4714-25-4

Basic information

• Product Name: 1-nitro-2-(2-phenylethenyl)benzene
• CAS NO: 4714-25-4
• Molecular Formula: C₁₄H₁₁NO₂
• Molecular Weight: 225.2426
• Mol File: 4714-25-4.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 370.3°C at 760 mmHg
• Flash Point: 173.1°C
• Density: 1.22g/cm³
• Vapor Pressure: 2.38E-05mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: 1-nitro-2-(2-phenylethenyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitro-2-(2-phenylethenyl)benzene(4714-25-4)
• EPA Substance Registry System: 1-nitro-2-(2-phenylethenyl)benzene(4714-25-4)

Safety Data

• Hazardous Substances Data: 4714-25-4(Hazardous Substances Data)

Usage

Type of compound

Nitroalkene (contains a nitro group and an alkene functional group)

Usage

Precursor in organic synthesis, production of pharmaceuticals and fine chemicals

Physical state

Yellow, crystalline solid at room temperature

Solubility

Insoluble in water, soluble in organic solvents

Reactivity

Known as a Michael acceptor, can undergo various types of chemical reactions to form new compounds

Safety concerns

Potential toxicological and ecological effects, should be handled and used in a controlled environment

Upstream product

• 110-89-4 piperidine 
• 56-23-5 tetrachloromethane 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 100-52-7 benzaldehyde 
• 110-86-1 pyridine 
• 850815-07-5 α,α'-dibromo-2-nitro-bibenzyl 
• 52208-62-5 (Z)-2-nitrostilbene 
• 5345-40-4 2-nitro-α-phenylcinnamic acid 
• 42497-88-1 4-(4-nitrophenylsulfonylmethyl)benzene 
• 552-89-6 2-nitro-benzaldehyde 
• 100-51-6 benzyl alcohol 
• 64-17-5 ethanol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 13066-19-8 2-(2-phenylethenyl)benzenamine 
• 4264-29-3 (E)-2-nitrostilbene 
• 5697-85-8 2-(2-phenylethyl)aniline 
• 948-65-2 2-phenyl-indole 
• 909297-33-2 (E)-2-(((2-styrylphenyl)amino)methyl)phenol 
• 1859-39-8 2-phenyl-N-hydroxyindole 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 89346-69-0 2-(2-phenylethyl)benzenediazonium tetrafluoroborate 
• 776-35-2 9,10-dihydrophenanthrene 
• 35010-10-7 1-(2-nitrophenyl)-2-phenylethane-1,2-dione 
• 1969-74-0 2-phenylisatogen 
• 923291-65-0 4-methyl-N-(2-styryl-phenyl)-selenobenzimidic acid phenyl ester 
• 923291-66-1 (Z)-phenyl N-(2-styrylphenyl)ethaneselenoimidate 

Relevant articles and documents

Synthesis, characterization, structure and catalytic activity of (NNN) tridentate azo-imine nickel(II), palladium(II) and platinum(II) complexes

The newly designed tridentate ligand, 2,2′-(bisdiamino)azobenzene, H2L, 1 derived from the oxidative coupling of o-phenylenediamine in presence of NaOH base, upon reaction with Ni(II), Pd(II) and Pt(II) separately in methanol yielded [(HL)Ni(PPh3)]ClO4, 2, [(HL)Pd(PPh3)]ClO4, 3 and [(L)Pt(PPh3)], 4 which were characterized by spectral data and authenticated by single crystal X-ray diffraction of 1-4. The diffraction analysis revealed that the ligand binds the metals (Ni(II), Pd(II)) in monoanionic and Pt(II) in dianionic tridentate (N,N,N) fashion offering distorted square planar geometry where fourth position is occupied by one PPh3group. One ClO4-ion satisfies the charge of the former aggregate [(HL)Ni(PPh3)]+and [(HL)Pd(PPh3)]+. Suzuki and Heck coupling reactions were carried out, in presence of air and moisture, using [(HL)Pd(PPh3)]ClO4, 3 as catalysts for a variety of substrates.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

Synthesis, characterization, crystal structure and catalytic activity of amido azo palladium(II) complex

Abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline, 1 has been synthesized by the reaction between 2,2′-diaminoazobenzene and benzyl chloride in presence of K2CO3. This ligand was reacted with Na2[PdCl4] in methanol to give the new Pd(II) complex?2. Both the ligand and complex were characterized by usual spectroscopic techniques. Furthermore, the solid-state structure of complex 2 was determined using single crystal X-ray diffraction analysis. It revealed that the ligand binds with Pd(II) in dianionic tridentate (N,N,N) fashion offering distorted square planar geometry where fourth position is occupied by one phosphine ligand. The performance of the Pd(II) phosphine complex as catalyst was evaluated in the homogenous Suzuki and Heck reactions under mild conditions in presence of air and moisture. The Pd(II) complex showed good catalytic activities for the coupling of several aryl halides (iodides and bromides) with phenyl boronic acid and styrene providing excellent yields. After catalytic reactions, the catalyst has been recovered by simple chromatographic separation and reused for next reaction and its activity checked up to three cycles without sufficient loss. Graphic abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline and its corresponding palladium(II) complex were synthesized and structurally characterized. The neutral palladium(II) amido complex with phosphine as ancillary ligand was formed through two amino proton elimination from ligand precursor. The newly synthesized Palladium(II) complex acts as potential catalyst toward C–C bond formation for a variety of substrate under mild conditions in presence of air and moisture.[Figure not available: see fulltext.].