ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE

ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Basic information
Product Name:ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE
Synonyms:ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE;ETHYL GLYOXYLATE ETHYLENE THIOACETAL;GLYOXYLIC ACID ETHYL ESTER ETHYLENE MERCAPTAL;2-Carboethoxy-1,3-dithiolane~1,3-Dithiolane-2-carboxylicacidethylester~2-Ethoxycarbonyl-1,3-dithiolane~Ethylglyoxyla;1,3-DITHIOLANE-2-CARBOXYLIC ACID ETHYL ESTER;2-Carboethoxy-1,3-dithiolane;2-Carboethoxydithiolane;Ethyl 1,3-dithiolane-2-carboxylate, GC 99%
CAS:20461-99-8
MF:C6H10O2S2
MW:178.27
EINECS:243-837-9
Product Categories:Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Heterocyclic Compounds
Mol File:20461-99-8.mol
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Structure
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Chemical Properties
Boiling point 85 °C/0.1 mmHg (lit.)
density 1.249 g/mL at 25 °C (lit.)
refractive index n20/D 1.539(lit.)
Fp >230 °F
storage temp. 2-8°C
form Liquid
color Clear light yellow
Specific Gravity1.249
BRN 118157
CAS DataBase Reference20461-99-8(CAS DataBase Reference)
Safety Information
Safety Statements 23-24/25
RIDADR 3334
WGK Germany 3
8-9
HS Code 29349990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Usage And Synthesis
Chemical Propertiesclear light yellow liquid
General DescriptionEthyl 1,3-dithiolane-2-carboxylate is an α-keto acid equivalent. It participates in the conjugate additions to enones. It is a bulky equivalent of acetate undergoing syn-selective aldol reactions. Anion derived from ethyl 1,3-dithiolane-2-carboxylate participates as nucleophile during the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline and hirsutine. It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams.
Purification MethodsDissolve the ester in CHCl3, wash it with aqueous K2CO3, twice with H2O, dry it over MgSO4, filter, evaporate and distil the residue in vacuo. [Hermann et al Tetrahedron Lett 2599 1973, Corey & Erickson J Org Chem 36 3553 1971]. [Beilstein 19/7 V 225.]
ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Preparation Products And Raw materials
Raw materialsEthanol-->Potassium-->1,2-Ethanedithiol-->ETHYL DIBROMOACETATE
Preparation Products1,3-dithiolan-2-ylmethanol
Methyl thioglycolate Bis(methylthio)methane ETHYL THIOGLYCOLATE 1,3-DITHIOLANE ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE METHYL (METHYLTHIO)ACETATE (ETHYLTHIO)ACETIC ACID ETHYL (METHYLTHIO)ACETATE 1,2-Ethanedithiol Ethyl 2-hydroxyethyl sulfide 1-(methylthio)ethanethiol (METHYLTHIO)ACETIC ACID Mercaptoacetic acid 2-METHYL-1,3-DITHIOLANE 2-methoxyethanethiol

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