27019-24-5

Basic information

• Product Name: (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate
• Synonyms: (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate
• CAS NO: 27019-24-5
• Molecular Weight: 314.254
• EINECS: -0
• Mol File: 27019-24-5.mol

Chemical Properties

• CAS DataBase Reference: (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate(27019-24-5)
• EPA Substance Registry System: (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate(27019-24-5)

Safety Data

• Hazardous Substances Data: 27019-24-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate is used as a raw material for the synthesis of various pharmaceutical intermediates and organic compounds. Its unique chemical structure makes it a promising candidate for the development of anti-cancer and anti-inflammatory drugs.
Used in Materials Science:
(E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate is used in materials science for the development of new materials with specific properties. Its chemical structure allows for the creation of novel materials with potential applications in various industries.
It is important to handle and use (E)-4-nitrophenyl 3-(4-nitrophenyl)acrylate with caution, as it may be harmful if ingested, inhaled, or comes into contact with the skin.

Upstream product

• 100-02-7 4-nitro-phenol 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 77614-06-3 C₁₅H₁₀ClNO₄ 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 105650-19-9 C₁₆H₁₃NO₄ 
• 71255-82-8 C₁₆H₁₃NO₅ 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 22440-58-0 (E)-4-nitrocinnamic acid chloride 
• 619-89-6 p-nitrocinnamic acid 

Downstream Products

• 261519-71-5 C₁₂H₉N₃O₃ 
• 380539-93-5 benzyl 4-nitrocinnamate 
• 56310-46-4 4-Nitro-zimtsaeure-(4-chlor-phenylester) 
• 77614-06-3 C₁₅H₁₀ClNO₄ 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 105650-19-9 C₁₆H₁₃NO₄ 
• 71255-82-8 C₁₆H₁₃NO₅ 
• 100-02-7 4-nitro-phenol 
• 1009839-17-1 C₁₅H₁₂N₄O₄ 
• 112601-99-7 (E)-3-(benzoyl 4-nitro)-1-(piperidin-1-yl)prop-2-en-1-one 
• 1041868-01-2 (E)-3-(4-nitrophenyl)-1-(1,3-oxazinan-3-yl)prop-2-en-1-one 
• 351027-13-9 N-(p-nitrocinnamoyl)imidazole 
• 1041867-96-2 C₁₉H₁₄N₂O₃ 
• 60573-41-3 (E)-3-(4-nitrophenyl)-N-phenylacrylamide 

Relevant articles and documents

Isothiourea-catalysed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters

A protocol for the isothiourea-catalysed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters using Hantzsch ester has been developed. Good to excellent yields are observed using α,β-unsaturated aryl esters bearing electron-withdrawing β-subs

DIAMINE, POLYMER, LIQUID CRYSTAL ALIGNING AGENT, LIQUID CRYSTAL ALIGNMENT FILM, AND LIQUID CRYSTAL DISPLAY ELEMENT

A diamine characterized by being represented by formula (1) (wherein X1 represents a single bond or an alkylene group having 1 to 6 carbon atoms (wherein non-adjacent -CH2- groups in the alkylene group may be independently substituted by an ether bond, an

Structure-reactivity correlations in nucleophilic displacement reactions of Y-substituted-phenyl X-substituted-cinnamates with Z-substituted-phenoxides

Second-order rate constants (kN) have been measured spectrophotometrically for the nucleophilic displacement reactions of 4-nitrophenyl X-substituted-cinnamates (4a-4e) and Y-substituted-phenyl cinnamates (5a-5e) with Z-substituted-phenoxide anions in 80 mol % H2O/20 mol % DMSO at 25.0 ±0.1 °C. The Hammett plot for the reactions of 4a-4e with 4-chlorophenoxide (4-ClPhO.) consists of two intersecting straight lines, which might be taken as a change in the rate-determining step (RDS). However, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of substrates possessing an electron-withdrawing group in the cinnamoyl moiety through resonance interactions, since the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 0.89 and r = 0.58. The Bronsted-type plot for the reactions of 4-nitrophenyl cinnamate (4c) with Z-substituted-phenoxides is linear with βnuc = 0.76. The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (5a-5d) with 4-chlorophenoxides (4-ClPhO.) is also linear with βlg =.0.72. The Hammett plot correlated with σ-. constants for the reactions of 5a-5d results in a much better linear correlation than that correlated with σo constants, indicating that a partial negative charge develops on the O atom of the leaving aryloxide. Thus, the reactions have been concluded to proceed through a concerted mechanism.

