31930-37-7

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (E)-3-iodoacrylate is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and improving the efficacy of existing medications. Its reactivity in organic reactions, such as Michael addition, Sonogashira coupling, and Heck reaction, allows for the creation of complex molecular structures with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, Ethyl (E)-3-iodoacrylate is utilized as an intermediate for the production of agrochemicals, including pesticides and herbicides. Its involvement in organic synthesis enables the development of effective and targeted chemical solutions for agricultural use, enhancing crop protection and yield.
Used in Flavors and Fragrances Industry:
Ethyl (E)-3-iodoacrylate is employed in the manufacture of flavors and fragrances, where its unique chemical properties contribute to the creation of diverse and complex scents. Its use in this industry allows for the development of novel and innovative fragrances, as well as the enhancement of existing ones.
Safety Considerations:
Due to its flammable nature and potential to cause irritation to the skin, eyes, and respiratory system, proper handling and storage of Ethyl (E)-3-iodoacrylate are essential to prevent potential hazards. Adhering to safety protocols and guidelines ensures the safe use of Ethyl (E)-3-iodoacrylate in various applications.

Upstream product

• 64-17-5 ethanol 
• 6372-02-7 (E)-3-iodoacrylic acid 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 71815-44-6 (E/Z)-3-iodoacrylic acid 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 127915-51-9 ethyl (E)-5-(1-cyclohexen-1-yl)-2-penten-4-ynoate 
• 117552-48-4 E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester 
• 266325-23-9 ethyl (E)-6-phenylhex-2-en-5-ynoate 
• 6032-74-2 diethyl (2E,4E)-2,4-hexadienedioate 
• 342374-97-4 (2E,4E)-(R)-10-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-deca-2,4-dienoic acid ethyl ester 
• 75717-35-0 ethyl (E)-3-(phenylthio)-2-propenoate 
• 66901-42-6 ethyl-(E)-dec-2-en-4-yn-oate 
• 1004981-30-9 C₁₈H₂₁NO₄S 
• 1004981-32-1 ethyl (3E)-5-[(S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-methyl-5-oxo-3-pentenoate 
• 1004981-36-5 C₁₈H₂₃NO₅ 
• 1004981-25-2 ethyl (2E,4R)-5-[(S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-methyl-5-oxo-2-pentenoate 
• 1004981-26-3 ethyl (2E,4S)-5-[(S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-methyl-5-oxo-2-pentenoate 
• 1219835-83-2 ethyl (E)-6-(3-p-tolylprop-2-ynylthio)hex-2-en-4-ynoate 
• 1242165-69-0 ethyl (2E,4Z,8E)-9-phenyl-7-hydroxy-2,4,8-nonatrienoate 

Relevant academic research and scientific papers

Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter

Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.

Diastereo- and Enantioselective Cross-Couplings of Secondary Alkylcopper Reagents with 3-Halogeno-Unsaturated Carbonyl Derivatives

Chiral secondary alkylcopper reagents were prepared from the corresponding alkyl iodides with retention of configuration by an I/Li-exchange using tBuLi (?100 °C, 1 min) followed by a transmetalation with CuBr?P(OEt)3 (?100 °C, 20 s). These ste

Tetra-substituted pyridinylimidazoles as dual inhibitors of p38α mitogen-activated protein kinase and c-jun N-terminal kinase 3 for potential treatment of neurodegenerative diseases

Tetra-substituted imidazoles were designed as dual inhibitors of c-Jun N-terminal kinase (JNK) 3 and p38α mitogen-activated protein (MAP) kinase. A library of 45 derivatives was prepared and evaluated in a kinase activity assay for their ability to inhibi

A convergent approach to (-)-callystatin a based on local symmetry

The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (-)-callystatin A was developed assembling three fragments through Julia-Kocienski olefination and Stille cross-coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme). Copyright

Synthesis and properties of seleno-analog MK-organic dye for photovoltaic cells prepared by CH functionalization reactions of selenophene derivatives

C-H arylation and homocoupling reactions of 2-formylselenophene were carried out with a palladium catalyst. By using these coupling reactions a seleno-analog of MK dye MK-49, which is an organic dye molecule of a dye-sensitized solar cell (DSSC), was synt

The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles

Rho-Rho-Rho your boat: A rhodium catalyst effects the regioselective oxidative coupling of enynes with N-aryl ureas (X=NR2) and N-vinylacetamides (X=C(O)Me), affording the corresponding 2-alkenylindoles and 2-alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3-aliphatic-substituted indole or pyrrole (see scheme).

Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P

A coordinatively unsaturated ruthenium complex catalyzed the formation of a carbon-carbon bond between two judiciously chosen alkene and alkyne partners in good yield, and in a chemo- and regioselective fashion, despite the significant degree of unsaturation of the substrates. The resulting 1,4-diene forms the backbone of the cytotoxic marine natural product amphidinolide P. The alkene partner was rapidly assembled from (R)-glycidyl tosylate, which served as a linchpin in a one-flask, sequential three-components coupling process using vinyllithium and a vinyl cyanocuprate. The synthesis of the alkyne partner made use of an unusual anti-selective addition under chelation-control conditions of an allyltin reagent derived from tiglic acid. In addition, a remarkably E-selective E2 process using the azodicarboxylate-triphenylphosphine system is featured. Also featured is the first example of the use of a β-lactone as a thermodynamic spring to effect macrolactonization. The oxetanone ring was thus used as a productive protecting group that increased the overall efficiency of this total synthesis. This work was also an opportunity to further probe the scope of the ruthenium-catalyzed alkene-alkyne coupling, in particular using enynes, and studies using various functionalized substrates are described.

Synthesis of 2E,4E,6E,11Z-octadecatetraenoic acid of the Rhizobium leguminosarum biovar viciae Nod factor

2E,4E,6E,11Z-Octadecatetraenoic acid was synthesized in a good yield and in a stereospecific manner by coupling a vinylborane compound and ethyl trans-3-iodoacrylate. The trienic system (E,E,E) was obtained by successive use of metal-catalyzed coupling and hydro-metallation reactions.

Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: A 1,1-difluoro-1-deoxy-d-xylulose

Readily available difluoroenol iodides and stannanes undergo palladium-catalysed coupling reactions with alkenylstannanes and iodides, respectively, to afford a trial set of difluorinated 1,3- and 1,4-dienes, which were then exposed to AD conditions. A nu