| Identification | More | [Name]
3-Methoxythiophene | [CAS]
17573-92-1 | [Synonyms]
3-METHOXYTHIOPHENE
METHYL 3-THIENYL ETHER
Methoxythiophene,95% | [EINECS(EC#)]
-0 | [Molecular Formula]
C5H6OS | [MDL Number]
MFCD00043894 | [Molecular Weight]
114.17 | [MOL File]
17573-92-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear light brown liquid | [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. ]
Flammables area | [form ]
Liquid | [color ]
Clear light brown | [Sensitive ]
Air Sensitive | [BRN ]
106404 | [InChI]
InChI=1S/C5H6OS/c1-6-5-2-3-7-4-5/h2-4H,1H3 | [InChIKey]
RFSKGCVUDQRZSD-UHFFFAOYSA-N | [SMILES]
C1SC=CC=1OC | [LogP]
1.810 (est) | [CAS DataBase Reference]
17573-92-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Thiophene, 3-methoxy-(17573-92-1) |
| Safety Data | Back Directory | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
13 | [REACH Registrations]
Inactive | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29339900 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Flam. Liq. 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear light brown liquid | [Uses]
3-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 Description]
3-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 Uses]
Thin polymer films were obtained from 3-methoxythiophene at the cathode in a dc discharge. | [Synthesis]
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 |
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