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43749

Sigma-Aldrich

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:
20462-00-4
Molecular Weight:
192.30
Beilstein/REAXYS Number:
1424352
EC Number:
243-838-4
MDL number:
MFCD00006657
UNSPSC Code:
12352100
PubChem Substance ID:
24867377
NACRES:
NA.22

grade

technical

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.)

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

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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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

131.0 °F - closed cup

flash_point_c

55 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Convenient synthesis of α-keto esters.
Eliel EL and Hartmann AA.
The Journal of Organic Chemistry, 37(3), 505-506 (1972)
Aldol condensations of ethyl 1,3-dithiolane-2-carsoxylate and ethyl 1, 3-dithiane-2-carboxylate with chiral aldehydes. Exceptional diastereoface selectivity from two convenient acetate equivalents.
Flippin LA and Dombroski MA.
Tetrahedron Letters, 26(25), 2977-2980 (1985)
Phase Transfer Catalysis for Preparation and Alkylation of Ethyl 1,3-Dithiane-2-carboxylate.
Lissel M.
Synthetic Communications, 11(4), 343-346 (1981)
Alkylation of the carbanion from methyl bis (ethylthio) acetate with alkyl and aralkyl halides.
Lerner LM.
The Journal of Organic Chemistry, 41(12), 2228-2229 (1976)
Dianions of glyoxylic acid thioketals: conventent α-keto acid equivalents.
Bates GS and Ramaswamy S.
Canadian Journal of Chemistry, 58(7), 716-722 (1980)
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