5459-35-8

Usage

Uses

Used in Organic Synthesis:
ETHYL 2-BROMOACRYLATE is used as a reagent in organic synthesis for its strong electrophilic nature, facilitating reactions such as the Michael addition and the Wittig reaction. Its ability to participate in these reactions is vital for the formation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, ETHYL 2-BROMOACRYLATE is used as an intermediate in the synthesis of various drugs. Its role in creating the molecular structures of pharmaceuticals is essential for the development of new medications.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, ETHYL 2-BROMOACRYLATE is utilized as an intermediate for the synthesis of different agrochemicals. Its contribution to the development of these chemicals is crucial for agricultural applications, such as pest control and crop protection.

InChI:InChI=1/C5H7BrO2/c1-3-8-5(7)4(2)6/h2-3H2,1H3

Upstream product

• 111-65-9 octane 
• 2678-54-8 ketene diethyl acetal 
• 75-65-0 tert-butyl alcohol 
• 74-95-3 1,1-dibromomethane 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 3674-13-3 2,3-dibromopropionic acid ethyl ester 
• 140-88-5 ethyl acrylate 
• 74-96-4 ethyl bromide 

Downstream Products

• 839-39-4 cyclopropane-1,1,2-tricarboxylic acid triethyl ester 
• 22286-82-4 2-phenyl-acrylic acid ethyl ester 
• 409359-85-9 2-(2-methylphenyl)propenoic acid ethyl ester 
• 128839-68-9 2-(4-methylphenyl)propenoic acid ethyl ester 
• 331779-03-4 ethyl 2-(4-bromophenyl)propenoate 
• 39729-00-5 2-(4-methoxyphenyl)propenoic acid ethyl eter 
• 409359-86-0 ethyl 2-(4-cyanophenyl)propenoate 
• 72800-63-6 ethyl ester of α-(p-nitrophenyl)acrylic acid 
• 75116-78-8 ethyl α-(3-benzoylphenyl)acrylate 
• 6448-12-0 ethyl 2-(4-isobutylphenyl)propenoate 
• 72800-64-7 ethyl 2-(4-fluorophenyl)acrylate 
• 34943-06-1 1-benzylaziridine-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

A SIMPLE SYNTHESIS OF 2-AZIDO-2-ALKENOATES

The title compounds are derived from 2,3-dibromoalkanoates by treatment with 3 equivalents of sodium azide.

Multigram-scale HPLC enantioseparation as a rescue pathway for circumventing racemization problem during enantioselective synthesis of ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Racemic ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate is a key synthon for the design of promising therapeutic drugs. It is mainly synthesized from racemic ethyl 2,3-dibromopropionate and 2-aminophenol in presence of K2CO3 in refluxed acetone. Unfortunately, synthesis of (R)- and (S)-enantiomers using the enantioselective version of this reaction, which should normally be performed with a double SN2 mechanism, is unsuitable due to a racemization process involving the dehydrobromination of enantiopure ethyl 2,3-dibromopropionate into ethyl 2-bromoacrylate. For the first time, the enantioselective version is studied (ee ≈ 55–66%), and the percentage of racemization process has estimated to around 34–46% after determination of the optimal experimental conditions for analytical HPLC enantioseparation of racemate. The influence of the experimental and purification conditions on the racemization rate is also studied. The results indicate that racemization occurs faster at the beginning of the reaction but the initiation of the double SN2 process takes place more faster to limit the racemization rate. The study of the influence of experimental conditions (reaction times, temperature, solvent or type of base, etc.) on the degree of racemization of the (R)- enantiomer is performed and shows that despite changes in the experimental conditions, the synthesis of the (R)- enantiomer is always accompanied by a racemization rate which is difficult in reducing. In parallel, (R)- and (S)-enantiomers are obtained in high enantiopurity (ee > 99.5%) by preparative HPLC enantioseparation of racemate on multigram scale and characterized by optical rotation measurements, ECD and UV spectra.

TRICYCLIC DEGRADERS OF IKAROS AND AIOLOS

Tricyclic cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway for therapeutic applications are described.

Convergent Route to β-Amino Acids and to β-Heteroarylethylamines: An Unexpected Vinylation Reaction

Various protected β2-amino acids can be prepared by radical addition of β-phthalimido-α-xanthyl propionic acid, both as the free acid or as the ethyl ester. Successive radical additions provide access to more complex structures. In the case of the free acid, addition to certain heteroaromatics leads directly to β-heteroarylethylamines through spontaneous decarboxylation of the intermediate adduct. Forcing the decarboxylation in some cases generated a vinyl group by decarboxylative elimination of the phthalimido group.

PHENYL AND PYRIDINYL SUBSTITUTED IMIDAZOLES AS MODULATORS OF RORyT

The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, Ra, Rb, Q1, and Q2 are defined in the specification. The invention also comprises a method of treating or ameliorating a ROR-γ-t mediated syndrome, disorder or disease, including wherein the syndrome, disorder or disease is selected from the group consisting of rheumatoid arthritis, psoriatic arthritis, and psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula I.

How Reaction Conditions May Influence the Regioselectivity in the Synthesis of 2,3-Dihydro-1,4-benzoxathiine Derivatives

The exploration of different reaction conditions aiming to obtain both 2,3-dihydro-1,4-benzoxathiine-2-yl derivatives and 2,3-dihydro-1,4-benzoxathiine-3-yl ones is reported. The treatment of 1,2-mercaptophenol with an organic base and a specific 2-bromo acrylate results in a solvent- and substrate-dependent exclusive solvation of O- and S-anions, thus managing the regioselectivity.

Competitive, substrate-dependent reductive debromination/dehydrobromination of 1,2-dibromides with triethylamine

The interaction of various 1,2-dibromides with NEt3 under various conditions (THF and DMF, respectively) at different temperatures was investigated. Our results from these reactions show that substrate dependent dehydrobrominations compete with reductive debrominations. A comprehensive discussion of these competitive pathways is offered.

Versatile magnetic resonance singlet tags compatible with biological conditions

The long lifetime of nuclear singlet states holds promise for the development of molecular tracers to study motional processes in proteins with increased precision or to act as imaging contrast agents. We introduce a singlet tag (STAG) based on bromoacrylate that is readily attached to a variety of biomolecules, compatible with biological conditions, and is relatively insensitive to the presence of molecular oxygen. The generality of this approach is demonstrated by tagging buildings blocks for biomolecules using a simple labelling route based on commercially available starting materials. Additionally, we demonstrate a singlet NMR experiment on the endogenous molecule phosphoenolpyruvate.

Robust eco-friendly protocol for the preparation of γ-hydroxy- α,β-acetylenic esters by sequential one-pot elimination-addition of 2-bromoacrylates to aldehydes promoted by LTMP in 2-MeTHF

An efficient and widely applicable preparation of γ-hydroxy-α, β-acetylenic esters is described by means of a one-pot dehydrobromination of a 2-bromoacrylate ester with LTMP followed by the electrophilic addition of the transient propiolate to different aldehydes in the eco-friendly solvent 2-MeTHF. The Royal Society of Chemistry 2012.

Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation

(Chemical Equation Presented) Dimethyl sulfoxide causes α/β-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing dehydrohalogenation procedures, this protocol is the most facile, practical, and environmentally benign process.