43749
Ethyl 1,3-dithiane-2-carboxylate
technical, ≥90% (GC)
Synonym(s):
Glyoxylic acid ethyl ester trimethylenemercaptal
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About This Item
Empirical Formula (Hill Notation):
C7H12O2S2
CAS Number:
Molecular Weight:
192.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
243-838-4
Beilstein/REAXYS Number:
1424352
MDL number:
Assay:
≥90% (GC)
grade
technical
Quality Segment
assay
≥90% (GC)
refractive index
n20/D 1.539 (lit.), n20/D 1.541
bp
75-77 °C/0.2 mmHg (lit.)
density
1.22 g/mL at 25 °C (lit.)
functional group
ester, thioether
SMILES string
CCOC(=O)C1SCCCS1
InChI
1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
InChI key
ANEDZEVDORCLPM-UHFFFAOYSA-N
General description
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
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