1,2-Bis(dimethylsilyl)benzene

1,2-Bis(dimethylsilyl)benzene Property

Melting point:

<25°C

Boiling point:

101 °C13 mm Hg(lit.)

Density 

0.898 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.51(lit.)

Flash point:

158 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

color 

Colorless to Light yellow

Specific Gravity

0.898

Water Solubility 

insoluble

Hydrolytic Sensitivity

3: reacts with aqueous base

BRN 

2937027

InChI

InChI=1S/C10H18Si2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8,11-12H,1-4H3

InChIKey

QAUCEYVYCBYVDK-UHFFFAOYSA-N

SMILES

C1([SiH](C)C)=CC=CC=C1[SiH](C)C

CAS DataBase Reference

17985-72-7(CAS DataBase Reference)

Safety

Risk Statements 

36/37/38

Safety Statements 

23-24/25

WGK Germany 

3

F 

10

TSCA 

No

HS Code 

2931.90.9010

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

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

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

1,2-Bis(dimethylsilyl)benzene Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid

Uses

1,2-Bis(dimethylsilyl)benzene is a protecting group-reagent for amines and amino acids forming "benzostabase" derivatives. It is an important raw material and in organic synthesis.

Synthesis

General procedure for the synthesis of 1,2-bis(dimethylsilyl)benzene from dimethylmonochlorosilane and 1,2-dibromobenzene: a condenser was assembled in a dry 50 mL two-necked flask, and stirring bars, magnesium powder (99.9%, 24 mmol), lithium chloride (24 mmol), N,N'-dimethylimidazolidinone (DMI, 20 mL) and chlorodimethylsilane ( 48 mmol). After stirring the reaction mixture for 15 minutes at room temperature, 1,2-dibromobenzene (3 mmol) was added and stirring was continued for 4 hours. After completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution. The sodium bicarbonate and the resulting precipitate were removed by filtration. The filtrate was extracted with hexane (3 x 20 mL), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated by rotary evaporation. The crude product was purified by silica gel column chromatography, and the eluent was pure hexane or hexane/dichloromethane mixed solvent.

References

[1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2495 - 2500
[2] Tetrahedron Letters, 2000, vol. 41, # 34, p. 6611 - 6614
[3] Tetrahedron, 1993, vol. 49, # 43, p. 9855 - 9866
[4] Journal of Organometallic Chemistry, 2018, vol. 854, p. 76 - 86
[5] Tetrahedron, 1991, vol. 47, # 47, p. 9807 - 9822