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.[1][2] It is a bulky equivalent of acetate undergoing syn-selective aldol reactions.[3] 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.[4] It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams.[5]

Other Notes

α-Keto acid equivalent; conjugate additions to enones [1][2]; bulky equivalent of acetate undergoing syn-selective aldol reactions[3]

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