Ethyl 1,3-dithiane-2-carboxylate, 98+%

Name: Ethyl 1,3-dithiane-2-carboxylate, 98+%
SKU: L00663.14

CAS: 20462-00-4 | C7H12O2S2 | 192.291 g/mol

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Catalog number L00663.14

also known as L00663-14

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25 g

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Chemical Identifiers

CAS20462-00-4

IUPAC Nameethyl 1,3-dithiane-2-carboxylate

Molecular FormulaC7H12O2S2

InChI KeyANEDZEVDORCLPM-UHFFFAOYSA-N

SMILESCCOC(=O)C1SCCCS1

Specifications

Specification Sheet

FormLiquid

Refractive Index1.5280-1.5420 @ 20?C

Appearance (Color)Clear colorless to pale yellow

Assay (GC)>98.0%

Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.

Solubility
Slightly miscible with water.

Notes
Incompatible with acids, bases, oxidizing agents and reducing agents.

RUO – Research Use Only

General References:

Alkylation of the anion provides a route to ɑ-keto acids (by dethioketalization with NBS), or to substituted acetic acids (by desulfurization): J. Org. Chem., 37, 505 (1972). For phase-transfer alkylation using allylic bromides, see: Liebigs Ann. Chem., 1589 (1982). With crotyl bromide, approx. 95% allylic rearrangement occurs.
The lithiated derivative undergoes 1,4- (Michael) addition to a variety of ɑß-unsaturated compounds. However, the Mg derivative prepared by metallation with an alkylmagnesium halide gives an allylic alcohol by 1,2-addition: Chem. Ber., 114, 2924 (1981).
Pathak, R. B.; Dobson, B. C.; Ghosh, N.; Ageel, K. A.; Alshawish, M. R.; Saruengkhanphasit, R.; Coldham, I. Synthesis of the tricyclic core of manzamine A. Org. Biomol. Chem. 2015, 13 (11), 3331-3340.
Gaggero, N.; Albanese, D. C. M.; Nava, D. A new approach to 4,6-disubstituted-3,4-dihydropyran-2-ones by Domino Michael addition-cyclization reaction under PTC conditions. Tetrahedron 2014, 70 (45), 8744-8749.