The α-effect in nucleophilic substitution reactions of Y-substituted-Phenyl X-substituted-cinnamates with Butane-2,3-dione monoximate

Second-order rate constants (kOx-) have been measured spectrophotometrically for nucleophilic substitution reactions of 4-nitrophenyl X-substituted-cinnamates (7a-7e) and Y-substituted-phenyl cinnamates (8a-8e) with butane-2,3-dione monoximate (Ox-) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The Hammett plot for the reactions of 7a-7e consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linearity with ρX = 0.85 and r = 0.58, indicating that the nonlinear Hammett plot is not due to a change in the rate-determining step but is caused by resonance stabilization of the ground state (GS) of the substrate possessing an electron-donating group (EDG). The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (8a-8e) is linear with βlg = - 0.64, which is typical of reactions reported previously to proceed through a concerted mechanism. The a-nucleophile (Ox-) is more reactive than the reference normalnucleophile (4-ClPhO-). The magnitude of the α-effect (i.e., the kOx-/k4-ClPhO- ratio) is independent of the electronic nature of the substituent X in the nonleaving group but increases linearly as the substituent Y in the leaving group becomes a weaker electron-withdrawing group (EWG). It has been concluded that the difference in solvation energy between Ox- and 4-ClPhO - (i.e., GS effect) is not solely responsible for the α-effect but stabilization of transition state (TS) through a cyclic TS structure contributes also to the Y-dependent a-effect trend (i.e., TS effect).

Influence of electronically and sterically tunable cinnamate ligands on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine) palladium(0) olefin complexes

A detailed study of the influence of electronic and steric characteristics of cinnamic acid esters on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine)palladium(0) cinnamic acid ester complexes is presented (51 different new complexes included). These complexes show a dynamic behavior on the NMR spectroscopic time scale. Therefore, the rotational barriers of the olefin about the metalolefin bond as well as the dissociation entropy and enthalpy of the olefin and the dissociation mechanism could be determined. These findings are interpreted together with the NMR spectroscopic, IR spectroscopic, and X-ray structural data (7 new structures included) concerning the influence of the different olefin ligands on the complex properties by means of Hammett plots. DFT calculations were performed to support the mechanistic conclusions.

Cinnamoyl inhibitors of tissue transglutaminase

(Figure Presented) Transglutaminases (TGases) catalyze the intermolecular cross-linking of certain proteins and tissue TGases (TG2) are involved in diverse biological processes. Unregulated, high TGase activities have been implicated in several physiological disorders, but few reversible inhibitors of TG2 have been reported. Herein, we report the synthesis of a series of novel trans-cinammoyl derivatives, discovered to be potent inhibitors of guinea pig liver transglutaminase. The most effective inhibitors evaluated can be sorted into two subclasses: substituted cinnamoyl benzotriazolyl amides and the 3-(substituted cinnamoyl)pyridines, referred to more commonly as azachalcones. Kinetic evaluation of both of these subclasses revealed that they display reversible inhibition and are competitive with acyl donor TGase substrates at IC50 values as low as 18 μM. An analysis of structure - activity relationships within these series of inhibitors permitted the identification of potentially important binding interactions. Further testing of some of the most potent inhibitors demonstrated their selectivity for TG2 and their potential for further development.

Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives

In this work, we report the synthesis and the antimycobacterial evaluation of new trans-cinnamic acid derivatives of isonicotinic acid series (5) and benzoic acid series (6), designed by exploring the molecular hybridization approach between isoniazid (1)

CINNAMOYL INHIBITORS OF TRANSGLUTAMINASE

A compound of Formula, (I) or Formula: (II)

Diamine and acid anhydride

The present invention provides a novel diamine and a novel acid anhydride which are applicable for a polyimide and includes a cinnamoyl group or a derived cinnamoyl group. The novel diamines and acid anhydrides have photo-reactivity and heat-reactivity inherent to the cinnamoyl group.

MECHANISM OF ESTER AMINOLYSIS IN APROTIC MEDIA AND SPECIFIC SOLVENT EFFECTS

The n-butylaminolysis of nitro-substituted 4'-nitrophenyl benzoates and cinnamates as well as of phenylacetates in aprotic solvents is governed by a kinetic law implying higher order terms in nucleophile.It is shown that the attacking nucleophile forms a n-? type molecular complex with the substrate before reaching the transition state in the subsequent kinetic step.This molecular complex is a true reaction intermediate as evidenced by the observed negative activation enthalpy.Other nucleophile molecules intervene as general base catalysts.Tertiary amines also catalyse the reaction.Their catalytic activity is linearly related to their hydrogen bond forming ability and it is not a direct function of their proton basicity.By varying the nucleophile structure, an excellent Broensted relationship could be obtained for the first time in aprotic media, the β of which confirms that the catalytic collapse of tetrahedral intermediate is the rate determining step.The reaction of cinnamates turns out to be less sensitive to structural changes of the substrate than is the reaction of benzoates as shown by the corresponding Hammet ? values.The electronic effects of 2-nitro groups are strongly solvent dependent.Once more, it is established that whenever specific solvent effects (?-donor or n-donor ability) are present, they dominate the overall effect.A general reaction mechanism is proposed which not only explains the various roles played by the nucleophile but also accounts successfully for the great variety of kinetic schemes observed in aprotic media.