| Identification | More | [Name]
BIS(TRIMETHYLSILYL) SULFIDE | [CAS]
3385-94-2 | [Synonyms]
1,1,1,3,3,3-HEXAMETHYLDISILATHIANE
BIS(TRIMETHYLSILYL) SULFIDE
HEXAMETHYLDISILATHIANE
HEXAMETHYLDISILTHIANE
THIOBIS(TRIMETHYLSILANE)
Bis(trimethylsilyl)sulfur
Disilathiane,hexamethyl-
Disilthiane, hexamethyl-
Disilthiane,hexamethyl-
hexamethyl-disilathian
Hexamethyldisilthian
Hexamethyldisilylsulfide
Hexamethyldisilylthiane
BIS(TRIMETHYLSILYL) SULFIDE 95+%
Bis(trimethylsilyl)sulfide,TechnicalGrade
Bis(trimethylsilylsulfide)Hexamethyldisilthiane
Bis(trimethylsilyl)sulfide, GC 95%
Bis(trimethylsilyl)sulfide, tech.
1,1,1,3,3,3-Hexamethylpropanedisilathiane
Hexamethylpropanedisilathiane | [EINECS(EC#)]
222-201-4 | [Molecular Formula]
C6H18SSi2 | [MDL Number]
MFCD00014851 | [Molecular Weight]
178.44 | [MOL File]
3385-94-2.mol |
| Questions And Answer | Back Directory | [Synthesis]
Bis(trimethylsilyl)sulfide can be prepared in one step from Li₂S and TMS chloride. The specific steps are as follows: TMS chloride (50.8 mL, 0.40 mol) is added to a magnetically stirred suspension of anhydrous Li₂S (9.19 g, 0.20 mol) in anhydrous THF (40 mL). The mixture is stirred under dry argon for 25 hours. GC analysis of aliquots of the supernatant at this time shows bis(trimethylsilyl)sulfide (87%), siloxane (4.1%), and unreacted TMS chloride (9.2%). A small Vigreaux column with a vacuum jacket is fitted to the reaction flask, and THF is removed by distillation under argon. The pressure is then reduced, and after a short pre-distillation, the bis(trimethylsilyl)sulfide is collected as a clear, colorless liquid (29.7 g, 83%).
 |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid | [Boiling point ]
164 °C(lit.)
| [density ]
0.846 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4586(lit.)
| [Fp ]
79 °F
| [storage temp. ]
Flammables area | [solubility ]
Miscible with terahydrofuran and toluene. | [form ]
Liquid | [color ]
Colorless | [Specific Gravity]
0.851 | [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 Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R10:Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
10-13-21 | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly yellow liquid | [Physical properties]
bp 164°C; d 0.846 g cm?3. | [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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