13528-93-3

Basic information

• Product Name: 1,2-Bis(chlorodimethylsilyl)ethane
• Synonyms: 1,2-ethanediylbis[chlorodimethyl-silan;1,2-ethanediylbis[chlorodimethyl-Silane;SILANE BM2E;STABASE;2,5-DICHLORO-2,5-DIMETHYL-2,5-DISILAHEXANE;1,2-BIS(CHLORODIMETHYLSILYL)ETHANE;1,2-BIS(DIMETHYLCHLOROSILYL)ETHANE;1,1,4,4-TETRAMETHYL-1,4-DICHLORODISILETHYLENE
• CAS NO: 13528-93-3
• Molecular Formula: C₆H₁₆Cl₂Si₂
• Molecular Weight: 215.27
• EINECS: 236-871-0
• Product Categories: Monochlorosilanes;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 13528-93-3.mol

Chemical Properties

• Melting Point: 35-38 °C(lit.)
• Boiling Point: 198 °C734 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Transparent/Low Melting Solid
• Density: 0.97 g/cm³
• Vapor Pressure: 0.512mmHg at 25°C
• Refractive Index: 1.427
• Storage Temp.: Flammables area
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 1920141
• CAS DataBase Reference: 1,2-Bis(chlorodimethylsilyl)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(chlorodimethylsilyl)ethane(13528-93-3)
• EPA Substance Registry System: 1,2-Bis(chlorodimethylsilyl)ethane(13528-93-3)

Safety Data

• Hazard Codes: C
• Statements: 34-10
• Safety Statements: 26-28-36/37/39-45-16
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 13528-93-3(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
1,2-Bis(chlorodimethylsilyl)ethane is used as a protecting reagent for primary amines, forming tetramethyldisilylazacyclopentane or Stabase adducts. These adducts are stable under strongly basic conditions, making them suitable for use in the alkylation of substrates bearing a primary amine. This application is particularly attractive due to the ease of preparation, base stability, and facile removal of the protecting group.
2. Used in Medicine Field:
In the medical field, 1,2-Bis(chlorodimethylsilyl)ethane can be utilized in the synthesis of various pharmaceutical compounds, taking advantage of its silylating properties and ability to protect primary amines during chemical reactions.
3. Used in Electronics Industry:
The electronics industry can benefit from 1,2-Bis(chlorodimethylsilyl)ethane's properties as a silylating reagent, potentially using it in the development of new materials or components with specific characteristics.
4. Used in Polymer Material:
In the polymer material industry, 1,2-Bis(chlorodimethylsilyl)ethane can be employed to modify polymers or create new materials with enhanced properties, such as improved stability or reactivity.
5. Used in Combination with Zinc:
When combined with zinc, 1,2-Bis(chlorodimethylsilyl)ethane can form organozinc carbenoids, which are valuable intermediates in organic synthesis.
6. Used as an Electrophilic Silylating Reagent:
Due to its reactivity, 1,2-Bis(chlorodimethylsilyl)ethane can also be used as an electrophilic silylating reagent in various chemical reactions, further expanding its applications across different industries.

InChI:InChI=1/C6H16Cl2Si2/c1-9(2,7)5-6-10(3,4)8/h5-6H2,1-4H3

Upstream product

• 17861-43-7 2-(ethyl(dimethyl)silyl)-1-(trimethylsilyl)ethane 
• 75-36-5 acetyl chloride 
• 1066-35-9 dimethylmonochlorosilane 
• 754-05-2 ethenyltrimethylsilane 
• 74485-31-7 1,1,2,2-tetramethyl-1,2-disilacyclobutane 
• 1719-58-0 Chlorodimethylvinylsilane 
• 993-07-7 trimethylsilan 
• 18142-52-4 (2-Chlor-vinyl)-dimethyl-chlorsilan 
• 75-94-5 trichlorovinylsilane 
• 124-70-9 Dichloromethylvinylsilane 
• 75-54-7 Dichloromethylsilane 
• 5356-83-2 ethoxydimethylvinylsilane 

Downstream Products

• 554-68-7 triethylamine hydrochloride 
• 78605-23-9 ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate 
• 78605-28-4 2,2,5,5-Tetramethyl-1-m-tolyl-[1,2,5]azadisilolidine 
• 127801-35-8 chlorodimethyl(2-ethyl)silane 
• 91166-50-6 1,1'-(1,2-ethanediyl)bis 
• 119345-86-7 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2,2,5,5-tetramethyl-[1,2,5]azadisilolidine 
• 78605-27-3 1-(4-Methoxy-phenyl)-2,2,5,5-tetramethyl-[1,2,5]azadisilolidine 
• 78605-24-0 2,2,5,5-Tetramethyl-1-p-tolyl-[1,2,5]azadisilolidine 
• 78616-89-4 1-Cyclohexyl-2,2,5,5-tetramethyl-[1,2,5]azadisilolidine 
• 74485-31-7 1,1,2,2-tetramethyl-1,2-disilacyclobutane 
• 142802-58-2 2,2,5,5,7,7,10,10-Octamethyl-1,6-diaza-2,5,7,10-tetrasilacyclodecan 
• 142802-56-0 2,2,5,5,7,7,10,10,12,12,15,15-Dodecamethyl-1,6,11-triaza-2,5,7,10,12,15-hexasilacyclopentadecan 
• 7418-19-1 2,2,5,5-tetramethyl-1-aza-2,5-disila-cyclo-pentane 
• 7418-20-4 2,2,5,5-tetramethyl-2,5-disila-1-oxacyclopentane 

Relevant articles and documents

Synthesis of unsymmetrical 1,2-bis(diorganochlorosilyl)ethanes

Unsymmetrical 1,2-bis(diorganylsilyl)ethanes were synthesized by two procedures. Hydrosilylation of chloro(vinyl)silanes were used to obtain compounds of the general formula ClMe2SiCH2CH 2SiRMeCl with different substituents (R = Et, Vin, Ph) on the silicon atom. Chlorodealkylation of 1,2-bis(trialkylsilyl)ethanes gave compounds of the general formula ClAlk2SiCH2CH2SiAlk 2Cl (Alk = Me, Et, Pr). It is established that the latter reaction provides high yields only with Me-and Et-substituted compounds, whereas Pr-substituted products are formed in poor yields. The mechamism of this reaction based on quantum-chemical calculations is offered.

Process for the preparation of halogenated 1,2-disilaethanes

A process for the preparation of halogenated 1,2-disilaethanes of the general formula X3?nRnSi—CHR1CHR1—SiRnX3?n??(I) in which R may be identical or different and denotes a hydrogen atom or a monovalent optionally substituted hydrocarbon radical having 1 to 40 carbon atom(s) per radical, R1may be identical or different and denotes a hydrogen atom or a monovalent optionally substituted hydrocarbon radical having 1 to 40 carbon atom(s) per radical, X denotes a halogen atom and n denotes 0, 1 or 2, wherein halogenated 1,2-disilaethenes of the general formula X3?nRnSi—CR1═CR1—SiRnX3?n??(II) in which R, R1, X and n have the meaning stated above therefor, are reacted with hydrogen in the presence of promoting catalysts. The product is produced in high yield and purity.

Organosilicon compound and process for producing organosilicon compound

An organosilicon compound having a Si--C--C--Si bond, a C=C--Si bond and/or a CH--CH--Si bond is prepared by reacting an olefin or a substituted olefin with a disilane in the presence of a platinum-containing catalyst. The resulting compound can be further treated with an alkyl lithium, an aryl lithium or a Grignard reagent.