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HomeProduct name list1,2-Bis(chlorodimethylsilyl)ethane

1,2-Bis(chlorodimethylsilyl)ethane

Synonym(s):1,1,4,4-Tetramethyl-1,4-dichloro-disilethylene;2,5-Dichloro-2,5-dimethyl-2,5-disilahexane

  • CAS NO.:13528-93-3
  • Empirical Formula: C6H16Cl2Si2
  • Molecular Weight: 215.27
  • MDL number: MFCD00000505
  • EINECS: 236-871-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-23 13:52:06
1,2-Bis(chlorodimethylsilyl)ethane Structural

What is 1,2-Bis(chlorodimethylsilyl)ethane?

Chemical properties

transparent low melting solid

Physical properties

mp 36–41°C; bp 198°C/734 mmHg.

The Uses of 1,2-Bis(chlorodimethylsilyl)ethane

1,2-Bis(chlorodimethylsilyl)ethane can be used as a reagent for the protection of primary amines as their tetramethyldisilylazacyclopentane or Stabase adducts; used in combination with zinc to form organozinc carbenoids; electrophilic silylating reagent.
Protection of Primary Amines.
Few protecting groups exist for the N,N-diprotection of primary amines. The tetramethyldisilylazacyclopentane or Stabase adduct (3) is particularly attractive for this purpose due to its ease of preparation, base stability and facile removal. This cyclic disilane is easily prepared (eq 1) from the commercially available title reagent (1).For primary amines with pKa values between 10 and 11, typical reaction conditions involve the treatment of a dichloromethane solution of the amine with (1) in the presence of two equivalents of triethylamine at room temperature. Subsequent workup with aqueous dihydrogen phosphate provides (3) in excellent yields.1 Stabase adducts are quite stable to strongly basic conditions such as n-butyllithium and s-butyllithium (at ?25°C), lithium diisopropylamide, and Grignard reagents making it a superb candidate for use in the alkylation of substrates bearing a primary amine. For example, protected amino acid derivatives are easily alkylated (eq 2).After formation of the lithium enolate of the protected ethyl glycinate (4) under standard conditions, exposure to various alkyl halides or aldehydes yields alkylation products such as (5).Reactions of 1,2-Bis(chlorodimethylsilyl)ethane

The Uses of 1,2-Bis(chlorodimethylsilyl)ethane

1,2-Bis(chlorodimethylsilyl)ethane is used as Protecting Reagent for Primary Amines. It is also used in Medicine field, electronics industry and polymer material.

Properties of 1,2-Bis(chlorodimethylsilyl)ethane

Melting point: 35-38 °C (lit.)
Boiling point: 198 °C/734 mmHg (lit.)
Density  0.99
Flash point: 155 °F
storage temp.  Inert atmosphere,Room Temperature
form  Low Melting Solid
color  Transparent
Water Solubility  Reacts with water.
Sensitive  Moisture Sensitive
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
BRN  1920141
CAS DataBase Reference 13528-93-3(CAS DataBase Reference)
EPA Substance Registry System Silane, 1,2-ethanediylbis[chlorodimethyl- (13528-93-3)

Safety information for 1,2-Bis(chlorodimethylsilyl)ethane

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P363:Wash contaminated clothing before reuse.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 1,2-Bis(chlorodimethylsilyl)ethane

InChIKey VGQOKOYKFDUPPJ-UHFFFAOYSA-N

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