| Identification | More | [Name]
1,3-Dithiane | [CAS]
505-23-7 | [Synonyms]
1,3-DITHIANE
M-DITHIANE
1,3-Dithiacyclohexane
1,3-Dithian
Dithiane-1,3
1,3-Dithiane,99%
1,3-Dithiane,98%
META-DITHIANE
1,3-Dithane
| [EINECS(EC#)]
208-006-7 | [Molecular Formula]
C4H8S2 | [MDL Number]
MFCD00006654 | [Molecular Weight]
120.24 | [MOL File]
505-23-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to pale beige crystals, needles or powder | [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 | [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 | [Detection Methods]
GC,NMR | [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) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 1325 4.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
JO5070000
| [F ]
13 | [HazardClass ]
4.1 | [PackingGroup ]
III | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [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.] |
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