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2-Methoxythiophene

2-Methoxythiophene structure

CAS No:
16839-97-7
Formula:
C5H6OS
Chemical Name:
2-Methoxythiophene
Synonyms:
Thiophene,2-methoxy-;2-Methoxythiophene
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

CLEAR YELLOW LIQUID

2-Methoxythiophene Basic Attributes

Molecular Weight：

114.17

Exact Mass：

114.17

BRN：

106271

EC Number：

240-863-2

DSSTox ID：

DTXSID60168559

HScode：

29349990

Characteristics

PSA：

37.5

XLogP3：

1.9

Density：

1.120 g/cm³ @ Temp: 25 °C

Boiling Point：

74-75 °C @ Press: 50 Torr

Flash Point：

110 °F

Refractive Index：

n20/D 1.528(lit.)

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 1993 3/PG 3

wgk germany：

hazard class code：

safety instructions：

Precautionary statement(s)：

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

Hazard Statements：

H226

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 44 companies from 3 notifications to the ECHA C&L Inventory.

2-Methoxythiophene Use and Manufacturing

General 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.Step 1 To 3.5 mL anhydrous methanol under argon at 0 °C was added sodium metal (121 mg, 5.26 mmol). The resulting mixture was stirred vigorously until all the sodium metal was consumed, at which point the mixture was removed from the cooling bath. Copper(I) iodide (67 mg, 0.35 mmol) and 2-iodothiophene (736 mg, 3.50 mmol) were added and the resulting suspension heated to 70 °C and stirred vigorously for 6 h. After cooling to room temperature, 7 mL of 0.5 M aqueous potassium cyanide solution was added and the resulting mixture stirred for 15 minutes. Organics were extracted with ether (3 >< 1 mL), dried over magnesium sulfate, filtered and concentrated. The residue was subjected to chromatography on silica gel (100percent hexanes) to give 2-methoxythiophene (79 mg, 20percent). Used without further characterization. To a solution of 2-methoxythiophene (79 mg, 0.69 mmol) in 3.5 mL of 9: 1 tetrahydrofuran/hexamethylphosphoramide under argon at -78 °C was added H-butyllithium (0.30 mL, 2.5 M in hexanes) dropwise. After stirring at -78 °C for 20 minutes, dimethylformamide (0.27 mL, 3.5 mmol) was added in a single portion and the reaction mixture allowed to warm to room temperature while stirring, before being poured into 25 mL of 1 N hydrochloric acid. Organics were extracted with ether (2 χ 25 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (10-12percent ethyl acetate in hexanes) to give 5-methoxy-2-thiophenecarbaldehyde (71 mg, 72percent). Used without further characterization.

Computed Properties

Molecular Weight:114.17
XLogP3:1.9
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

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