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1,3-Dithiane, 98%
CAS: 505-23-7 | C4H8S2 | 120.228 g/mol
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Catalog number A10505.22
also known as A10505-22
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504.65
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Quantity:
100 g
Price (USD)
504.65
Online Exclusive
560.00Save 55.35 (10%)
Each
Chemical Identifiers
CAS505-23-7
IUPAC Name1,3-dithiane
Molecular FormulaC4H8S2
InChI KeyWQADWIOXOXRPLN-UHFFFAOYSA-N
SMILESC1CSCSC1
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Specifications
Specification Sheet
Specification SheetAssay (GC)≥97.5%
Appearance (Color)White to pale cream to pale yellow
FormPowder or crystalline powder or crystals or needles
1,3-Dithiane is used in umpolung reactions such as the Corey-Seebach reaction. It acts as a reagent for the deoxygenation of sulfoxides to their corresponding sulfides. Further, it is used as a protecting group for carbonyl compounds used in organic synthesis. It serves as a useful labeled synthon. In addition to this, it is used in the preparation of 2-ethyl-[1,3]dithiane.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
1,3-Dithiane is used in umpolung reactions such as the Corey-Seebach reaction. It acts as a reagent for the deoxygenation of sulfoxides to their corresponding sulfides. Further, it is used as a protecting group for carbonyl compounds used in organic synthesis. It serves as a useful labeled synthon. In addition to this, it is used in the preparation of 2-ethyl-[1,3]dithiane.
Solubility
Soluble in benzene, ether, chloroform and terahydrofuran. Slightly soluble in water.
Notes
Hygroscopic. Incompatible with strong bases and strong oxidizing agents.
1,3-Dithiane is used in umpolung reactions such as the Corey-Seebach reaction. It acts as a reagent for the deoxygenation of sulfoxides to their corresponding sulfides. Further, it is used as a protecting group for carbonyl compounds used in organic synthesis. It serves as a useful labeled synthon. In addition to this, it is used in the preparation of 2-ethyl-[1,3]dithiane.
Solubility
Soluble in benzene, ether, chloroform and terahydrofuran. Slightly soluble in water.
Notes
Hygroscopic. Incompatible with strong bases and strong oxidizing agents.
RUO – Research Use Only
General References:
- The 2-lithio derivative, normally generated with n-BuLi, behaves as a formyl anion equivalent. It has been shown that the rigorous exclusion of atmospheric oxygen minimizes side reactions and is critical in obtaining optimum results in these lithiation procedures: J. Org. Chem., 60, 4258 (1995).
- Monoalkylation of the 2-lithio-derivative and cleavage of the dithiane leads to an aldehyde. Successive dialkylation provides a route to ketones. For reviews of the reversal of the normal reactivity of groups, umpolung, see: Angew. Chem. Int. Ed., 18, 239 (1979), and of the umpolung of carbonyl activity through sulfur-containing reagents: Synthesis, 357 (1977). See also 1,3-Propanedithiol, A15261, 1,3-Dithiolane, L11914, and 1,2-Ethanedithiol, L12865.
- For an example of successive acylation and alkylation of 1,3-dithiane, which can be carried out as a one-pot sequence, see: Synthesis, 625 (1980).
- Reaction with 2-cyclohexenone proceeds via 1,2-addition. For details of this and subsequent cleavage and rearrangement, see: Org. Synth. Coll., 8, 309 (1993):