16839-97-7

Basic information

• Product Name: 2-Methoxythiophene
• Synonyms: 2-METHOXYTHIOPHENE;METHYL 2-THIENYL ETHER;Thiophene, 2-methoxy-;2-Methoxythiophene,97%;Methoxythiophene;2-Methoxythiophene,99%;2-Methoxythiophene 97%
• CAS NO: 16839-97-7
• Molecular Formula: C₅H₆OS
• Molecular Weight: 114.17
• EINECS: 240-863-2
• Product Categories: Thiophenes;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiophene Series
• Mol File: 16839-97-7.mol

Chemical Properties

• Boiling Point: 151-152 °C762 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: Clear yellow liquid
• Density: 1.133 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 106271
• CAS DataBase Reference: 2-Methoxythiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxythiophene(16839-97-7)
• EPA Substance Registry System: 2-Methoxythiophene(16839-97-7)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 16839-97-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Methoxythiophene is used as a reactant in the thermal reaction (60°C) of (C5Me5)Rh(PMe3)(Ph)H. This application takes advantage of its chemical properties to facilitate the synthesis of various compounds.
Used in Pharmaceutical Research:
2-Methoxythiophene is used as a research compound for studying its potential applications in the pharmaceutical industry. Its chemical properties and reactivity make it a candidate for the development of new drugs and therapeutic agents.
Used in Material Science:
The investigation of the intramolecular and intermolecular geometries of 2-methoxythiophene crystals can contribute to the field of material science, particularly in understanding the structural properties and potential applications of such compounds in various materials.
Used in Chemical Kinetics Studies:
The reported kinetics of the hydronium-ion catalysed hydrolysis of 2-methoxythiophene can be utilized in academic and industrial research to understand the reaction mechanisms and rates, which can be beneficial for optimizing chemical processes and developing new catalysts.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 3697, 1953 DOI: 10.1021/ja01111a027

InChI:InChI=1/C5H6OS/c1-6-5-3-2-4-7-5/h2-4H,1H3

Upstream product

• 1003-09-4 2-bromothiophene 
• 124-41-4 sodium methylate 
• 3437-95-4 2-Iodothiophene 
• 67-56-1 methanol 
• 3354-32-3 2,5-dihydro-2H-2-oxothiophene 
• 77998-60-8 (5-Methoxy-thiophen-2-yl)-trimethyl-silane 
• 78395-08-1 4-Iodo-2-methoxythiophene 
• 3140-93-0 2,3-dibromothiophen 
• 19259-06-4 diiodo-2,4 thiophene 

Downstream Products

• 163928-54-9 5-methoxy-2,2’-bithiophene 
• 492-97-7 2,2'-Bithiophene 
• 144852-97-1 3,3'-dimethoxy-2,2'-bithiophene 
• 77133-30-3 2-methoxy-3,5-dibromothiophene 
• 111359-25-2 α-(4-methoxy phenyl)-α-hydroxy-N,N dimethylthioacetamide 
• 527-17-3 Duroquinone 
• 882-33-7 diphenyldisulfane 
• 32136-52-0 dimethyl 3-methoxyphthalate 
• 140646-38-4 5-methoxy-2-thiophenesulfonamide 
• 596819-12-4 2-(5-methoxythiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 251999-87-8 (E)-p-nitrophenyl 3-(5-methoxy-2-thienyl)acrylate 

Relevant articles and documents

A ligand-free, powerful, and practical method for methoxylation of unactivated aryl bromides by use of the CuCl/HCOOMe/MeONa/MeOH system

A ligand-free, powerful, and practical method for mono and polymethoxylation of unactivated aryl bromides has been developed; CuCl was used as catalyst, HCOOMe as cocatalyst, and methanolic MeONa as both nucleophile and solvent. This eco-friendly procedure is characterized by operational simplicity, inexpensive substrates (unactivated mono to polybromoarenes), full conversion, and direct recovery of pure MeOH.

ANTIBACTERIAL AGENTS: ARYL MYXOPYRONIN DERIVATIVES

The invention provides compounds of formula la, lb and Ic: [Formula Ia, Ib, and Ic] and salts thereof, wherein variables are as described in the specification, as well as compositions comprising a compound of formula Ia-Ic, methods of making such compounds, and methods of using such compounds, e.g., as inhibitors of bacterial RNA polymerase and as antibacterial agents.

Facile preparation of thiophene C2-ethers using the Mitsunobu reaction

The preparation of thiophene ethers generally requires forcing conditions thus limiting the choice of alkyl substituent. Herein, we report the first successful generally applicable conditions for the selective O-alkylation of 2(5H)-thiophenone.

