BIS(TRIMETHYLSILYL) SULFIDE
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
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)
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
- F
- 10-13-21
- TSCA
- Yes
- HazardClass
- 3
- PackingGroup
- II
- HS Code
- 29319090
MSDS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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.]
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BIS(TRIMETHYLSILYL) SULFIDE(3385-94-2)Related Product Information
- IRON SILICIDE
- CALCIUM SILICIDE
- hydroxytrimethylsilane
- MAGNESIUM SILICIDE
- Xenon tetrafluoride
- SILVER(I) SULFIDE
- CALCIUM SULFIDE
- Ferrous sulfide
- ALUMINUM CARBIDE
- Aluminium sulfide
- ZINC NITRIDE
- Boron carbide
- Magnesium nitride
- Silicon nitride
- TITANIUM NITRIDE
- Ethyl 1,3-dithiane-2-carboxylate
- SILICON DISULFIDE
- BIS(TRIMETHYLSILYL) SULFIDE