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BIS(TRIMETHYLSILYL) SULFIDE

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BIS(TRIMETHYLSILYL) SULFIDE Basic information

Product Name:
BIS(TRIMETHYLSILYL) SULFIDE
Synonyms:
  • 1,1,1,3,3,3-HEXAMETHYLDISILATHIANE
  • BIS(TRIMETHYLSILYL) SULFIDE
  • HEXAMETHYLDISILTHIANE
  • HEXAMETHYLDISILATHIANE
  • THIOBIS(TRIMETHYLSILANE)
  • Bis(trimethylsilyl)sulfur
  • Disilathiane,hexamethyl-
  • Disilthiane, hexamethyl-
CAS:
3385-94-2
MF:
C6H18SSi2
MW:
178.44
EINECS:
222-201-4
Product Categories:
  • Chemical Synthesis
  • Organometallic Reagents
  • Sulfur Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Organosilicon
  • Others
Mol File:
3385-94-2.mol
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BIS(TRIMETHYLSILYL) SULFIDE Chemical Properties

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)
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Safety Information

Hazard Codes 
T
Risk Statements 
10-23/24/25
Safety Statements 
36/37/39-45
RIDADR 
UN 1993 3/PG 3
WGK Germany 
3
10-13-21
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29319090

MSDS

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BIS(TRIMETHYLSILYL) SULFIDE Usage And Synthesis

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.]

BIS(TRIMETHYLSILYL) SULFIDESupplier

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