1-[tris(propan-2-yl)silyl]-1H-pyrrole

• ChemBase ID: 65420
• Molecular Formular: C13H25NSi
• Molecular Mass: 223.4298
• Monoisotopic Mass: 223.17562634
• SMILES: n1([Si](C(C)C)(C(C)C)C(C)C)cccc1
• Canonical SMILES: CC([Si](n1cccc1)(C(C)C)C(C)C)C
• InChI: InChI=1S/C13H25NSi/c1-11(2)15(12(3)4,13(5)6)14-9-7-8-10-14/h7-13H,1-6H3
• InChIKey: FBQURXLBJJNDBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[tris(propan-2-yl)silyl]-1H-pyrrole
• IUPAC Traditional name: 1-(triisopropylsilyl)pyrrole
• Synonyms: 1-(Triisopropylsilyl)pyrrole; 1-(Triisopropylsilyl)pyrrole; TIPS-pyrrole; 1-(三异丙基硅基)吡咯; 1-(三异丙基硅烷)吡咯

Database IDs

• CAS Number: 87630-35-1
• MDL Number: MFCD00054932
• Beilstein Number: 3540663
• PubChem SID: 24863531; 162031159
• PubChem CID: 145136

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.2829
• LogD (pH = 7.4): 4.2829
• Log P: 4.2829
• Molar Refractivity: 66.1032 cm^3
• Polarizability: 27.577578 Å^3
• Polar Surface Area: 4.93 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 78 °C/0.4 mmHg(lit.); 78°C/0.4mm
• Flash Point: 106°C(222°F); 107 °C; 224.6 °F
• Density: 0.904; 0.904 g/mL at 25 °C(lit.)
• Refractive Index: 1.4920; n20/D 1.492(lit.)

Safety Information

• Storage Warning: IRRITANT; Moisture Sensitive
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20-22-36; 22
• Safety Statements: 26; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302 + H332-H319
• GHS Precautionary statements: P280F; P305 + P351 + P338

Product Information

• Purity: 95%; 97+%
• Empirical Formula (Hill Notation): C13H25NSi

DETAILS

Sigma Aldrich - 377945

Packaging
5, 25 mL in glass bottle
Application
Reagent employed in perfluoroalkylation1,2 and Vilsmeier formylation3 reactions.

REFERENCES

• Valuable intermediate in which the bulky TIPS group promotes regioselective 3-substitution. Bromination, nitration and base-catalyzed acylation all occur regioselectively at the 3-position: Tetrahedron Lett., 24, 3455 (1983). Metallating agents also attack at the 3-position: J. Org. Chem ., 55, 6317 (1990); 57, 1653 (1992). The silyl group is easily removed with F ^-, e.g. TBAF. For a review of synthesis of 3-substituted pyrroles, see: Synthesis, 353 (1985). Compare 1-(Phenylsulfonyl)pyrrole, A11599.