1578-29-6

Basic information

• Product Name: 2,5-BIS(TRIMETHYLSILYL)FURAN
• Synonyms: 2,5-BIS(TRIMETHYLSILYL)FURAN;trimethyl-(5-trimethylsilyl-2-furyl)silane;trimethyl-(5-trimethylsilylfuran-2-yl)silane;2,5-Bis(trimethylsilyl)furane
• CAS NO: 1578-29-6
• Molecular Formula: C₁₀H₂₀OSi₂
• Molecular Weight: 212.4362
• Mol File: 1578-29-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 182.9 °C at 760 mmHg
• Flash Point: 64.4 °C
• Appearance: /
• Density: 0.87 g/cm³
• CAS DataBase Reference: 2,5-BIS(TRIMETHYLSILYL)FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-BIS(TRIMETHYLSILYL)FURAN(1578-29-6)
• EPA Substance Registry System: 2,5-BIS(TRIMETHYLSILYL)FURAN(1578-29-6)

Safety Data

• Hazardous Substances Data: 1578-29-6(Hazardous Substances Data)

Usage

General Description

2,5-Bis(trimethylsilyl)furan is a chemical compound with the molecular formula C14H26O2Si2. It is a colorless liquid that is primarily used as a reagent in organic synthesis. It is commonly employed as a protective group for alcohols and a source of the furan ring system in organic chemistry. 2,5-Bis(trimethylsilyl)furan is also used in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It is known for its ability to efficiently introduce the furan ring into various organic molecules, making it a valuable tool in the synthesis of complex organic compounds. Additionally, this compound is also used as a solvent in various chemical reactions.

InChI:InChI=1/C10H20OSi2/c1-12(2,3)9-7-8-10(11-9)13(4,5)6/h7-8H,1-6H3

Upstream product

• 1578-33-2 2-furyltrimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 32460-00-7 2,5-dibromofuran 
• 259109-99-4 Bernsteinsaeure-bis-(trimethylsilyl)-ester 
• 110-00-9 furan 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 259109-93-8 C₁₆H₃₄S₄Si₂ 

Downstream Products

• 85925-34-4 Toluene-4-sulfonatebiphenyl-4-yl-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-32-2 Toluene-4-sulfonate(4-iodo-phenyl)-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-30-0 Toluene-4-sulfonate(4-bromo-phenyl)-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-28-6 Toluene-4-sulfonate(4-chloro-phenyl)-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-26-4 Toluene-4-sulfonate(4-fluoro-phenyl)-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-20-8 (o-tolyl)<5-(trimethylsilyl)-2-furyl>iodonium tosylate 
• 85925-24-2 Toluene-4-sulfonatep-tolyl-(5-trimethylsilanyl-furan-2-yl)-iodonium; 
• 85925-22-0 (m-tolyl)<5-(trimethylsilyl)-2-furyl>iodonium tosylate 
• 85925-18-4 Toluene-4-sulfonatephenyl-(5-trimethylsilanyl-furan-2-yl)-iodonium; 

Relevant articles and documents

Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers

Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to the synthesis of arylborane molecules 4a-c, oligomers 8a,b, and polymers 8a′,b′. Photophysical investigations, supported by TD-DFT calculations, reveal highly effective π-conjugation in thienyl- and furylborane species; the latter are also highly emissive.

First synthesis of 1,4-bis(acylsilanes)

1,4-Bis(acylsilanes) were prepared by substitution of 1,2-bis(triflates) with 2-lithio-2-trimethylsilyl- 1,3-dithiane or by silylation of 1,2- bis([1,3]dithian-2-yl)ethane and dethioketalization with methyl iodide or mercuric salts. The reaction with 1,2-dihalogenated alkanes gave dehydrodimers of 2-trialkylsilyl-1,3-dithianes. The cyclodehydration of the 1,4-bis(trialkylsilyl)- 1,4-butanediones gave 2,5-bis(trialkylsilyl) furanes.

Synthesis of symmetrical and unsymmetrical 2,5-bis(trialkylsilyl)furans and 2,6-bis(trialkylsilyl)-4H-pyrans from 1,4- and 1,5-bis(acylsilanes)

2,5-Bis(trialkylsilyl)furans and 2,6-bis(trialkylsilyl)-4Hpyrans have been synthesized by cyclodehydration of 1,4- and 1,5-bis(acylsilanes) under p-toluenesulfonic acid catalysis. The 1,4-bis(acylsilanes) have been prepared from 1,2-bis(1,3-dithian-2yl)ethane according to the reaction sequence metallation-silylationdethioketalization. The 1,5-bis(acylsilanes) have been prepared from 1,3-bis(1,3-dithian-2-yl)propane by a similar strategy or from a S(N) reaction of 1,3-dihalopropanes with 2-trialkylsilyl-2-lithio- 1,3dithiane and deprotection. The method allows efficient preparation of symmetrical as well as unsymmetrical bis(silylated) heterocycles.