1,3-Dithiane

1,3-Dithiane
  • CAS No.:505-23-7
Other grades of this product :
1,3-Dithiane Basic information
Product Name:1,3-Dithiane
Synonyms:1,3-Dithiacyclohexane;1,3-Dithian;Dithiane-1,3;M-DITHIANE;1,3-DITHIANE;1,3-Dithiane,98%;1,3-Dithiane,99%;META-DITHIANE
CAS:505-23-7
MF:C4H8S2
MW:120.24
EINECS:208-006-7
Product Categories:Allium sativum (Garlic);Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Nutrition Research;Phytochemicals by Plant (Food/Spice/Herb);Sulfur;Miscellaneous;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Heterocyclic Building Blocks;Others;S-Containing
Mol File:505-23-7.mol
1,3-Dithiane Chemical Properties
Melting point 52-54 °C (lit.)
Boiling point 207-208°C
density 1.062 (estimate)
refractive index 1.5981 (estimate)
Fp 195 °F
storage temp. Inert atmosphere,Room Temperature
form Crystals, Needles or Powder
pka31(at 25℃)
color White to pale beige
Water Solubility Soluble in benzene, ether, chloroform and terahydrofuran. Slightly soluble in water.
Sensitive Hygroscopic
BRN 102534
InChIKeyWQADWIOXOXRPLN-UHFFFAOYSA-N
CAS DataBase Reference505-23-7(CAS DataBase Reference)
NIST Chemistry Reference1,3-Dithiane(505-23-7)
Safety Information
Risk Statements 20/21/22
Safety Statements 22-24/25
RIDADR UN 1325 4.1/PG 2
WGK Germany 3
RTECS JO5070000
13
HazardClass 4.1
PackingGroup III
HS Code 29349990
MSDS Information
ProviderLanguage
m-Dithiane English
SigmaAldrich English
ACROS English
ALFA English
1,3-Dithiane Usage And Synthesis
Chemical Propertieswhite to pale beige crystals, needles or powder
Uses1,3-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.
Reactions1,3-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 Description1,3-Dithiane, a protected formaldehyde anion equivalent, serves as useful labeled synthon.
Purification MethodsCrystallise 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.]
1,3-Dithiane Preparation Products And Raw materials
Raw materialsAcetic acid-->Potassium hydroxide solution-->Dimethoxymethane
Preparation ProductsMETHYL 2-PENTYNOATE

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