18412-14-1

Basic information

• Product Name: (benzene-1,2-diyldimethanediyl)bis(trimethylsilane)
• CAS NO: 18412-14-1
• Molecular Formula: C₁₄H₂₆Si₂
• Molecular Weight: 250.5272
• Mol File: 18412-14-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 273.5°C at 760 mmHg
• Flash Point: 101.2°C
• Density: 0.856g/cm³
• Vapor Pressure: 0.00956mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: (benzene-1,2-diyldimethanediyl)bis(trimethylsilane)(CAS DataBase Reference)
• NIST Chemistry Reference: (benzene-1,2-diyldimethanediyl)bis(trimethylsilane)(18412-14-1)
• EPA Substance Registry System: (benzene-1,2-diyldimethanediyl)bis(trimethylsilane)(18412-14-1)

Safety Data

• Hazardous Substances Data: 18412-14-1(Hazardous Substances Data)

Usage

Description

(Benzene-1,2-diyldimethanediyl)bis(trimethylsilane), with the molecular formula C18H32Si2, is an organosilicon compound that features a unique structure comprising silicon, carbon, and hydrogen atoms. This versatile compound is known for its stability and reactivity, making it a valuable component in various chemical and industrial applications.

Uses

Used in Organic Synthesis:
(Benzene-1,2-diyldimethanediyl)bis(trimethylsilane) is utilized as a reagent in organic synthesis, where it plays a crucial role in the formation of complex organic molecules. Its unique structure allows for a wide range of reactions, making it a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Industrial Material Production:
This organosilicon compound is also employed in the production of various industrial materials, such as plastics, rubber, and coatings. Its ability to enhance the properties of these materials, including their thermal stability, mechanical strength, and resistance to environmental factors, makes it a sought-after additive in the manufacturing process.
Used as a Coupling Agent in Polymers and Composites:
(Benzene-1,2-diyldimethanediyl)bis(trimethylsilane) serves as an effective coupling agent in the formulation of polymers and composite materials. Its presence improves the interfacial adhesion between the different components, resulting in enhanced mechanical properties and overall performance of the final product.
Used in the Development of Functional Materials:
Due to its unique structure and properties, (benzene-1,2-diyldimethanediyl)bis(trimethylsilane) has potential applications as a building block for the development of new functional materials. These materials could find use in various high-tech industries, such as electronics, aerospace, and energy storage.
Used as a Protective Coating:
This organosilicon compound also has potential applications as a protective coating for various surfaces. Its ability to form a stable, durable, and resistant layer makes it an ideal candidate for coating applications, where it can provide protection against corrosion, wear, and other forms of degradation.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 91-13-4 α,α'-dibromo-o-xylene 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 95-50-1 1,2-dichloro-benzene 
• 2808-75-5 2-methyl-1-methylenecyclohexane 
• 612-12-4 o-Xylylene dichloride 
• 101270-37-5 O-(2-N,N-diethylcarbamoyloxy)phenyl N,N-diethylcarbamate 
• 95-47-6 o-xylene 
• 59305-27-0 α,.alpha'.-dilithio-o-xylene 
• 84457-41-0 α,alpha'.-bis(trimethylstannyl)-o-xylene 

Downstream Products

• 82452-62-8 1-(Bis-trimethylsilanyl-methyl)-2-trimethylsilanylmethyl-benzene 

Relevant articles and documents

Novel organoborane Lewis acids via selective boron-tin exchange processes - Steric constraints to electrophilic initiation by the boron halide

With the purpose of preparing novel mono- and bidentate organoboron Lewis acids, the scope and limitations of synthesizing the requisite organoboranes by the boron-tin exchange between a boron halide and the appropriate organostannane have been examined in detail. The following organotin derivatives have been obtained either from the corresponding RMgBr or RLi reagent and MenSnCl4-n or from a Barbier procedure using the organic halide, Me3SnCl and magnesium metal: 1,2-bis(trimethylstannyl)ethyne, o-, m-, and p-bis(trimethylstannyl)benzenes, α,o-bis(trimethylstannyl)toluene, α,α-bis(trimethylstannyl)-o-xylene, and 2,2-dimethyl-2-stannaindane. The individual interaction of the 1,2-bis(trimethylstannyl)ethyne and the isomeric bis(trimethylstannyl)benzenes with Et2BBr produced the corresponding bis(diethylboryl)-derivatives. By contrast, with Et2BCl the α,o-bis(trimethylstannyl)toluene gave only o-diethylboryl-α-trimethylstannyltoluene and with BCl3 the α,α′-bis(trimethylstannyl)-o-xylene formed only α,α′-bis-(chlorodimethylstannyl)-o-xylene. Furthermore, in the attempted double boron-tin exchange between o-bis(trimethylstannyl)benzene and BCl3, an unprecedented rearrangement of the 1-(dichloroboryl)-2-(trimethylstannyl)benzene intermediate into its 1-[chloro(methyl)boryl]-2-(chlorodimethylstannyl) isomer was observed. Likewise, o-bis(trimethylstannyl)benzene with PhBCl2 produced by a similar rearrangement 1-[methyl(phenyl)boryl]-2-(chloro-dimethylstannyl)benzene. The thermolysis of such boranes led variously to definite dimers or ill-defined oligomers. Preliminary studies of the properties of these organoboranes have identified the heightened Lewis acidity of 1,2-bis(diethylboryl)ethyne and the π-electron delocalization involving the 2pΖ-boron orbitals in the 9,10-dihydro-9,10-diboraanthracene system. Finally, an electronic mechanism for the boron-tin exchange has been developed to account for the selectivity of the boron halide's attack at unsaturated carbon-tin bonds.

Ni(0)-Catalyzed Cross Coupling of Aryl O-Carbamates and Aryl Triflates with Grignard Reagents. Directed Ortho Metalation-Aligned Synthetic Methods for Polysubstituted Aromatics via a 1,2-Dipole Equivalent

The first Ni(0)-catalyzed cross-coupling reactions of aryl O-carbamates and aryl triflates with Grignard reagents (Scheme I) to give diversely polysubstituted aromatics 2d and 2e (Table I) which feature regiospecificity based on directed ortho metalation (carbamate), minimal β-hydride elimination (triflate), and dependence on steric and electronic effects are described.

The Metallation-Elimination Reaction, II. Monocyclic Anions and Polyanions

Equimolar mixtures of n-butyllithium and potassium tert-amyloxide effect metallation and metal hydride elimination of cyclic olefins directly to give conjugated anions and polyanions in a single operation. 1-Methyl-1-cycloalkenes or methylenecycloalkanes are particularly well suited and give highly unsaturated products.Odd-membered rings eliminate better than their even-membered counterparts, and eight-membered rings eliminate particularly slowly.Reactions with methyl iodide and trimethylsilyl chloride proceed smoothly in high yield.