tert-butyl 2-(hydroxydimethylsilyl)-1H-indole-1-carboxylate

• ChemBase ID: 144607
• Molecular Formular: C15H21NO3Si
• Molecular Mass: 291.41764
• Monoisotopic Mass: 291.12907007
• SMILES: CC(C)(C)OC(=O)n1c2ccccc2cc1[Si](C)(C)O
• Canonical SMILES: O=C(n1c2ccccc2cc1[Si](O)(C)C)OC(C)(C)C
• InChI: InChI=1S/C15H21NO3Si/c1-15(2,3)19-14(17)16-12-9-7-6-8-11(12)10-13(16)20(4,5)18/h6-10,18H,1-5H3
• InChIKey: ARJIKJGACIMUOM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-(hydroxydimethylsilyl)-1H-indole-1-carboxylate
• IUPAC Traditional name: tert-butyl 2-(hydroxydimethylsilyl)indole-1-carboxylate
• Synonyms: 2-(hydroxydimethylsilyl)-1,1-dimethylethylindole-1-carboxylic acid ester; N-Boc-indol-2-yldimethylsilanol; N-Boc-2-indolyldimethylsilanol; 1-Boc-2-indolyldimethylsilanol; N-Boc-吲哚-2-基二甲基硅烷醇; N-Boc-2-吲哚基二甲基硅烷醇; 1-Boc-2-吲哚基二甲基硅醇

Database IDs

• CAS Number: 784161-48-4
• MDL Number: MFCD08457643
• PubChem SID: 162238819; 24884947
• PubChem CID: 12130895

CALCULATED PROPERTIES

• Acid pKa: 11.920215
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.1918998
• LogD (pH = 7.4): 2.191887
• Log P: 2.1919
• Molar Refractivity: 74.6384 cm^3
• Polarizability: 32.715904 Å^3
• Polar Surface Area: 51.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: >110 °C; >230 °F
• Refractive Index: n20/D 1.545

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Linear Formula: ((C8H5N)(CO2C(CH3)3))Si(CH3)2(OH)

DETAILS

Sigma Aldrich - 667900

Application
A useful silicon nucleophile for Pd-catalyzed cross-coupling.4
Reactant for:Palladium-catalyzed cross-coupling reactions1,2,3
Packaging
1, 5 g in glass bottle
Protocols & Applications
Cross-Coupling using Organosilanols as Powerful Nucleophiles