5624-60-2

Basic information

• Product Name: 1,3,5-TRIS-TRIMETHYLSILANYL-BENZENE
• Synonyms: 1,3,5-TRIS-TRIMETHYLSILANYL-BENZENE;1,3,5-Benzenetriyltris(trimethylsilane);Benzene-1,3,5-triyltris(triMethylsilane)
• CAS NO: 5624-60-2
• Molecular Formula: C₁₅H₃₀Si₃
• Molecular Weight: 294.6552
• Mol File: 5624-60-2.mol
• Article Data: 36

Chemical Properties

• Melting Point: 27-28 °C
• Boiling Point: 244.6°C at 760 mmHg
• Flash Point: 65°C
• Appearance: /
• Density: 0.85g/cm³
• Vapor Pressure: 0.0469mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: 1,3,5-TRIS-TRIMETHYLSILANYL-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRIS-TRIMETHYLSILANYL-BENZENE(5624-60-2)
• EPA Substance Registry System: 1,3,5-TRIS-TRIMETHYLSILANYL-BENZENE(5624-60-2)

Safety Data

• Hazardous Substances Data: 5624-60-2(Hazardous Substances Data)

Usage

Appearance

White to off-white solid

Molecular weight

280.61 g/mol

Function

Used as a protecting group in organic synthesis

Purpose

Stabilizes reactive groups within a molecule and prevents unwanted reactions

Application

Precursor in the synthesis of various organic compounds and pharmaceuticals

Stability

Highly stable and inert compound

Importance

Considered an important tool in the field of organic chemistry

InChI:InChI=1/C15H30Si3/c1-16(2,3)13-10-14(17(4,5)6)12-15(11-13)18(7,8)9/h10-12H,1-9H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 626-39-1 1,3,5-trisbromobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 24886-73-5 1-Azidoadamantane 
• 108-70-3 1,3,5-trichlorobenzene 
• 754-05-2 ethenyltrimethylsilane 
• 100-42-5 styrene 
• 116103-20-9 1-iodoethenyl(trimethyl)silane 

Downstream Products

• 758695-82-8 1,3,5-tris(dibromoboryl)benzene 
• 89641-21-4 benzene-1,3,5-triyltriboronic acid 
• 937009-97-7 3-iodo-5-[(trimethylsilyl)ethynyl]benzoic acid 
• 1375061-53-2 C₂₂H₃₄INO₅Si 
• 1375061-52-1 C₂₂H₃₄INO₅Si 
• 328934-01-6 1,3,5-Tris(diiodoboryl)benzene 
• 125973-71-9 methyl 4-<<3,5-bis(trimethylsilyl)phenyl>carboxamido>benzoate 
• 125973-69-5 methyl 4-<<3,5-bis(trimethylsilyl)phenyl>carbamoyl>benzoate 
• 125973-58-2 (E)-4-<3-<3,5-bis(trimethylsilyl)phenyl>-3-oxo-1-propenyl>benzoic acid 
• 125973-50-4 4-<<3,5-bis(trimethylsilyl)phenyl>carbamoyl>benzoic acid 
• 125973-56-0 Amsilarotene 
• 125973-57-1 (E)-4-<3-oxo-3-<3-(trimethylsilyl)phenyl>-1-propenyl>benzoic acid 
• 948552-39-4 3,5-Bis-trimethylsilanyl-benzoyl chloride 
• 125973-49-1 3,5-bis(trimethylsilyl)aniline 

Relevant articles and documents

Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes

Herein we report a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)2 complex in situ generated from NiCl2·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established.

Iron-catalyzed regioselective cyclotrimerization of alkynes to benzenes

We report the synthesis and characterization of simple di(aminomethyl)pyridine ligated iron-pincer complexes, which catalyzed the regioselective [2+2+2] cyclotrimerization of terminal aryl and alkyl alkynes to provide the 1,2,4-trisubstituted benzene molecules. Interestingly, internal alkynes also exhibited similar cyclization and resulted in hexa-substituted benzene compounds. Increased steric bulk on pincer ligands diminished the selectivity for cycloaddition. Cyclotrimerization reactions proceeded at room temperature upon activation of catalyst by a Grignard reagent. EPR studies indicated thermally induced spin crossover effect in catalyst.

Synthesis of a highly crystalline, covalently linked porous network

Porous networks are described linked by boronates. Also described are processes for producing the porous networks. The porous networks are formed by reacting a polyboronic acid with itself or with a polydiol, a polydiamine, or a polyamino alcohol. The res