1609-92-3

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-3-BROMOACRYLIC ACID is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its reactivity and structural properties to facilitate the development of new drugs and improve existing ones.
Used in Agrochemical Industry:
(Z)-3-BROMOACRYLIC ACID is utilized as a building block in the production of agrochemicals, contributing to the formulation of effective and targeted pest control solutions.
Used in Specialty Chemicals Production:
(Z)-3-BROMOACRYLIC ACID is employed as a versatile component in the synthesis of specialty chemicals, which are tailored for specific applications in various industries.
Used as a Reagent in Organic Synthesis:
(Z)-3-BROMOACRYLIC ACID is used as a reagent in the synthesis of a range of compounds, including peptides, due to its ability to participate in various chemical reactions and contribute to the formation of desired products.
Used in Polymer Preparation:
(Z)-3-BROMOACRYLIC ACID is used as a precursor in the preparation of polymers, where its unique properties can influence the characteristics of the resulting polymeric materials.
Used in Material Development:
(Z)-3-BROMOACRYLIC ACID is studied for its potential use in the development of new materials, indicating its role in advancing material science and technology.
Used in Pharmaceutical Research:
(Z)-3-BROMOACRYLIC ACID is a valuable chemical in pharmaceutical research, where it is explored for its potential to contribute to the discovery and understanding of novel therapeutic agents and mechanisms.

InChI:InChI=1/C3H3BrO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-

Upstream product

• 3475-39-6 1,1,3-tribromoacetone 
• 5469-80-7 3,3-dibromo-propionic acid 
• 471-25-0 Propiolic acid 

Downstream Products

• 6213-89-4 (E)-3-bromoacrylic acid 
• 6214-22-8 methyl (Z)-3-bromoacrylate 
• 35304-86-0 (Z)-5-phenyl-2,4-pentadien-4-olide 
• 78877-46-0 diethyl 3-methyl-6-oxo-2H,6H-pyrido<2,1-b><1,3>thiazine-4,9-dicarboxylate 
• 139306-23-3 4-(4-ethoxycarbonyl-2,3-dihydro-5-methyl-6H-1,3-thiazin-2-ylidene)glutaconic acid anhydride 
• 139306-24-4 ethyl 2-(N,N'-dicyclohexyl-1-ethoxycarbonyl-4,6-dioxo-5,7-diazahept-2E-enylidene)-2,3-dihydro-5-methyl-6H,1,3-thiazine-4-carboxylate 
• 186806-47-3 5-[(2S,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-prop-(Z)-ylidene]-5H-furan-2-one 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 425642-79-1 5-phenyl-2,4-pentadiynyl (Z)-3-bromo-2-propenoate 
• 444890-79-3 (Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester 
• 444890-80-6 (Z)-5-[2-((Z)-3-Bromo-acryloyloxy)-phenyl]-pent-2-en-4-ynoic acid methyl ester 
• 444890-81-7 (Z)-3-bromopropenoic acid 2-iodophenyl ester 

Relevant academic research and scientific papers

A Novel Stereospecific Hydrohalogenation Reaction of Propiolates and Propiolic Acid

(Z)-3-Halo-propenoates or -propenoic acids have been synthesized stereospecifically by the reaction of lithium halides in acetic acid with propiolates or propiolic acid, respectively.

QUINAZOLINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF

Disclosed are a quinazoline derivative, a preparation method therefor, and a pharmaceutical composition and an application thereof. The present invention provides a compound represented by general formula I, a stereoisomer thereof and a pharmaceutical acceptable salt or a solvate thereof. The quinazoline derivative of the present invention has a unique chemical structure, is characterized by irreversibly inhibiting EGFR tyrosine kinase, has high biological activity, apparently improves the inhibiting effect on the EGFR tyrosine kinase, has quite strong tumor inhibiting effect on tumor cells and a transplantation tumor pathological model of animal tumors, and has good market developing prospects.

POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

Highly efficient and selective procedures for the synthesis of γ-alkylidenebutenolides via palladium-catalyzed ene-yne coupling and palladium- or silver-catalyzed lactonization of (Z)-2-en-4-ynoic acids. Synthesis of rubrolides A, C, D, and E

The diacetates of rubrolides A, C, D, and E (1 a-d) were prepared in modest yields by the Pd-catalyzed cross coupling-lactonization tandem reaction of 5a or 5b with 6a or 6b using Cl2Pd(PPh3)2 and CuI as catalysts. The feasibility of converting the diacetates into rubrolides was demonstrated by the synthesis of rubrolide C by treatment of 1b with methanolic K2CO3 in THF. A detailed investigation of various parameters and conditions has indicated that formation of the corresponding six-membered lactones 7 and/or the cross coupling-lactonization-Heck substitution products 11 can be serious side reactions under non-optimized conditions and that the use of Pd(PPh3)4 rather than phosphine-free complexes, e.g., CI2Pd(PhCN)2, or complexes of low phosphine content, e.g., Cl2Pd(PPh3)2, along with CuI and NEt3 in MeCN provides satisfactory conditions for the cross coupling-lactonization tandem reaction. Thus, the diacetate of rubrolide A (1a) was prepared in 70% isolated yield. The optimized conditions reported herein appear to be generally applicable to the stereoselective and regioselective synthesis of γ-alkylidenebutenolides in a highly efficient manner.

Vicinal C-H Coupling as an Acid to Stereochemical Substituted Propenoic Acid

Two isomeric pairs of 3-bromopropenoic acids were prepared and vicinal C-H couplings were measured in their 13C n.m.r. spectra.Complete C-H coupling schemes were also obtained for these and several other propenoic acids.It was seen that the ranges for 3Jtrans and 3Jcis did not overlap, and so a stereochemical assignment based upon n.m.r. data for a single isomer can be made with confidence.

A Novel Regio- and Stereospecific Hydrohalogenation Reaction of 2-Propynoic Acid and Its Derivatives

2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products.A rationale for the regio- and stereospecifity is briefly discussed.

The synthesis of (6R)-[6-2H]- And (6S)-[6-2H]5-enolpyruvylshikimate-3-phosphate

(6R)-[6-2H]- and (6S)-[6-2H]-enolpyruvylshikimate-3-phosphate have been synthesised for the kinetic analysis of the chorismate synthase reaction. The synthesis uses purified shikimate kinase and EPSP synthase for enantiospecific biotransformations and also clarifies the stereochemical course of the Diels-Alder reaction in the synthesis of shikimic acid.

1-VINYL-4-METHYL-2,6,7-TRIOXABICYCLOOCTANES: UNSATURATED HOMOENOLATE ANION EQUIVALENTS

The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclooctane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkylhalides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.

Palladium-Catalyzed Triethylammonium Formate Reductions. 4. Reduction of Acetylenes to Cis Monoenes and Hydrogenolysis of Tertiary Allylic Amines

Eight phenyl-conjugated and double bond conjugated acetylenes were reduced with triethylammonium formate and a palladium on carbon catalyst.Cis olefins were obtained in good yields in five examples. 4-Nitrodiphenylacetylene gave only 4-aminodibenzyl and (Z)-methyl non-2-en-4-ynoate gave mainly the E,Z dienoate. 1-Phenyl-3-methylbut-3-en-1-yne gave the cis diene initially, but it isomerized partially under the reaction conditions.Five tertiary allylic amines were shown to undergo hydrogenolysis with the same reducing agent and catalyst to give mixtures of two isomeric olefins in moderate to good yields.

Stereospecific Alkylation of the Schiff Base Ester of Alanine with 2-Substituted-(E)- and -(Z)-vinyl Bromides. An Efficient Synthesis of 2-Methyl-(E)-3,4-didehydroglutamic Acid, a Potent Substrate-Induced Irreversible Inhibitor of L-Glutamate-1-decarboxylase.

The nucleophilic vinylic substitution by the enolate of methyl N-benzylidenealanate (1) of (E)- and (Z)-vinylbromides 4 and 5 has been examined as an approach to the synthesis of the E and Z isomers of 2-methyl-3,4-didehydroglutamic acid.Under aprotic conditions, the nucleophilic displacement has been found to proceed stereospecifically with retention of configuration of the double bond to afford in good yield the corresponding (E)- and (Z)-substituted products.The configuration of the substitution products has been assigned from the analysis of their 1H NMR spectra on the basis of the value of the coupling constant of the vicinal vinyl ic protons.Subsequent removal of the protecting groups from the substitution products 6 in the E series gives the corresponding 2-methyl-(E)-3,4-didehydroglutamic acid derivatives 2 in good yield.The Z isomers 3 prove to be very unstable and have not been isolated.