BIS(TRIMETHYLSILYL) SULFIDE Property

Boiling point:

164 °C(lit.)

Density 

0.846 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4586(lit.)

Flash point:

79 °F

storage temp. 

Flammables area

solubility 

Miscible with terahydrofuran and toluene.

form 

Liquid

Specific Gravity

0.851

color 

Colorless

Water Solubility 

Soluble in tetrahydrofuran and toluene. Hydrolyzes in water.

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

Sensitive 

Air Sensitive

BRN 

1740046

Stability:

store cold

CAS DataBase Reference

3385-94-2(CAS DataBase Reference)

EPA Substance Registry System

Disilathiane, hexamethyl- (3385-94-2)

Safety

Hazard Codes 

T

Risk Statements 

10-23/24/25

Safety Statements 

36/37/39-45

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10-13-21

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

Precautionary statements

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

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

BIS(TRIMETHYLSILYL) SULFIDE Chemical Properties,Usage,Production

Chemical Properties

clear colorless to slightly yellow liquid

Physical properties

bp 164°C; d 0.846 g cm?3.

Uses

Bis(trimethylsilyl)sulfide is used as a silylating agent in the synthesis of pseudohalides, trifluoroacetate and tetramethylsilyl halides. It is used in the transformation of oxides and chlorides into corresponding sulfides. It is also used in the preparation of dimethyltrisulfane as well as thiones from aldehydes and ketones. Further, it is used as a reducing agent to reduce aromatic nitro compounds to amines.

Uses

Hexamethyldisilathiane may be used in the bis-O-demethylation of dimethoxy aromatic compounds.
It may also be used as a sulfur source in the following conversion:

• Amides and lactams to their corresponding sulfur analogs.
• Allyl alcohols to diallyl sulfides.
• Transition metal halides to metal sulfides.
• Aryl iodides to diaryl sulfides.

Uses

Bis(trimethylsilyl) sulfide (TMS2S) is used to reduce aromatic nitro groups to amines and the oxides of sulfur, selenium, and tellurium. Conditions for nitro group reduction (eq 1) are forcing; however, yields are good. Reactions of TMS2S with primary aliphatic nitro groups result in the formation of the thiohydroxamic acids (eq 2) which can be isolated or carried further to the nitrile. Secondary alkyl nitro derivatives provide oximes. Sulfoxides are reduced to sulfides, selenoxides to selenides, and telluroxides to tellurides. Conditions are mild and work well on both the aliphatic and aromatic oxides.

Purification Methods

Dissolve it in pet ether (b ca 40o), remove the solvent and distil it. Redistil it under atmospheric pressure of dry N2. It is collected as a colourless liquid which solidifies to a white solid in Dry-ice. On standing for several days it turns yellow possibly due to liberation of sulfur. Store it below 4o under dry N2. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4033.]