1,3-Dithiane Property

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

Odor Type

alliaceous

Water Solubility 

Soluble in benzene, ether, chloroform and terahydrofuran. Slightly soluble in water.

Sensitive 

Hygroscopic

BRN 

102534

InChIKey

WQADWIOXOXRPLN-UHFFFAOYSA-N

LogP

1.729 (est)

CAS DataBase Reference

505-23-7(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Dithiane(505-23-7)

Safety

Risk Statements 

20/21/22

Safety Statements 

22-24/25

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

RTECS 

JO5070000

F 

13

HazardClass 

4.1

PackingGroup 

III

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H228Flammable solid

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

1,3-Dithiane Chemical Properties,Usage,Production

Chemical Properties

white to pale beige crystals, needles or powder

Uses

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.]