62224-14-0

Basic information

• Product Name: ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE
• Synonyms: 2-Thiophenecarboxylic acid, 3-broMo-, ethyl ester;3-bromo-2-Thiophenecarboxylic acid ethyl ester;RARECHEM AL BI 0362;ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE
• CAS NO: 62224-14-0
• Molecular Formula: C₇H₇BrO₂S
• Molecular Weight: 235.1
• EINECS: 604-604-1
• Mol File: 62224-14-0.mol

Chemical Properties

• Boiling Point: 267.6°C at 760 mmHg
• Flash Point: 115.7°C
• Appearance: /
• Density: 1.572g/cm³
• Vapor Pressure: 0.00807mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE(62224-14-0)
• EPA Substance Registry System: ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE(62224-14-0)

Safety Data

• Hazardous Substances Data: 62224-14-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE is used as a synthetic intermediate for the development of various pharmaceuticals. Its unique bromine atom and thiophene structure facilitate the creation of complex organic molecules that can be utilized in the formulation of new drugs.
Used in Agricultural Industry:
In the agricultural sector, ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE is used as a precursor in the synthesis of agrochemicals. Its reactivity and structural properties enable the production of compounds that can be employed in the development of pesticides, herbicides, and other agricultural chemicals to improve crop yields and protect plants from pests.
Used in Chemical Research and Development:
ETHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE is utilized as a valuable tool in chemical research and development. Its distinctive properties and reactivity make it suitable for exploring new chemical reactions and synthesizing novel compounds with potential applications in various industries.

InChI:InChI=1/C7H7BrO2S/c1-2-10-7(9)6-5(8)3-4-11-6/h3-4H,2H2,1H3

Upstream product

• 872-31-1 3-Bromothiophene 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 3140-93-0 2,3-dibromothiophen 
• 623-49-4 ethyl cyanoformate 
• 1609-47-8 diethyl dicarbonate 
• 24287-92-1 2-Bromo-3-iodothiophene 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 7311-64-0 3-bromothiophene-2-carboxylic acid 
• 5751-83-7 ethyl 5-bromothiophene-2-carboxylate 
• 31823-64-0 methyl 3-amino-2-thiophenecarboxylate 

Downstream Products

• 70260-17-2 3-bromo-2-hydroxymethyl-thiophene 
• 23806-20-4 ethyl 3-phenyl-2-thiophenecarboxylate 

Relevant articles and documents

Magnesium Bisamide-Mediated Halogen Dance of Bromothiophenes

A magnesium bisamide-mediated halogen dance of bromothiophenes is described. The thienylmagnesium species generated in situ is more stable than the corresponding thienyllithium species, which was applied to trap the transient anion species with several electrophiles, such as allyl iodide, phenyl isocyanate, and tributylstannyl chloride. The utility of the magnesium bisamide-mediated halogen dance is useful in the concise synthesis of a medicinally advantageous compound via a one-pot, ester-directed halogen dance/Negishi cross coupling.

Potent Thiophene Antagonists of Human Complement C3a Receptor with Anti-Inflammatory Activity

Structure-activity relationships for a series of small-molecule thiophenes resulted in potent and selective antagonism of human Complement C3a receptor. The compounds are about 100-fold more potent than the most reported antagonist SB290157. A new compound JR14a was among the most potent of the new antagonists in vitro, assessed by (a) inhibition of intracellular calcium release (IC50 10 nM) induced in human monocyte-derived macrophages by 100 nM C3a, (b) inhibition of β-hexosaminidase secretion (IC50 8 nM) from human LAD2 mast cells degranulated by 100 nM C3a, and (c) selectivity for human C3aR over C5aR. JR14a was metabolically stable in rat plasma and in rat liver microsomes and efficacious in rats when given orally to suppress rat paw inflammation, macrophage and mast cell activation, and histopathology induced by intraplantar paw administration of a C3aR agonist. Potent C3aR antagonists are now available for interrogating C3a receptor activation and suppressing C3aR-mediated inflammation in mammalian physiology and disease.

Regiocontrolled Halogen Dance of Bromothiophenes and Bromofurans

The LDA (lithium diisopropylamide)-promoted regiocontrolled halogen dance of α-bromothiophenes and α-bromofurans is described. Bromothiophenes bearing a diethyl acetal moiety undergo selective deprotonation at the β-position adjacent to the bromo group. In contrast, oxazoline, ester, and amide groups act as directing groups in the initial lithiation step to generate a carbanion at the β-position neighboring the directing group to exclusively give the other regioisomer. These results can be applied to the regiocontrolled halogen dance of bromofuran derivatives.

Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters

The oxidative copper-catalyzed cross-coupling of functionalized alkyl boronic esters with primary amides is reported. Through the identification of appropriate diketimine ligands, conditions for efficient coupling of both primary and secondary alkyl boronic esters with diverse primary amides, including acetamide, have been developed.

Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles

A total of 19 alkylated heterocycles (thiophenes, benzothiophenes, pyrroles, furans) were prepared (36-99% yield) from the respective pyridin-2-yl-substituted precursors employing alkylboronic acids as the C-H alkylating reagents in an oxidative (Ag2

Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities

It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright

A simple and facile carboxylation method and its application for synthesis of liquid crystals

Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF 3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.

Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)3 as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.

Fused pyridine derivatives

The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.

ELECTROPHILIC TRICHLOROMETHYLATION OF SOME HALOGENATED THIOPHENES

The electrophilic trichloromethylation of 3-chloro-, 3-bromo-, and 3,4-dibromothiophene was studied. It is shown that reaction is directed towards position 2, accompanied by frequent formation of the corresponding substituted di-(2-thienyl)dichloromethane. Trichloromethylation of β-bromothiophenes is complicated by exchange of chlorine for bromine under the reaction conditions.