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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:
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

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
Phase Transfer Catalysis for Preparation and Alkylation of Ethyl 1,3-Dithiane-2-carboxylate.
Lissel M.
Synthetic Communications, 11(4), 343-346 (1981)
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)
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