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.)

Flash point:

121 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

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 Information

Risk Statements 

10

Safety Statements 

16-27-36/37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

13

HazardClass 

3

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:3-Methoxythiophene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Methoxythiophene Usage And Synthesis

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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