5153-73-1

Basic information

• Product Name: 1-(4-CYANOPHENYL)-2-NITROETHENE
• Synonyms: 1-(4-CYANOPHENYL)-2-NITROETHENE;TRANS-4-(2-NITROETHENYL)BENZONITRILE;TRANS-4-(2-NITROVINYL)BENZONITRILE;(E)-p-(2-Nitrovinyl)benzonitrile;(E)-p-Cyano-beta-nitrostyrene;4-[(E)-2-Nitroethenyl)benzonitrile;E-4-Cyano-beta-nitrostyrene;(E)-4-(2-Nitrovinyl)benzonitrile
• CAS NO: 5153-73-1
• Molecular Formula: C₉H₆N₂O₂
• Molecular Weight: 174.16
• Product Categories: Ethanes/ethenes
• Mol File: 5153-73-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 353.5 °C at 760 mmHg
• Flash Point: 167.6 °C
• Appearance: /
• Density: 1.25
• Vapor Pressure: 3.56E-05mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-(4-CYANOPHENYL)-2-NITROETHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CYANOPHENYL)-2-NITROETHENE(5153-73-1)
• EPA Substance Registry System: 1-(4-CYANOPHENYL)-2-NITROETHENE(5153-73-1)

Safety Data

• Statements: 20/21/22
• Safety Statements: 36/37/39
• RIDADR: UN 3439 6.1/PG III
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5153-73-1(Hazardous Substances Data)

Usage

General Description

1-(4-CYANOPHENYL)-2-NITROETHENE is a chemical compound with the molecular formula C9H6N2O2, which falls under the broad category of aromatic homomonocyclic compounds. As suggested by its name, this chemical consists of 4 cyanophenyl group and 2 nitroethene moiety. 1-(4-CYANOPHENYL)-2-NITROETHENE is predominantly used in research and industrial applications. Its chemical properties including reactivity and polarity are highly influenced by its cyano and nitro functional groups. Like many other organic compounds, it must be handled properly to avoid any harmful effects, as it has not been fully characterized in terms of potential toxicity to human health. It also requires careful storage to maintain its stability and prevent any spontaneous and potentially hazardous chemical reactions.

InChI:InChI=1/C9H6N2O2/c10-7-9-3-1-8(2-4-9)5-6-11(12)13/h1-6H

Upstream product

• 16642-94-7 (E)-4-cyanocinnamic acid 
• 3435-51-6 4-ethenylbenzonitrile 
• 75-52-5 nitromethane 
• 105-07-7 4-cyanobenzaldehyde 
• 20655-58-7 ethyl (E)-4-cyanocinnamate 

Downstream Products

• 1616482-55-3 diethyl 3-(4-cyanophenyl)-4-nitro-5-(4-nitrophenyl)pyrrolidine-2,2-dicarboxylate 
• 1620445-81-9 (E)-N-(3-(4-cyanophenyl)allyl)-N-methylacetamide 
• 56527-23-2 4-(1H-1,2,3-triazol-4-yl)benzonitrile 
• 172348-86-6 tert-butyl N-[2-(4-cyanophenyl)ethyl]carbamate 
• 791839-12-8 [2-(4-carbamimidoyl-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 132224-93-2 [(4-cyanophenyl)methyl]methanamine 
• 1008520-19-1 4-(1-Benzyl-7-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-benzamide 
• 1008520-22-6 4-[7-Oxo-1-(3,4,5-trimethoxy-benzyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-benzamide 

Relevant articles and documents

Metal-free Synthesis of β-Nitrostyrenes via DDQ-Catalyzed Nitration

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Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.

Preparation method of nitroolefin derivative with nitrate as nitro source

The invention relates to a nitroolefin derivative with nitrate as nitro source and a preparation method thereof. Under the atmosphere of nitrogen, an olefin compound, nitrate, trimethylchlorosilane (TMSC1) and copper salt are stirred in acetonitrile at 0-30 DEG C; in addition, the reaction degree is monitored by using a TLC point plate; after the olefin compound is completely consumed, alkali is added to an obtained mixture to be stirred for 20-30 min; then after a solvent is removed from an obtained mixture by using a rotary evaporator, the nitroolefin derivative can be obtained through silicagel column purification. Compared with the prior art, the nitroolefin derivative with the nitrate as the nitro source, provided by the invention, has the advantages of mild reaction condition, high yield, high E type selectivity and the like.