108499-32-7

Basic information

• Product Name: Methyl 5-(bromomethyl)-2-thiophenecarboxylate
• Synonyms: Methyl 5-(bromomethyl)-2-thiophenecarboxylate;5-(bromomethyl)-2-thiophenecarboxylate;2-Thiophenecarboxylic acid, 5-(bromomethyl)-, methyl ester
• CAS NO: 108499-32-7
• Molecular Formula: C₇H₇BrO₂S
• Molecular Weight: 235.09828
• Mol File: 108499-32-7.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: Methyl 5-(bromomethyl)-2-thiophenecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-(bromomethyl)-2-thiophenecarboxylate(108499-32-7)
• EPA Substance Registry System: Methyl 5-(bromomethyl)-2-thiophenecarboxylate(108499-32-7)

Safety Data

• Hazardous Substances Data: 108499-32-7(Hazardous Substances Data)

Usage

General Description

Methyl 5-(bromomethyl)-2-thiophenecarboxylate, also known as Methyl bromomethyl-2-thiophene-5-carboxylate, is a compound with the molecular formula C9H9BrO2S. It is a member of the carboxylate esters chemical class and is commonly used in the field of pharmaceutical and organic synthesis. This chemical is often utilized in the development and production of various drugs and pharmaceutical products. It is also known for its potential as an intermediate in the manufacturing of agrochemicals and other specialty chemicals. Methyl 5-(bromomethyl)-2-thiophenecarboxylate plays a crucial role in the synthesis of various pharmaceutical and agrochemical compounds, making it valuable in the chemical industry.

Upstream product

• 956117-83-2 5-(t-butyldimethyl-silanyloxymethyl)thiophene-2-carboxylic acid 
• 956117-84-3 5-(t-butyldimethyl-silanyloxymethyl)-thiophene-2-carboxylic acid methyl ester 
• 19432-69-0 methyl 5-methylthiophene-2-carboxylate 
• 530145-16-5 5-hydroxymethyl-2-thiophenecarboxylic acid methyl ester 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 

Downstream Products

• 1311291-25-4 5-(4-amidino-2-fluorophenoxycarbonyl)thiophen-2-ylacetic acid trifluoroacetic acid salt 
• 61855-04-7 5-methoxymethyl-thiophene-2-carboxylic acid 

Relevant articles and documents

Harnessing the Role of HDAC6 in Idiopathic Pulmonary Fibrosis: Design, Synthesis, Structural Analysis, and Biological Evaluation of Potent Inhibitors

Idiopathic pulmonary fibrosis (IPF) is an interstitial lung disease characterized by a progressive-fibrosing phenotype. IPF has been associated with aberrant HDAC activities confirmed by our immunohistochemistry studies on HDAC6 overexpression in IPF lung tissues. We herein developed a series of novelhHDAC6 inhibitors, having low inhibitory potency overhHDAC1 andhHDAC8, as potential pharmacological tools for IPF treatment. Their inhibitory potency was combined with lowin vitroandin vivotoxicity. Structural analysis of 6h and structure-activity relationship studies contributed to the optimization of the binding mode of the new molecules. The best-performing analogues were tested for their efficacy in inhibiting fibrotic sphere formation and cell viability, proving their capability in reverting the IPF phenotype. The efficacy of analogue 6h was also determined in a validated human lung model of TGF-β1-dependent fibrogenesis. The results highlighted in this manuscript may pave the way for the identification of first-in-class molecules for the treatment of IPF.

Base promotedgem-difluoroolefination of alkyl triflones

A new synthesis ofgem-difluoroalkenes from readily available alkyl triflones and difluorocarbene precursors such as TMSCF2Br has been reported. The reaction, regardless of electronic effect, givesgem-difluoroalkenes in good to excellent yields. The mechanism may involve deprotonation of triflones, nucleophilic addition, and the elimination of SO2CF3

Development of a practical and scalable route for the preparation of the deacetoxytubuvaline (dTuv) fragment of pretubulysin and analogs

We present herein a novel and convenient route for the scaling-up of the dTuv fragment of pretubulysin. The newly conceived chemical path involves a practical and efficient one-step procedure for the preparation of a key thiazole intermediate, followed by high-yielding Wittig olefination/reduction steps. The optimized route, starting from the inexpensive and non-toxic l-cysteine, encompasses five synthetic steps and only two chromatographic purifications, thus displaying a dramatically increased overall yield. The versatility of the proposed approach also provides new hints for the exploration of pretubulysin derivatives bearing diverse heterocyclic portions.