| Identification | More | [Name]
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE | [CAS]
87630-36-2 | [Synonyms]
3-BroMo-1-(triisopropylsi...
Bromotriisopropylsilylpyrrole
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE
3-Bromo-N-(triisopropylsilyl)pyrrole
1-(TRIISOPROPYLSILYL)-3-BROMO-PYRROLE
3-Bromo-1(triisopropysilyl)pyrrole
3-BroMo-1-triisopropylsilanyl-1H-pyrrole
3-BROMO-1-(TRIISOPROPYLSILYL)-1H-PYRROLE
1-(Triisopropylsilyl)-3-bromo-1H-pyrrole
(3-Bromopyrrol-1-yl)-triisopropyl-silane
3-Bromo-1-(triisopropylsilyl)pyrrole >
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 95+%
(3-Bromo-1H-pyrrole-1-yl)triisopropylsilane
(3-bromopyrrol-1-yl)-tri(propan-2-yl)silane
(3-bromo-1-pyrrolyl)-tri(propan-2-yl)silane
3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole
1H-Pyrrole, 3-broMo-1-[tris(1-Methylethyl)silyl]- | [Molecular Formula]
C13H24BrNSi | [MDL Number]
MFCD01321136 | [Molecular Weight]
302.33 | [MOL File]
87630-36-2.mol |
| Chemical Properties | Back Directory | [Boiling point ]
100 °C(Press: 0.1 Torr) | [density ]
1,16 g/cm3 | [refractive index ]
n20/D1.519 | [Fp ]
>110℃ | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
-5.67±0.70(Predicted) | [color ]
Black | [InChI]
InChI=1S/C13H24BrNSi/c1-10(2)16(11(3)4,12(5)6)15-8-7-13(14)9-15/h7-12H,1-6H3 | [InChIKey]
CNAUTMPRKBSDLH-UHFFFAOYSA-N | [SMILES]
N1([Si](C(C)C)(C(C)C)C(C)C)C=CC(Br)=C1 | [CAS DataBase Reference]
87630-36-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [HS Code ]
2933.99.9701 |
| Hazard Information | Back Directory | [Uses]
3-Bromo-1-(triisopropylsilyl)pyrrole is a pyrrole analogue mainly used in the field of organic synthesis. It can be used to prepare other heterocyclic compounds such as 1-(triisopropylsilyl)pyrrole and 3-Butadienyl-1-tosylpyrroles. | [Synthesis]
General procedure for the synthesis of 3-bromo-1-(triisopropylmethylsilyl)pyrrole from 1-(triisopropylmethylsilyl)pyrrole: at -78 °C, N-bromosuccinimide (NBS, 3.25 g, 18.3 mmol) was slowly added to a 1-(triisopropylmethylsilyl)pyrrole (3.72 g, 16.6 mmol) solution of tetrahydrofuran (THF, 17 mL ) solution was maintained at temperature and stirred continuously for 5 hours. Upon completion of the reaction, hexane (15 mL) and pyridine (0.5 mL) were added to the mixture and stirring was continued for 5 minutes. Subsequently, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=30:1) to finally obtain 3-bromo-1-(triisopropylmethylsilyl)pyrrole (4.67 g, 93% yield) as a colorless oil. | [References]
[1] Chemische Berichte, 1989, vol. 122, p. 169 - 174
[2] Tetrahedron, 2011, vol. 67, # 35, p. 6673 - 6678
[3] Journal of Organic Chemistry, 1984, vol. 49, # 17, p. 3239 - 3240
[4] Tetrahedron, 2004, vol. 60, # 34, p. 7141 - 7146
[5] Organic Letters, 2014, vol. 16, # 24, p. 6334 - 6337 |
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