148249-36-9

Basic information

• Product Name: 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE
• Synonyms: 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE;Bromotriisopropylsilylindole;3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE 95+%;1H-Indole, 3-bromo-1-[tris(1-methylethyl)silyl]-
• CAS NO: 148249-36-9
• Molecular Formula: C₁₇H₂₆BrNSi
• Molecular Weight: 352.38
• Product Categories: Indole;Organohalides;Indoles;Si (Classes of Silicon Compounds);Simple Indoles;Si-N Compounds;Trimethylsilylazide, etc.
• Mol File: 148249-36-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 65°C
• Boiling Point: 331.775 °C at 760 mmHg
• Flash Point: 154.452 °C
• Appearance: /
• Density: 1.149 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Freezer
• CAS DataBase Reference: 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE(148249-36-9)
• EPA Substance Registry System: 3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE(148249-36-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 148249-36-9(Hazardous Substances Data)

Usage

General Description

"3-Bromo-1-(triisopropylsilyl)indole" is a chemical compound associated with the indole family, notable for its diverse applications in the field of organic chemistry. The compound is distinguished by the presence of a bromine atom at the third position and a triisopropylsilyl group at the first position on the indole structure, thus forming a derivative. The triisopropylsilyl group acts as a protective group for the indole ring due to its steric hindrance and resistance to a variety of reactions. The bromine atom acts as a good leaving group, enabling synthetic chemists to manipulate and form various compounds using the bromoindole as a starting material. Overall, "3-Bromo-1-(triisopropylsilyl)indole" is a versatile chemical used extensively in organic synthesis.

InChI:InChI=1/C17H26BrNSi/c1-12(2)20(13(3)4,14(5)6)19-11-16(18)15-9-7-8-10-17(15)19/h7-14H,1-6H3

Upstream product

• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 120-72-9 indole 
• 13154-24-0 triisopropylsilyl chloride 
• 146886-51-3 1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine 

Downstream Products

• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 327163-16-6 1-triisopropylsilyl-3-(4-nitro-1,3-butadienyl)indole 
• 135531-86-1 camalexin 
• 208655-73-6 (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid 
• 1365647-67-1 C₄₇H₃₀N₆ 
• 58421-67-3 1-methyl-3-(2-nitrophenyl)-1H-indole 
• 1365647-62-6 C₂₃H₃₀N₂O₂Si 
• 56366-31-5 3-(2-nitrophenyl)-1H-indole 
• 1365647-64-8 C₃₂H₂₁N₃O₂ 
• 1373266-33-1 C₂₆H₁₈N₂O₂ 
• 1373266-34-2 C₂₆H₁₈N₂ 
• 1373266-35-3 C₅₈H₃₈N₄ 
• 1484-19-1 3-ethyl-1H-indole 
• 181780-84-7 Phenyl-(1-triisopropylsilanyl-1H-indol-3-yl)-methanone 

Relevant articles and documents

Direct C-3 lithiation of 1-(triisopropylsilyl)indole

1-(Triisopropylsilyl)indole can be directly lithiated at 3-position with tert-BuLi-TMEDA in hexane at 0°C for 3 h. The generated lithio species is reacted with a variety of electrophiles to give 3-substituted 1-(triisopropylsilyl)indoles in good yields.

NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE

Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the said compound, and the organic electronic device uses the said organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: Asymmetric synthesis of allyl oxindoles

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee. Copyright