| Identification | More | [Name]
2-Methoxythiophene | [CAS]
16839-97-7 | [Synonyms]
2-METHOXYTHIOPHENE
METHYL 2-THIENYL ETHER
Thiophene, 2-methoxy- | [EINECS(EC#)]
240-863-2 | [Molecular Formula]
C5H6OS | [MDL Number]
MFCD00014526 | [Molecular Weight]
114.17 | [MOL File]
16839-97-7.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR YELLOW LIQUID | [Boiling point ]
151-152 °C/762 mmHg (lit.) | [density ]
1.133 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.528(lit.)
| [Fp ]
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 Data | Back Directory | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29349990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Flam. Liq. 3 |
| Hazard Information | Back Directory | [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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