3156-52-3

Basic information

• Product Name: 3-(2-NITROETHENYL)PYRIDINE
• Synonyms: 2-(3-PYRIDYL)-1-NITROETHYLENE;3-(2-NITROVINYL)PYRIDINE;3-(2-NITROETHENYL)PYRIDINE;Nitroethenylpyridine;3-(2-Nitrovinyl)pyridine 2-(3-Pyridyl)-1-nitroethylene;3-[(E)-2-Nitrovinyl]pyridine;(E)-3-(2-Nitrovinyl)pyridine;2-(pyridyl-3)-1-nitroethene
• CAS NO: 3156-52-3
• Molecular Formula: C₇H₆N₂O₂
• Molecular Weight: 150.13
• Mol File: 3156-52-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 142°C
• Boiling Point: 278.9°C at 760 mmHg
• Flash Point: 122.5°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 0.00704mmHg at 25°C
• Refractive Index: 1.61
• PKA: 3.31±0.11(Predicted)
• CAS DataBase Reference: 3-(2-NITROETHENYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-NITROETHENYL)PYRIDINE(3156-52-3)
• EPA Substance Registry System: 3-(2-NITROETHENYL)PYRIDINE(3156-52-3)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1325
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 3156-52-3(Hazardous Substances Data)

Usage

General Description

3-(2-Nitroethenyl)pyridine (NEP) is a chemical compound that belongs to the class of organic compounds known as pyridines and derivatives. Pyridines are compounds containing a pyridine ring, which is a six-member aromatic heterocycle, non-planar ring with five carbon atoms and one nitrogen atom. NEP has a strong, characteristic odor and is a yellowish, oily liquid at room temperature. It can react with oxidizing agents, acids and bases producing harmful by-products. 3-(2-NITROETHENYL)PYRIDINE is typically used in laboratories for research and development purposes, and its hazardous nature requires it to be handled with care, following specific safety instructions. As it is not widely used industrially or in common consumer products, its environmental and health effects are not well-documented.

InChI:InChI=1/C7H6N2O2/c10-9(11)5-3-7-2-1-4-8-6-7/h1-6H/b5-3+

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 75-52-5 nitromethane 
• 101861-30-7 rac-2-nitro-1-(pyridin-3-yl)ethan-1-ol 

Downstream Products

• 1016169-35-9 3-[3-(4-chloro-phenyl)-1-phenyl-1H-pyrazole-4-yl]-pyridine 
• 1093348-65-2 C₁₄H₁₆N₂O₅ 
• 1321508-43-3 C₁₈H₁₈N₂ 
• 1321508-51-3 3-(1-benzyl-2,5-diphenyl-1H-pyrrol-3-yl)pyridine 
• 1321508-61-5 3-(1-benzyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)pyridine 
• 1321508-62-6 3-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)pyridine 
• 1341160-75-5 3-methoxycarbonyl-3-[2-nitro-1-(3-pyridyl)ethyl]-4-phenyl-2-pyrrolidone 
• 1439359-08-6 (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate 
• 1621003-23-3 3-((3R,4R,5R)-5-(4-chlorophenyl)-2,5-dimethyl-4-nitropyrazolidin-3-yl)pyridine 

Relevant articles and documents

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: Controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams

An asymmetric intermolecular reaction between enals and nitroalkenes to yield δ-nitroesters has been developed, catalyzed by a novel chiral N-heterocyclic carbene. Key to this work was the development of a catalyst that favors the δ-nitroester pathway over the established Stetter pathway. The reaction proceeds in high stereoselectivity and affords the previously unreported syn diastereomer. We also report an operationally facile two-step, one-pot procedure for the synthesis of δ-lactams.

A convenient 1,3-dipolar cycloaddition approach to pyridylpyrroles

A variety of 2-, 3-, and 4-pyridylpyrroles were synthesized in good to excellent yields via the 1,3-dipolar cycloaddition of symmetrical and unsymmetrical muenchnones and nitroalkenes. The unsymmetrical muenchnones show moderate to excellent regioselectiv