Ethyl 1,3-dithiane-2-carboxylate Chemical Properties

Melting point:

19-21°C

Boiling point:

75-77 °C/0.2 mmHg (lit.)

Density 

1.22 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.539(lit.)

Flash point:

130 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

Slightly miscible with water.

BRN 

1424352

InChI

InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3

InChIKey

ANEDZEVDORCLPM-UHFFFAOYSA-N

SMILES

S1CCCSC1C(OCC)=O

CAS DataBase Reference

20462-00-4(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 1,3-dithiane-2-carboxylate(20462-00-4)

Safety Information

Risk Statements 

10

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

F 

9-13

HazardClass 

3

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:2-Carboethoxy-1,3-dithiane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 1,3-dithiane-2-carboxylate Usage And Synthesis

Chemical Properties

clear yellowish liquid

Uses

Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.

Preparation

To a solution of BF3. Et2O (57.5 mL, 0.454 mmol) in CHC13 (180 mL) heated at reflux was added dropwise, over a 1h period, a solution of 1,3-propanedithiol (22.7 mL, 0.227 mmol), followed by ethyl diethoxyacetate (40 g, 0.227 mmol) in CHCl3 (40 mL). The resulting mixture was heated for 30 minutes, and then cooled to rt. The cooled solution was washed 2 times with water, once with saturated aqueous NaHC03, and then re-washed with water. The combined organic phases were dried over MgS04, then evaporated to give 41 g (94%) of Ethyl 1,3-dithiane-2-carboxylate as a yellow oi. Yield: 94%

Application

Ethyl 1,3-dithiane-2-carboxylate is a synthetic compound that is used in the synthesis of organic compounds . It is used in asymmetric synthesis to produce chiral products from achiral starting materials. The desulfurization reaction of ethyl 1,3-dithiane-2-carboxylate produces a mixture of the two possible stereoisomers of the product. This mixture can be separated by phase chromatography and then hydrolyzed to give the desired product. In dyslipidemia, ethyl 1,3-dithiane-2-carboxylate inhibits the activity of hepatic lipase and acidolysis. This inhibition leads to an increase in serum triglycerides and cholesterol levels. This compound also has been shown to have antiplatelet properties when administered orally or intravenously to rats without affecting platelet aggregation rates.

Synthesis Reference(s)

Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615

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.

Purification Methods

Dissolve the ester in CHCl3, wash with aqueous K2CO3, twice with H2O, dry over MgSO4, filter, evaporate and distil the residue. [Eliel & Hartman J Org Chem 37 505 1972, Seebach Synthesis 1 17 1969, Beilstein 19/7 V 227.]

Ethyl 1,3-dithiane-2-carboxylate(20462-00-4)Related Product Information

• 1,3-Dithiane
• ISOXADIFEN-ETHYL
• Ethanol
• Urethane
• Ethyl acetate
• Ethyl cyanoacetate
• Benzocaine
• Ethyl formate
• Ethyl acrylate
• Ethyl pyruvate
• RESMETHRIN
• Ethyl cyanoformate
• Ethylparaben
• Ethyl chloroformate
• Methyl thioglycolate
• METHYL (METHYLTHIO)ACETATE
• 2-METHYL-1,3-DITHIANE
• 1,3-DITHIANE-2-CARBOXYLIC ACID