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HomeProduct name list1,3-Dithiane

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: 2024-11-08 21:13:59
1,3-Dithiane Structural

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)
ghs
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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