1,3-Dithiane
- CAS NO.:505-23-7
- Empirical Formula: C4H8S2
- Molecular Weight: 120.24
- MDL number: MFCD00006654
- EINECS: 208-006-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is 1,3-Dithiane?
Chemical properties
white to pale beige crystals, needles or powder
The Uses of 1,3-Dithiane
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.
Definition
ChEBI: 1,3-dithiane is a dithiane.
Reactions
1,3-dithiane has 2 weakly acidic protons that can be removed and alkylation of the carbon is possible. Once alkylated, the 1,3-dithiane becomes a “protected” carbonyl as it can be hydrolyzed to the corresponding carbonyl structure. Alternatively, the 1,3-dithiane moiety may also be introduced by thioacetalisation of a carbonyl group, either using acid or Lewis acid catalysis, 12 or of a 1,1-dihalide (using transition metal catalysis).
Synthesis Reference(s)
Tetrahedron Letters, 29, p. 4477, 1988 DOI: 10.1016/S0040-4039(00)80527-4
General Description
1,3-Dithiane, a protected formaldehyde anion equivalent, serves as useful labeled synthon.
Purification Methods
Crystallise the 1,3-dithiane from 1.5 times its weight of MeOH at 0o, and sublime it at 40-50o/0.1mm. [Groel & Seebach Synthesis 357 1977, Beilstein 19/1 V 13.]
Properties of 1,3-Dithiane
Melting point: | 52-54 °C (lit.) |
Boiling point: | 207-208°C |
Density | 1.062 (estimate) |
refractive index | 1.5981 (estimate) |
Flash point: | 195 °F |
storage temp. | Inert atmosphere,Room Temperature |
form | Crystals, Needles or Powder |
pka | 31(at 25℃) |
color | White to pale beige |
Odor | at 0.01 % in propylene glycol. alliaceous roasted |
Water Solubility | Soluble in benzene, ether, chloroform and terahydrofuran. Slightly soluble in water. |
Sensitive | Hygroscopic |
BRN | 102534 |
CAS DataBase Reference | 505-23-7(CAS DataBase Reference) |
NIST Chemistry Reference | 1,3-Dithiane(505-23-7) |
Safety information for 1,3-Dithiane
Signal word | Warning |
Pictogram(s) |
Flame Flammables GHS02 |
GHS Hazard Statements |
H228:Flammable solids |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P240:Ground/bond container and receiving equipment. P241:Use explosion-proof electrical/ventilating/lighting/…/equipment. P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for 1,3-Dithiane
InChIKey | WQADWIOXOXRPLN-UHFFFAOYSA-N |
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