Method for preparing alkyl ethers and aryl ethers

Method for preparing compounds of the formula (III) by reacting compounds of the formula (II) with a) an alcoholate or b) an alcohol R1-OH and a base in the presence of a Cu-containing catalyst and of a ligand, where X1-5 are independently of one another either carbon or nitrogen, or in each case two adjacent X1R1, with i=1?6, linked by a formal double bond together O, S, NRH or Nrl. The ligands preferably employed are acyclic and/or cyclic oligo- and polyglycols, oligo- and polyamides or oligo- and polyamine glycols of the general formula (IV) k is an integer >0 and n is an integer >1; X and Y are independently of one another O, NH or NR1.

2-(substituted-phenyl)amino-imidazoline derivatives

This invention relates to IP receptor antagonists selected from the group of compounds represented by Formula I: where:R1 is a group represented by formula (A), (B) or (C); and other substituents as defined in the specification, and their pharmaceutically acceptable salts or crystal forms thereof; and pharmaceutical compositions containing them; and methods for their use as therapeutic agents.

Synthesis and antitumor activity of duocarmycin derivatives: A-ring pyrrole compounds bearing 5-membered heteroarylacryloyl groups

A series of A-ring pyrrole compounds of duocarmycin bearing 5-membered heteroarylacryloyl groups (thienylacryloyl and pyrrolylacryloyl) and heteroarylcarbonyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the thienylacrylates displayed in vitro anticellular activity equivalent to 4'-methoxycinnamates. Among the 8- O-[(N-methylpiperazinyl)carbonyl] derivatives of methoxy-thienylacrylates, compound 11b, having 4'-methoxy-2'-thienylacryloyl as segment-B (Seg-B), showed remarkably potent antitumor activity and low peripheral blood toxicity in vivo, which were equal to those of 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates, compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in SegB. On the other hand, the 2'-pyrrolylacrylates having a double bond as spacer showed 102- to 103- fold stronger anticellular activity than 2'-pyrrolecarboxylates (IC500.3 nM, 72 h-exposure). The 8-O-acetate and 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 2'-pyrrolylacrylates exhibited an antitumor effect at a lower dose compared with the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'- methoxycinnamate (1j). Moreover, it was expected that the antitumor activity would be increased by the strength of the extra hydrogen bond formed between the nitrogen of the pyrrole amido group and DNA, owing to the increase of the number of N-methyl-2'-pyrrolecarboxamide units. However, 2'-pyrrolylacrylates having three N-methyl-2'-pyrrolecarboxamide units showed nearly equal antitumor activity to 2'-pyrrolylacrylates having only one N-methyl-2'- pyrrolecarboxamide unit.

Copper(I) Halide Catalysed Synthesis of Alkyl Aryl and Alkyl Heteroaryl Ethers

A number of alkyl aryl and alkyl heteroaryl ethers have been prepared from (hetero) aryl halides (mainly bromides) and sodium alkoxides, using copper(I)bromide as a catalyst.The influence of the main solvent, the halogen atom, reaction temperature and the presence of oxygen upon the rate and selectivity has been studied.Furthermore the decomposition of the catalyst and the reduction of the aryl halide are studied.

SYNTHESIS AND TRANSFORMATIONS OF SULFIDES OF THE THIOPHENE SERIES.

Isomeric alkoxy(alkylthio)formylthiophenes were synthesized from 4-iodo-2-methoxythiophene, and the structures of the products of Vilsmeier formylation of 2-methoxy-5-methythiothiophene were confirmed.

PROTIODESILYLATION OF SUBSTITUTED 2-TRIMETHYLSILYLTHIOPHENS

First-order rate constats at 50 deg C have been determined for cleavage of the thiophen compounds XC4H2SSiMe3-2 in mixtures of (a) MeOH (5 vol.) with aqueous HClO4 (2 vol.) and (b) CH3CO2H (4 vol.) with aqueous H2SO4 (3 vol.) Relative rates krel, in the first medium are (X =) 5-OMe, 7 200; 5-Me, 36; H, 1.00; 5-Cl, 1.08E-1; 5-Br, 9.0E-2; 3-Br, 5.0E-2; 4-Br, 4.9E-3, and in the second medium 5-Me, 36; H, 1.00; 5-Cl, 1.28E-1; 5-Br, 9.8E-2; 3-Br, 5.5E-2; 4-Br, 6.5E-3; 5-NO2, 9.1E-7; 3-NO2, 7.1E-7.Except for the nitro-compounds, the two sets of log krel values show excellent linear correlations with values for the corresponding XC6H4SiMe3 compounds, with 3-, 4-, and 5-X in the thiophen ring being taken as equivalent to o-, m-, and p-X groups, respectively, in the benzene ring, the effects of substituents being a litle larger in the thiophen than the benzene system; 3- and 5-O2NC4H2SSiMe3 are less reactive than would be expected from the correlations.Again with the exception of the data for the nitro-compound, the krel values for the 4- and 5- substituted thiophens show very good correlation with ?m+ and ?p+ constants.