4-Bromophenoxytriisopropylsilane
98%
Reagent
Code: #141489
Alias
1-Bromo-4-(triisopropylsilyloxy)benzene; 1-Bromo-4-[tris(1-methyl)silyloxy]benzene
CAS Number
193966-77-7
Properties
Soluble in chloroform and methanol
blur_circular Chemical Specifications
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Molecular Information
Weight
329.35 g/mol
Formula
C₁₅H₂₅BrOSi
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Registry Numbers
MDL Number
MFCD18379230
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Physical Properties
Boiling Point
312.5±25.0 °C(Predicted)
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Storage & Handling
Density
1.159 g/mL at 25 °C
Storage
2-8°C, sealed, dry
description Product Description
4-Bromophenoxytriisopropylsilane is a protected form of 4-bromophenol where the phenolic hydroxyl group is silylated with the triisopropylsilyl (TIPS) group. This bulky protecting group provides excellent steric shielding and chemical stability, allowing selective reactions at the aryl bromide position without affecting the oxygen functionality. The bromine enables versatile cross-coupling reactions (e.g., Suzuki, Heck, or Sonogashira) for constructing complex carbon frameworks. It is widely used as a synthetic intermediate in the preparation of pharmaceuticals, natural products, and agrochemicals, particularly in nucleoside, carbohydrate, and peptide chemistry requiring orthogonal protection strategies. Upon completion of synthetic manipulations, the TIPS group can be selectively removed under mild acidic conditions to reveal the free phenol. In materials science, it serves as a precursor for functionalizing polymers or surfaces with phenolic moieties after deprotection.
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