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3-Methoxythiophene

3-Methoxythiophene structure

CAS No:
17573-92-1
Formula:
C5H6OS
Chemical Name:
3-Methoxythiophene
Synonyms:
Thiophene,3-methoxy-;3-Methoxythiophene;Methyl 3-thienyl ether;3-Methoxythiofuran
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Clear light brown liquid

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.

3-Methoxythiophene Basic Attributes

Molecular Weight：

114.17

Exact Mass：

114.17

BRN：

106404

EC Number：

479-350-5

DSSTox ID：

DTXSID40170014

HScode：

2934999090

Characteristics

PSA：

37.5

XLogP3：

1.6

Appearance：

Clear light brown Liquid

Density：

1.143 g/mL at 25 °C(lit.)

Melting Point：

49-50 °C @ Solvent: Diethyl ether, Ligroine

Boiling Point：

80-82 °C @ Press: 65 Torr

Flash Point：

121 °F

Refractive Index：

n20/D 1.532(lit.)

Storage Conditions：

Flammables area

Vapor Pressure：

3.85mmHg at 25°C

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 1993 3/PG 3

wgk germany：

hazard class code：

safety instructions：

16-27-36/37/39

Precautionary statement(s)：

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501

Hazard Statements：

H226

RIDADR：

UN 1993

GHS Classification：

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory.|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory.

3-Methoxythiophene Use and Manufacturing

To a stirred solution of sodium methanolate (3.18g, 58.88mmol) in methanol (50mL) were added with N-methyl pyrrolidone (50mL) and 3-bromothiophene (8g, 49.07mmol). The mixture was heated to 110°C and then CuI (934mg, 4.91mmol) was added in one portion and kept reflux overnight. The reaction was cooled to room temperature and water (100mL) was added. The crude product was extracted with dichloromethane and the combined organic layers were washed with water and saturated aqueous NHGeneral procedure: A Teflon-lined autoclave (25 mL) was charged with MeONa (1.08 g, 20.0 mmol), MeOH (10 mL), CuCl (40 mg, 0.40 mmol), HCOOMe (0.25 mL, 0.97 g/mL, 4.0 mmol), and monohaloarene (10.0 mmol) then heated to 115 °C, with stirring, for 2 h. After completion of the reaction, the reactor was cooled to room temperature. The mixture was stirred for 0.5 h in the open, then concentrated to recover pure MeOH. Diethyl ether (15 mL) and dilute hydrochloric acid (1.6 M, 15 mL) were added to the residue. The mixture separated into two layers, and the aqueous phase was extracted with diethyl ether (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography on silica gel (mobile phase: petroleum ether–ethyl acetate 15:1) to furnish 1 (conversion and selectivity were determined by GC–MS analysis). The purity of the recovered MeOH was measured as more than 99 percent by GC, and the water content of the recovered MeOH was measured as less than 0.12 percent by use of the Karl Fischer method.Copper bromide (9.629 g, 67mmol) was weighed in a 500mL round bottom flask and placed in a nitrogen atmosphere glove box. Within the glove box sodium methoxide(54.067 g, 1000mmol) and dry NMP (171.476 g, 1729 mmol) were added, and the flask was stoppered and removed from the glove box. With a syringe, 3-bromothiophene (108.130 g, 663.2mmol) was added, and the solid reagents were allowed to dissolve at 110∘C for 15 min. After the addition of anhydrous methanol (100 mL), the reaction was allowed to reflux at 110

Computed Properties

Molecular Weight:114.17
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:114.01393598
Monoisotopic Mass:114.01393598
Topological Polar Surface Area:37.5
Heavy Atom Count:7
Complexity:56
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

114143-27-0

188290-36-0

114143-27-0

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