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20462-00-4 - Ethyl 1,3-dithiane-2-carboxylate, 98+% - 2-Carboethoxy-1,3-dithiane - 1,3-Dithiane-2-carboxylic acid ethyl ester - L00663 - Alfa Aesar

L00663 Ethyl 1,3-dithiane-2-carboxylate, 98+%

CAS Number
20462-00-4
Synonyms
2-Carboethoxy-1,3-dithiane
1,3-Dithiane-2-carboxylic acid ethyl ester

Size Price ($) Quantity Availability
5g 76.80
25g 304.00
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Ethyl 1,3-dithiane-2-carboxylate, 98+%

MDL
MFCD00006657
EINECS
243-838-4

Chemical Properties

Formula
C7H12O2S2
Formula Weight
192.30
Melting point
19-21°
Boiling Point
75-77°/0.2mm
Flash Point
54°(129°F)
Density
1.220
Refractive Index
1.5400
Solubility
Slightly miscible with water.

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.

Notes

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

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226

Flammable liquid and vapour.

Precautionary Statements: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1424352
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2934.99
TSCA
No

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