYRROLE-2-CARBONITRILE(4513-92-2)
• EPA Substance Registry System: 3,5-DIMETHYLPYRROLE-2-CARBONITRILE(4513-92-2)

Safety Data

• Hazardous Substances Data: 4513-92-2(Hazardous Substances Data)

Usage

General Description

3,5-Dimethylpyrrole-2-carbonitrile is a chemical compound with the molecular formula C7H8N2. It is a substituted pyrrole derivative, which is a heterocyclic compound containing a five-membered ring with four carbon atoms and one nitrogen atom. The compound is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also utilized in the development of materials and in research and development activities. 3,5-Dimethylpyrrole-2-carbonitrile has various chemical and biological properties that make it valuable for a wide range of applications in the pharmaceutical, agricultural, and material science industries.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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).