2-Methoxythiophene Chemical Properties

Boiling point:

151-152 °C/762 mmHg (lit.)

Density 

1.133 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

110 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

BRN 

106271

InChI

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

InChIKey

OKEHURCMYKPVFW-UHFFFAOYSA-N

SMILES

C1(OC)SC=CC=1

LogP

2.130

CAS DataBase Reference

16839-97-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Methoxythiophene(16839-97-7)

Safety Information

Risk Statements 

10

Safety Statements 

16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methoxythiophene Usage And Synthesis

Chemical Properties

CLEAR YELLOW LIQUID

Uses

2-Methoxythiophene was used in thermal reaction (60°C) of (C₅Me₅)Rh(PMe₃)(Ph)H.

Synthesis Reference(s)

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

General Description

2-Methoxythiophene is a heterocyclic methyl enol ether and its reaction with o-quinone monoimide was studied. The intramolecular and intermolecular geometries of crystals of 2-methoxythiophene were investigated. Kinetics of the hydronium-ion catalysed hydrolysis of 2-methoxythiophene was reported.

Synthesis

Example 1 Preparation of 2-methoxythiophene: In a reactor, 300 g of 2-bromothiophene (1.84 mol), 2.64 g of copper(I) bromide (CuBr, 1 mol%), 18.4 g of polyethylene glycol dimethyl ether (PEG DME 500, 2 mol%), and 660 g of a methanolic solution of sodium methanolate (30% concentration, precursor concentration of 30.6%) were added in sequence. The mixture was heated to 90 °C for the reaction and the progress of the reaction was monitored by gas chromatography (GC) until the conversion was >98% (total reaction time 8h). Upon completion of the reaction, the reaction mixture was slowly poured into 500 g of water and filtered through Decalite. Subsequently, the aqueous phase was extracted twice with methyl tert-butyl ether (MTBE, 150 g each time). The organic phases were combined and purified by vacuum fractional distillation to give a final 182 g of 2-methoxythiophene (1.59 mol, 86.4% yield) with a GC purity of >99% (% area).

References

[1] Patent: US2008/71084, 2008, A1. Location in patent: Page/Page column 3-4
[2] Synthetic Communications, 1990, vol. 20, # 2, p. 213 - 216
[3] Tetrahedron, 1992, vol. 48, # 17, p. 3633 - 3652
[4] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8651 - 8664

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