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| CAS No.: | 288-05-1 | ||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Name: | Selenophene | ||||||||||||||
| Article Data: | 39 | ||||||||||||||
| Cas Database | |||||||||||||||
| Molecular Structure: | |||||||||||||||
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| Formula: | C4H4 Se | ||||||||||||||
| Molecular Weight: | 131.036 | ||||||||||||||
| Synonyms: | Selenacyclopentadiene;Selenofuran | ||||||||||||||
| EINECS: | N/A | ||||||||||||||
| Density: | g/cm3 | ||||||||||||||
| Melting Point: |
−30 °C(lit.) |
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| Boiling Point: |
110-111 °C(lit.) |
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| Flash Point: | 20.6°C | ||||||||||||||
| Solubility: | N/A | ||||||||||||||
| Appearance: | N/A | ||||||||||||||
| Hazard Symbols: |
 
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| Risk Codes: | 23/25-33-50/53 | ||||||||||||||
| Safety: |
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| Transport Information: | N/A | ||||||||||||||
| PSA: | 0.00000 | ||||||||||||||
| LogP: | 0.74360 | ||||||||||||||
selenophene
2-iodolselenophene
| Conditions | Yield |
|---|---|
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran; hexane at -78 - -30℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -30℃; for 2h; | 99% |
| Stage #1: selenophene With n-butyllithium In diethyl ether at 30 - 50℃; for 0.5h; Inert atmosphere; Stage #2: With iodine In diethyl ether at -78 - 20℃; for 12h; Inert atmosphere; | 95% |
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran Stage #2: With iodine | 55% |
| Conditions | Yield |
|---|---|
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran; hexane at -78 - -30℃; for 2h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -30℃; for 2h; | 98.1% |
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; | 77.5% |
| Stage #1: selenophene With n-butyllithium In diethyl ether; hexane at -10 - 20℃; for 1.5h; Inert atmosphere; Stage #2: tributyltin chloride In diethyl ether; hexane at 20℃; for 1h; Inert atmosphere; | 71% |
selenophene
tetraiodoselenophene
| Conditions | Yield |
|---|---|
| With mercury(II) diacetate; iodine; acetic acid at 95℃; for 0.5h; | 97.4% |
| Stage #1: selenophene With mercury(II) diacetate; iodine; acetic acid at 90℃; Stage #2: With potassium iodide In water at 20℃; for 3h; |
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide In tetrahydrofuran at 20℃; | 95% |
| With N-Bromosuccinimide In chloroform at 20℃; for 10h; Inert atmosphere; Schlenk technique; | 91% |
| With N-Bromosuccinimide In chloroform at 0 - 20℃; for 1h; Inert atmosphere; | 90% |
selenophene
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4,4,5,5-tetramethyl-2-(selenophen-2-yl)-1,3,2-dioxaborolane
| Conditions | Yield |
|---|---|
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.33333h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 94% |
| With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 18h; Inert atmosphere; |
| Conditions | Yield |
|---|---|
| With CF3SO3Ag In dichloromethane under N2 AgOTf was added to a slurry of complex in CH2Cl2, the soln. wasstirred for 2 h, filtered, selenophene was added, stirred for 12 h; filtered, washed with diethyl ether and pentane; elem. anal.; | 93% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; potassium carbonate; triphenylphosphine; Trimethylacetic acid In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; regioselective reaction; | 93% |
| Conditions | Yield |
|---|---|
| Stage #1: selenophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane for 1.5h; Heating / reflux; Stage #2: carbon dioxide In diethyl ether; hexane at 20℃; Cooling with acetone-dry ice; Stage #3: With hydrogenchloride; potassium hydroxide; water more than 3 stages; | 92.1% |
| Conditions | Yield |
|---|---|
| Stage #1: selenophene With n-butyllithium In tetrahydrofuran; hexane at -78 - -30℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; hexane at -30℃; for 2h; | 91.6% |
selenophene
2,3,4,5-tetrabromoselenophene
| Conditions | Yield |
|---|---|
| With bromine; acetic acid In chloroform at 0 - 70℃; for 18h; | 91% |
| With bromine In dichloromethane at 0℃; for 74h; Reflux; Inert atmosphere; | 84% |
| With bromine In dichloromethane at 0℃; Reflux; | 84% |
