43798

Ethyl 1,3-dithiolane-2-carboxylate

≥98.0%

• Synonym(s): Glyoxylic acid ethyl ester ethylene mercaptal
• Empirical Formula (Hill Notation): C₆H₁₀O₂S₂
• CAS Number: 20461-99-8
• Molecular Weight: 178.27
• Beilstein: 118157
• EC Number: 243-837-9
• MDL number: MFCD00005411
• UNSPSC Code: 12352100
• PubChem Substance ID: 24867412

Properties

• Assay: ≥98.0%
• refractive index: n20/D 1.539 (lit.); n20/D 1.540
• bp: 85 °C/0.1 mmHg (lit.)
• density: 1.249 g/mL at 25 °C (lit.)
• SMILES string: CCOC(=O)C1SCCS1
• InChI: 1S/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3
• InChI key: OMCSHTHLIQOHDD-UHFFFAOYSA-N

Description

General description

Ethyl 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.

Other Notes

α-Keto acid equivalent; conjugate additions to enones ; bulky equivalent of acetate undergoing syn-selective aldol reactions

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves