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43749

Sigma-Aldrich

Ethyl 1,3-dithiane-2-carboxylate

technical, ≥90% (GC)

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Synonym(s):
Glyoxylic acid ethyl ester trimethylenemercaptal
Empirical Formula (Hill Notation):
C7H12O2S2
CAS Number:
Molecular Weight:
192.30
Beilstein/REAXYS Number:
1424352
EC Number:
MDL number:
PubChem Substance ID:
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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1 of 4

This Item
663190414476555568
Ethyl 1,3-dithiane-2-carboxylate technical, ≥90% (GC)

43749

Ethyl 1,3-dithiane-2-carboxylate

Ethyl 5-methylindole-2-carboxylate 97%

663190

Ethyl 5-methylindole-2-carboxylate

Ethyl 3,3-diethoxypropionate 90%, technical grade

414476

Ethyl 3,3-diethoxypropionate

Ethyl 2,3-dichloropropionate 97%

555568

Ethyl 2,3-dichloropropionate

density

1.22 g/mL at 25 °C (lit.)

density

-

density

0.978 g/mL at 25 °C (lit.)

density

1.241 g/mL at 25 °C (lit.)

bp

75-77 °C/0.2 mmHg (lit.)

bp

-

bp

92-93 °C/13 mmHg (lit.)

bp

164-165 °C (lit.)

refractive index

n20/D 1.539 (lit.)

refractive index

-

refractive index

n20/D 1.411 (lit.)

refractive index

n20/D 1.4480 (lit.)

grade

technical

grade

-

grade

-

grade

-

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

signalword

Warning

hcodes

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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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)
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
L.A. Flippin et al.
Tetrahedron Letters, 26, 2977-2977 (1985)
Phase Transfer Catalysis for Preparation and Alkylation of Ethyl 1,3-Dithiane-2-carboxylate.
Lissel M.
Synthetic Communications, 11(4), 343-346 (1981)

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