193966-77-7

Basic information

• Product Name: 4-BroMophenoxytriisopropylsilane
• Synonyms: 4-BroMophenoxytriisopropylsilane;(4-BroMophenoxy)tris(1-Methylethyl)silane;1-BroMo-4-[[tris(1-Methylethyl)silyl]oxy]benzene;1-BroMo-4-triisopropylsilyloxybenzene
• CAS NO: 193966-77-7
• Molecular Formula: C₁₅H₂₅BrOSi
• Molecular Weight: 329
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 193966-77-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 312.5±25.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 1.159 g/mL at 25 °C
• Refractive Index: n20/D1.522
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 4-BroMophenoxytriisopropylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BroMophenoxytriisopropylsilane(193966-77-7)
• EPA Substance Registry System: 4-BroMophenoxytriisopropylsilane(193966-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 193966-77-7(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Tyramine intermediate.

Upstream product

• 106-41-2 4-bromo-phenol 
• 13154-24-0 triisopropylsilyl chloride 
• 288-32-4 1H-imidazole 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 323575-90-2 9-(4-triisopropylsilanyloxy-phenyl)-9H-fluoren-9-ol 
• 1258785-43-1 3-(4-nitrophenyl)-2-(4-triisopropylsilanyloxyphenyl)-2H-azirine 

Relevant articles and documents

Structurally Divergent Lithium Catalyzed Friedel–Crafts Reactions on Oxetan-3-ols: Synthesis of 3,3-Diaryloxetanes and 2,3-Dihydrobenzofurans

The first examples of 3,3-diaryloxetanes are prepared in a lithium-catalyzed and substrate dependent divergent Friedel–Crafts reaction. para-Selective Friedel–Crafts reactions of phenols using oxetan-3-ols afford 3,3-diaryloxetanes by displacement of the hydroxy group. These constitute new isosteres for benzophenones and diarylmethanes. Conversely, ortho-selective Friedel–Crafts reactions of phenols afford 3-aryl-3-hydroxymethyl-dihydrobenzofurans by tandem alkylation–ring-opening reactions; the outcome of the reaction diverging to structurally distinct products dependent on the substrate regioselectivity. Further reactivity of the oxetane products is demonstrated, suitable for incorporation into drug discovery efforts.

New strategy for the synthesis of proaporphine and homoproaporphine-type alkaloids from a common intermediate

Starting with 3-bromo-4,5-dimethoxybenzaldehyde 14, it was coupled with the boronic anhydride 15 using standard Suzuki reaction conditions to give 16 (91%). The aldehyde 16 was exposed to classical nitro-aldol reaction conditions to give 17 (88%), and conjugatively reduced with DIBAL-H to give 18 (91%). Protection of the amine 18 as its N-carbamate derivative 19, followed by condensation with glycol aldehyde dimer under acidic reaction conditions gave 20 (78%). Subsequent conversion of 20 into its mesylate derivative 21, and exposure to CsF under aprotic reaction conditions gave 22 (81%). Deprotection of 22 gave (±)-stepharine 10 in 29% overall yield though 8 steps. A similar sequence of reaction conditions converted the amine 18 into the -NTs protected homoproaporphine adduct 28.

Boronic acid catalysis as a mild and versatile strategy for direct carbo- and heterocyclizations of free allylic alcohols

BAC to the future: Boronic acid catalysis (BAC) was applied to the direct activation of alcohols leading to the preparation of carbocycles (see scheme), benzofurans, tetrahydrofurans, pyrrolidines, pyrans, piperidines, and various polycyclic compounds. The reactions proceed under mild conditions that circumvent the use of reactive leaving groups like halides. Copyright