| Identification | More | [Name]
2-(TRIBUTYLSTANNYL)THIOPHENE | [CAS]
54663-78-4 | [Synonyms]
2-THIENYLTRI-N-BUTYLTIN
2-THIOPHENYLTRI-N-BUTYLTIN
2-(TRIBUTYLSTANNYL)THIOPHENE
TRIBUTYL(2-THIENYL)STANNANE
TRIBUTYL(2-THIENYL)TIN
TRI-N-BUTYL(2-THIENYL)TIN
Thiophenyltrinbutyltin
(2-Thienyl)tributylstannane
2-Thienyltributylstannane
2-Thienyltributyltin(IV) | [Molecular Formula]
C16H30SSn | [MDL Number]
MFCD00192513 | [Molecular Weight]
373.18 | [MOL File]
54663-78-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
197-198 °C | [Boiling point ]
155 °C/0.1 mmHg (lit.) | [density ]
1.175 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.518(lit.)
| [Fp ]
221 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
liquid | [color ]
Clear, almost colourless | [Specific Gravity]
1.175 | [InChI]
InChI=1S/C4H3S.3C4H9.Sn/c1-2-4-5-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3; | [InChIKey]
UKTDFYOZPFNQOQ-UHFFFAOYSA-N | [SMILES]
[Sn](CCCC)(CCCC)(CCCC)C1SC=CC=1 | [CAS DataBase Reference]
54663-78-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R21:Harmful in contact with skin.
R25:Toxic if swallowed.
R36/38:Irritating to eyes and skin .
R48/23/25:Toxic: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S35:This material and its container must be disposed of in a safe way .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2788 6.1/PG 3
| [WGK Germany ]
3
| [TSCA ]
No | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
2-(Tri-n-butylstannyl)thiophene derivative is employed in Stille reaction involving efficient carbon-carbon bond formation. | [Synthesis]
2-Bromothiophene (4.89 g, 30 mmol) and 60 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask with a device constant pressure dropping funnel. The system was evacuated and then displaced three times with argon to remove air. The reaction flask was placed in a cryostat reaction bath and cooled to -20 °C. Subsequently, a n-hexane solution of n-butyllithium (2.2 mol/L, 15 mL, 33 mmol) was slowly added dropwise under argon protection and the temperature was maintained at -20 °C for 1 h of reaction. Next, tributyltin chloride (8.95 mL, 33 mmol) was slowly added dropwise and the reaction was continued at -20 °C for 1 hour. Upon completion of the reaction, the reaction system was slowly brought to room temperature and stirred overnight. After the reaction was terminated, 150 mL of deionized water was added to the reaction flask and extracted three times with dichloromethane (80 mL x 3). The organic layers were combined and washed three times with saturated saline (100 mL x 3). The organic phase was dried overnight over anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated by rotary evaporation and the residue was purified by silica gel column chromatography using a petroleum ether solution containing a small amount of triethylamine as eluent to give 11.08 g of the colorless liquid product 2-tributylmethylstannylthiophene in 90% yield. | [References]
[1] Patent: CN105732680, 2016, A. Location in patent: Paragraph 0021 |
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