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2-Methoxythiophene

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CAS:16839-97-7
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2-Methoxythiophene Basic information
Product Name:2-Methoxythiophene
Synonyms:Methoxythiophene;2-METHOXYTHIOPHENE;METHYL 2-THIENYL ETHER;Thiophene, 2-methoxy-;2-Methoxythiophene,97%;2-Methoxythiophene,99%;2-Methoxythiophene 97%;2-Methoxythiophene>
CAS:16839-97-7
MF:C5H6OS
MW:114.17
EINECS:240-863-2
Product Categories:Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Thiophene Series
Mol File:16839-97-7.mol
2-Methoxythiophene Structure
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.)
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
InChIInChI=1S/C5H6OS/c1-6-5-3-2-4-7-5/h2-4H,1H3
InChIKeyOKEHURCMYKPVFW-UHFFFAOYSA-N
SMILESC1(OC)SC=CC=1
LogP2.130
CAS DataBase Reference16839-97-7(CAS DataBase Reference)
NIST Chemistry Reference2-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 Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2-Methoxythiophene Usage And Synthesis
Chemical PropertiesCLEAR YELLOW LIQUID
Uses2-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 Description2-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
2-Bromothiophene

1003-09-4

Sodium Methoxide

124-41-4

2-Methoxythiophene

16839-97-7

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
2-Methoxythiophene Preparation Products And Raw materials
Raw materials2-Bromothiophene-->2-Iodothiophene-->Methanol-->Sodium Methoxide
Preparation Products3-IODOTHIOPHENE
Tag:2-Methoxythiophene(16839-97-7) Related Product Information
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