| Identification | More | [Name]
2-TRIMETHYLSILYL-1,3-DITHIANE | [CAS]
13411-42-2 | [Synonyms]
1,3-DITHIAN-2-YLTRIMETHYLSILANE
2-TRIMETHYLSILYL-1,3-DITHIANE
Silane, 1,3-dithian-2-yltrimethyl-
2-TRIMETHYLSILYL-1,3-DITHIANE, 99+%
2-TRIMETHYLSILYL-1,3-DITHIANE 97%
2-Trimethylsilyl-1,3-dithiane, 98+%
1,3-Dithiane-2-yltrimethylsilane | [EINECS(EC#)]
236-504-4 | [Molecular Formula]
C7H16S2Si | [MDL Number]
MFCD00006655 | [Molecular Weight]
192.42 | [MOL File]
13411-42-2.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLORLESS TO SLIGHTLY YELLOW LIQUID | [Boiling point ]
54-55 °C0.17 mm Hg(lit.) | [density ]
1.014 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.533(lit.)
| [Fp ]
205 °F
| [storage temp. ]
2-8°C | [solubility ]
Insol H2O; sol organic solvents. | [form ]
clear liquid | [color ]
Colorless to Light yellow to Light orange | [Specific Gravity]
1.014 | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [BRN ]
1616463 | [CAS DataBase Reference]
13411-42-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
3334 | [WGK Germany ]
3
| [F ]
13 | [TSCA ]
No | [HS Code ]
2934.99.9001 |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLORLESS TO SLIGHTLY YELLOW LIQUID | [Physical properties]
bp 54–55 °C/0.17 mmHg. | [Uses]
2-Trimethylsilyl-1,3-dithiane is the precursor of dithioketene acetals which are good substrates for
both cationic and anionic cyclization processes; the anion reacts with unsaturated ketones and aldehydes to give vinyl dithioketene acetals that can be used as dienes or for the preparation of substituted α,β-unsaturated alkyl ketones; alkylation of the anion provides a general synthesis of acylsilanes. It participates the following reactions: Thioketene Acetals, Cationic and Anionic Cyclizations, Unsaturated Dithioketene Acetals, Acylsilanes, Multicomponent Linchpin Reactions, Formation of Bis(acylsilanes) etc. | [Uses]
A versatile acyl anion equivalent.1,2 | [Preparation]
2-Trimethylsilyl-1,3-dithiane is prepared by alkylation of 2-lithio-1,3-
dithiane with chlorotrimethylsilane (eq 1). | [General Description]
2-(Trimethylsilyl)-1,3-dithiane participates in Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines. It undergoes novel diazo transfer reaction with tosyl azide in hexamethylphosphoramide-THF to yield 2-diazo-1,3-dithiane, which on decomposition yields formal carbene adducts. It is a versatile acyl anion equivalent. | [Purification Methods]
Fractionally distil the dithiane through an efficient column and collect the fractions that have the correct NMR and IR spectra. 1H NMR (CCl4) 6.36 (SiMe3), 9.87 (SCHS) and dithiane H at 7 and 8 (ratio 1:9:4:2) from Me4Si; UV 244nm ( 711), sh 227nm ( 800). [Corey et al. J Am Chem Soc 89 max 434 1967.] |
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