Ethyl 1,3-dithiane-2-carboxylate

Ethyl 1,3-dithiane-2-carboxylate
  • CAS No.:20462-00-4

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Ethyl 1,3-dithiane-2-carboxylate Basic information
Product Name:Ethyl 1,3-dithiane-2-carboxylate
Synonyms:ETHYL-1 3-DITHIANE-2-CARBOXYLATE 99% (&;Ethyl 1,3-dithiane-2-carboxylate, 98+%;2-Ethoxycarbonyl-1,3-dithiane;Ethyl Glyoxylate Trimethylene Dithioacetal;ETHYL 1,3-DITHIANE-2-CARBOXYLATE FOR SYN;m-Dithiane-2-carboxylic acid, ethyl ester;2-Carboethoxy-1,3-dithiane;Carboethoxy-1,3-dithiane
CAS:20462-00-4
MF:C7H12O2S2
MW:192.3
EINECS:243-838-4
Product Categories:Heterocyclic Compounds;Sulfur Compounds (for Synthesis);Sulfur compounds;Synthetic Organic Chemistry
Mol File:20462-00-4.mol
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.)
Fp 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
InChIKeyANEDZEVDORCLPM-UHFFFAOYSA-N
CAS DataBase Reference20462-00-4(CAS DataBase Reference)
NIST Chemistry ReferenceEthyl 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 Information
ProviderLanguage
2-Carboethoxy-1,3-dithiane English
ACROS English
SigmaAldrich English
ALFA English
Ethyl 1,3-dithiane-2-carboxylate Usage And Synthesis
Chemical Propertiesclear yellowish liquid
UsesEthyl 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.
Synthesis Reference(s)Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615
General DescriptionEthyl 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 MethodsDissolve 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 Preparation Products And Raw materials
Raw materialsAcetic acid, 2,2-dihydroxy-, ethyl ester-->Ethyl trichloroacetate-->Ethyl diethoxyacetate-->1,3-Dimercaptopropane-->ETHYL DICHLOROACETATE

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