144374-53-8

Basic information

• Product Name: (E)-tert-Butyl 3-(4-formylphenyl)acrylate
• Synonyms: (E)-tert-Butyl 3-(4-formylphenyl)acrylate
• CAS NO: 144374-53-8
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.27504
• Mol File: 144374-53-8.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerated.
• CAS DataBase Reference: (E)-tert-Butyl 3-(4-formylphenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-tert-Butyl 3-(4-formylphenyl)acrylate(144374-53-8)
• EPA Substance Registry System: (E)-tert-Butyl 3-(4-formylphenyl)acrylate(144374-53-8)

Safety Data

• Hazardous Substances Data: 144374-53-8(Hazardous Substances Data)

Usage

Description

(E)-tert-Butyl 3-(4-formylphenyl)acrylate, with the molecular formula C15H20O3, is a chemical compound that belongs to the class of tert-butyl esters. It is derived from 4-formylcinnamic acid and is characterized by its yellow, liquid appearance and a sweet, floral odor. (E)-tert-Butyl 3-(4-formylphenyl)acrylate is predominantly utilized in the realm of organic synthesis and material science, serving as a fundamental building block for the creation of a diverse array of organic compounds and polymers.

Uses

Used in Organic Synthesis:
(E)-tert-Butyl 3-(4-formylphenyl)acrylate is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable asset in the development of new molecules with potential applications in various industries.
Used in Material Science:
In the field of material science, (E)-tert-Butyl 3-(4-formylphenyl)acrylate is employed as a component in the production of polymers. Its incorporation into polymer structures can lead to the creation of materials with enhanced properties, such as improved strength, flexibility, or chemical resistance.
Used in Pharmaceutical Industry:
(E)-tert-Butyl 3-(4-formylphenyl)acrylate may also find applications in the pharmaceutical industry, where it can be used as a starting material for the synthesis of novel drug candidates. Its reactivity and structural diversity make it a promising candidate for the development of new therapeutic agents.
Used in Chemical Research:
Due to its unique chemical properties, (E)-tert-Butyl 3-(4-formylphenyl)acrylate is also used in academic and industrial research settings. It serves as a model compound for studying various reaction mechanisms and exploring new synthetic methodologies.
Precautions:

Upstream product

• 1663-39-4 tert-Butyl acrylate 
• 1122-91-4 4-bromo-benzaldehyde 
• 623-27-8 terephthalaldehyde, 
• 59159-39-6 (tert-butoxycarbonylmethyl)triphenylphosphonium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 

Downstream Products

• 1174299-12-7 4-[4-(2-tert-Butoxycarbonyl-vinyl)-phenyl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 882507-18-8 3-{4-[3-(3,4-difluoro-phenyl)-3-oxo-propenyl]-phenyl}-acrylic acid tert-butyl ester 
• 926293-63-2 4-[4-(2-tert-butoxycarbonylvinyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 

Relevant articles and documents

Syntheses and catalytic activities of Pd(II) dicarbene and hetero-dicarbene complexes

A series of palladium(II) complexes (1-6) bearing cis-chelating homo-dicarbene ligands with varying alkyl bridges (C1-C3) and N-heterocyclic backbones (imidazole and benzimidazole) have been synthesized by reaction of Pd(OAc)2 with the respective diazolium bromides (A·2HBr - F·2HBr) in DMSO. A comparative catalytic study employing aryl chlorides in the Mizoroki-Heck reaction revealed the superiority of methylene- and propylene-bridged dibenzimidazolin-2-ylidenes over their imidazole-derived analogues. Based on these results, two new propylene-bridged hetero-dicarbene complexes (7 and 8) were designed containing a mixed benzimidazole/imidazole- derived NHC-donor set. Notably, both complexes outperformed their homo-dicarbene analogues, which may be due to the electronic asymmetry induced by hetero-dicarbene ligands. The molecular structures of complex 6 and 8 are also presented.

Mono- and dinuclear palladium(II) complexes incorporating 1,2,3-triazole-derived mesoionic carbenes: syntheses, solid-state structures and catalytic applications

Two 1,2,3-triazole-derived monocationic salts 3 and 4 bearing N-aryl wingtips were prepared using copper-catalyzed “click” reactions followed by alkylations with iodomethane. Employing a silver–carbene transfer method, two dinuclear palladium(II) complexes of triazolin-5-ylidenes (5/6) were obtained, the former of which has been reported previously. Bridge-cleavage reaction of 5 as a representative with PPh3 yielded cis-configured mesoionic carbene/phosphine hybrid complex cis-7 and homoleptic bis(phosphine) complex 8, suggesting the presence of a ligand exchange process. In contrast, bridge breakages of 5/6 with pyridine cleanly afforded PEPPSI-type complexes 9 and 10 in near quantitative yields. Finally, all complexes were exploited to catalyze Mizoroki–Heck coupling reactions with aryl bromides as the substrates, and PEPPSI-type complex 9 was found to be the best performer generally giving good to excellent yields.

Self-assembled Pd nanoparticle-containing ionic liquid: Efficient and reusable catalyst for the Heck reaction in water

A self-assembled Pd nanoparticle-containing ionic liquid as metal–organic polymer was successfully prepared. The structure of the catalyst was characterized using Fourier transform infrared and 1H NMR spectroscopies, scanning electron microscopy and elemental analysis. The catalyst was effectively employed in the palladium-catalyzed Heck reaction in water as a green solvent. Moreover, due to its stability the catalyst can be recovered simply and effectively and reused nine times without much loss of activity.