1,3-dithian-2-yltrimethylsilane

• ChemBase ID: 149719
• Molecular Formular: C7H16S2Si
• Molecular Mass: 192.41744
• Monoisotopic Mass: 192.04626904
• SMILES: C[Si](C)(C)C1SCCCS1
• Canonical SMILES: C[Si](C1SCCCS1)(C)C
• InChI: InChI=1S/C7H16S2Si/c1-10(2,3)7-8-5-4-6-9-7/h7H,4-6H2,1-3H3
• InChIKey: BTTUMVHWIAXYPJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dithian-2-yltrimethylsilane
• IUPAC Traditional name: 1,3-dithian-2-yltrimethylsilane
• Synonyms: 2-(Trimethylsilyl)-1,3-dithiane; 2-Trimethylsilyl-1,3-dithiane; 2-(三甲基硅基)-1,3-二噻烷; 2-三甲基硅基-1,3-二噻烷

Database IDs

• CAS Number: 13411-42-2
• EC Number: 236-504-4
• MDL Number: MFCD00006655
• Beilstein Number: 1616463
• PubChem SID: 162243881; 24853194
• PubChem CID: 83413

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.2102
• LogD (pH = 7.4): 4.2102
• Log P: 4.2102
• Molar Refractivity: 49.731 cm^3
• Polarizability: 21.956867 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 54-55 °C/0.17 mmHg(lit.); 54-55°C/0.17mm
• Flash Point: 204.8 °F; 96 °C; 96°C(204°F)
• Density: 1.014 g/mL at 25 °C(lit.); 1.040
• Refractive Index: 1.5330; n20/D 1.533(lit.)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥99%; 98+%
• Empirical Formula (Hill Notation): C7H16S2Si

DETAILS

Sigma Aldrich - 220817

Application
A versatile acyl anion equivalent.1,2
Packaging
5, 25 g in glass bottle

REFERENCES

• The lithio-derivative undergoes Peterson-type olefination (see Appendix 4) with aldehydes and ketones to give the ketene dithioacetals, useful intermediates in a variety of reactions: J. Org. Chem., 37, 1926 (1972); J. Chem. Soc., Perkin 1, 2272 (1973); Chem. Ber., 106, 2277 (1973). Further reaction with carbonyl compounds provides, after deprotection, a useful -lactone synthesis. An alternative PhSeCl-promoted ring closure, followed by selenoxide elimination gives the butenolide: J. Org. Chem., 45, 2236 (1980):
  
• For a review of the chemistry of ketene dithioacetals, see: Synthesis, 171 (1990).
• Tandem bis-alkylation with epoxides provides a route to enantiopure 1,5-diols and related compounds; the key step is a [1,4] Brook rearrangement of the initially-formed alkoxide: Synlett, 511 (1994):
  
• Review of the chemistry of mixed organosulfur/organosilicon compounds: Tetrahedron, 44, 281 (1988).