3-Methoxythiophene CAS 17573-92-1

Introduction:Basic information about 3-Methoxythiophene CAS 17573-92-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

3-Methoxythiophene Basic information

Product Name:3-Methoxythiophene
Synonyms:3-Methoxythiophene,98%;m-Methoxythiophene;3-Methoxythiophene, 98% 5GR;3-Methoxythiophene,99%;3-METHOXYTHIOPHENE;METHYL 3-THIENYL ETHER;Methoxythiophene,95%;3-Methoxythiophene>
CAS:17573-92-1
MF:C5H6OS
MW:114.17
EINECS:000-000-0
Product Categories:Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Sulphur Derivatives;Thiophene&Benzothiophene;Thiophens;Thiophene Series;Pyridines ,Halogenated Heterocycles
Mol File:17573-92-1.mol

3-Methoxythiophene Chemical Properties

Melting point 49-50 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
Boiling point 80-82 °C/65 mmHg (lit.)
density 1.143 g/mL at 25 °C (lit.)
refractive index n20/D 1.532(lit.)
Fp 121 °F
storage temp. Keep in dark place,Inert atmosphere,2-8°C
form Liquid
color Clear light brown
Sensitive Air Sensitive
BRN 106404
InChIInChI=1S/C5H6OS/c1-6-5-2-3-7-4-5/h2-4H,1H3
InChIKeyRFSKGCVUDQRZSD-UHFFFAOYSA-N
SMILESC1SC=CC=1OC
LogP1.810 (est)
CAS DataBase Reference17573-92-1(CAS DataBase Reference)
NIST Chemistry ReferenceThiophene, 3-methoxy-(17573-92-1)

Safety Information

Risk Statements 10
Safety Statements 16-27-36/37/39
RIDADR UN 1993 3/PG 3
WGK Germany 3
13
HazardClass 3
PackingGroup III
HS Code 29339900
Storage Class3 - Flammable liquids
Hazard ClassificationsFlam. Liq. 3

3-Methoxythiophene Usage And Synthesis

Chemical PropertiesClear light brown liquid
Uses3-Methoxythiophene, is a heterocyclic building block used for the synthesis of more complex compounds containing Thiophene moiety. It can also be used for the preparation of novel thiophenyl-methylene-9H-fluorene-based low bandgap polymers.
Synthesis Reference(s)Synthetic Communications, 20, p. 213, 1990 DOI: 10.1080/00397919008052285
General Description3-Methoxythiophene is a thiophene. The intramolecular and intermolecular geometries of crystals of 3-methoxythiophene were studied. Spectroscopic studies of bipolarons derived from oligomerized 3-methoxythiophene in solution has been reported. The electropolymerization of 3-methoxythiophene on Pt and Fe electrodes in an aqueous micellar medium containing sodium dodecyl sulfate and 10-3M bithiophene has been reported. Thin polymer films of 3-methoxythiophene at the cathode in a direct current discharge have been prepared.
Materials UsesThin polymer films were obtained from 3-methoxythiophene at the cathode in a dc discharge.
Synthesis

872-31-1

124-41-4

17573-92-1

Example 2 Preparation of 3-methoxythiophene: 185 g of 3-bromothiophene (1.13 mol), 3.24 g of copper(I) bromide (CuBr, 2 mol%) and 14.1 g of PEG DME 250 (5 mol%) were added to the reactor. Subsequently, sodium methanol solution (30% concentration, precursor concentration 30.4) was added and the mixture was heated to 90 °C. The conversion was monitored by GC during the reaction and was >98% (reaction time totaled 10 hours). Upon completion of the reaction, the mixture was poured into 300 g of water. After filtration through decalite, the mixture was extracted twice with 120 g of methyl tertiary butyl ether (MTBE). The organic phases were combined and subjected to vacuum fractionation to afford 117.4 g of 3-methoxythiophene (1.03 mol, 91% yield) with a GC purity of >99% (% area).

References[1] Patent: US2008/71084, 2008, A1. Location in patent: Page/Page column 4
[2] Polymer, 2013, vol. 54, # 18, p. 4930 - 4939
[3] Journal of Materials Chemistry C, 2015, vol. 3, # 7, p. 1595 - 1603
[4] Chemical Communications, 2013, vol. 49, # 49, p. 5538 - 5540
[5] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8651 - 8664

3-Methoxythiophene Preparation Products And Raw materials

Raw materials3-Bromothiophene-->Methanol-->Sodium Methoxide
Preparation Products2-iodo-3-Methoxythiophene-->3-Methoxythiophene-2-boronic acid pinacol ester-->1-(3-Methoxythien-2-yl)ethanone
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