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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
assay:
≥90% (GC)

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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.)

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

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General description

Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent[1][2][3] and bulky equivalent of acetate. It participates in syn-selective aldol reactions.[4] It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O.[3] Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield.[5] Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000080451
0000086369
0000002122
1359778V
BGBC0406V

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Varinder K. Aggarwal et al.
The Journal of organic chemistry, 63(21), 7306-7310 (2001-10-24)
Asymmetric oxidation of a range of 1,3-dithianes was studied using the Kagan protocol [CHP (4 equiv), (+)-DET (2 equiv), Ti(OiPr)(4) (1 equiv), and H(2)O (1 equiv) at -35 degrees C for 48 h]. 1,3-Dithiane itself gave monoxide (30% ee) and
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)
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)
Mark Cushman et al.
The Journal of organic chemistry, 67(16), 5807-5816 (2002-08-03)
A series of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-D-ribityllumazine were synthesized as inhibitors of both Escherichia coli riboflavin synthase and Bacillus subtilis lumazine synthase. The compounds were designed to bind to both the ribitylpurine binding site and the phosphate binding
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