95201-93-7

Basic information

• Product Name: METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE;4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;4-Bromo-3-hydroxy-2-(methoxycarbonyl)thiophene
• CAS NO: 95201-93-7
• Molecular Formula: C₆H₅BrO₃S
• Molecular Weight: 237.07
• Product Categories: Esters;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes
• Mol File: 95201-93-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 79-80°C
• Boiling Point: 247.9±35.0℃ (760 Torr)
• Flash Point: 103.7±25.9℃
• Appearance: /
• Density: 1.803±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.016mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.93±0.15(Predicted)
• Water Solubility: Sparingly Soluble in water 0.95 g/L @ 25°C.
• CAS DataBase Reference: METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE(95201-93-7)
• EPA Substance Registry System: METHYL 4-BROMO-3-HYDROXYTHIOPHENE-2-CARBOXYLATE(95201-93-7)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 95201-93-7(Hazardous Substances Data)

Usage

Uses

The synthesis of the thienopyranone scaffold began with the alkylation of methyl 4-bromo-3-hydroxythiophene-2-carboxylate with N-acetylmorpholine.

InChI:InChI=1/C6H5BrO3S/c1-10-6(9)5-4(8)3(7)2-11-5/h2,8H,1H3

Upstream product

• 5118-06-9 methyl 3-hydroxy-2-thiophenecarboxylate 
• 95201-94-8 methyl 2-chloro-3-oxo-2,3-dihydrothiophen-2-yl-carboxylate 

Downstream Products

• 110545-67-0 methyl 4-bromo-3-methoxythiophene-2-carboxylate 
• 943324-15-0 methyl 4-bromo-3-(4-methylphenyl)-2-thiophenecarboxylate 
• 1346685-14-0 C₂₀H₁₈O₂S 
• 1346684-98-7 methyl 4-(4-methylphenyl)-3-([(trifluoromethyl)sulfonyl]oxy)-2-thiophenecarboxylate 
• 1346684-99-8 methyl 4-bromo-3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-thiophenecarboxylate 
• 1346685-00-4 methyl 4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-([(trifluoromethyl)sulfonyl]oxy)-2-thiophenecarboxylate 
• 1346685-06-0 (4-bromo-3-[4-(methyloxy)phenyl]-2-thienyl)methanol 
• 1346685-07-1 2-(hydroxymethyl)-4-[4-(methyloxy)phenyl]-3-thienyl trifluoromethanesulfonate 
• 1609650-69-2 C₁₄H₁₀O₃S 
• 1263795-44-3 8-(2-fluorophenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine hydrochloride 
• 1263795-42-1 8-(3-fluorophenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine hydrochloride 
• 1263795-25-0 8-(3-methoxyphenyl)-2-methyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine hydrochloride 
• 1263795-07-8 8-(3-fluorophenyl)-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine hydrochloride 
• 1263795-45-4 tert-butyl 8-(2-fluorophenyl)-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate 

Relevant articles and documents

Reactions with 3-hydroxy-2-methoxycarbonylthiophene; I. Synthesis of 3-thienyloxyacetic acid and its (Nuclear) chloro and bromo derivatives

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New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase

Deoxyhypusine synthase (DHPS) is the primary enzyme responsible for the hypusine modification and, thereby, activation of the eukaryotic translation initiation factor 5A (eIF5A), which is key in regulating the protein translation processes associated with tumor proliferation. Although DHPS inhibitors could be a promising therapeutic option for treating cancer, only a few studies reported druglike compounds with this inhibition property. Thus, in this work, we designed and synthesized a new chemical series possessing fused ring scaffolds designed from high-throughput screening hit compounds, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative (26d) with potent inhibitory activity; furthermore, the X-ray crystallographic analysis of the DHPS complex with 26d demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional analysis of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

Regioselective and efficient halogenation of 4,5-unsubstituted alkyl 3-hydroxypyrrole/3-hydroxythiophene-2-yl-carboxylates

Substituted heterocycles, such as pyrrole and thiophene, are commonly found in the field of pharmaceutical and material sciences. Here we studied the reactivity of 4,5-unsubstituted alkyl 3-hydroxypyrrol-2-yl-carboxylates and 4,5-unsubstituted alkyl 3-hydroxythiophen-2-yl-carboxylates in different halogenation conditions, due to their interest as building blocks in the synthesis of bioactive compounds and materials. We describe herein the regioselective monohalogenation of 3-hydroxypyrroles and 3-hydroxythiophenes in mild conditions with common halogenation agents. The selectivity of the halogenation was studied. Optimized one-step reaction conditions were found for monobromination and monochlorination. Finally, we observed that bromination with N-bromosuccinimide (NBS) took place at the C4 position of the heterocycle, while chlorination with SO2Cl2 led to C5-halogenated derivatives.