1,2-Bis(chlorodimethylsilyl)ethane Property

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

InChIKey

VGQOKOYKFDUPPJ-UHFFFAOYSA-N

CAS DataBase Reference

13528-93-3(CAS DataBase Reference)

EPA Substance Registry System

Silane, 1,2-ethanediylbis[chlorodimethyl- (13528-93-3)

Safety

Hazard Codes 

C

Risk 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

HS Code 

29319000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

1,2-Bis(chlorodimethylsilyl)ethane Chemical Properties,Usage,Production

Chemical Properties

transparent low melting solid

Physical properties

mp 36–41°C; bp 198°C/734 mmHg.

Uses

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.

Uses

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).