43749

Ethyl 1,3-dithiane-2-carboxylate

technical, ≥90% (GC)

• Synonym(s): Glyoxylic acid ethyl ester trimethylenemercaptal
• Empirical Formula (Hill Notation): C₇H₁₂O₂S₂
• CAS Number: 20462-00-4
• Molecular Weight: 192.30
• Beilstein: 1424352
• EC Number: 243-838-4
• MDL number: MFCD00006657
• UNSPSC Code: 12352100
• PubChem Substance ID: 24867377
• NACRES: NA.22

Properties

• grade: technical
• Assay: ≥90% (GC)
• refractive index: n20/D 1.539 (lit.); n20/D 1.541
• bp: 75-77 °C/0.2 mmHg (lit.)
• density: 1.22 g/mL at 25 °C (lit.)
• SMILES string: CCOC(=O)C1SCCCS1
• InChI: 1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
• InChI key: ANEDZEVDORCLPM-UHFFFAOYSA-N

Description

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.

Safety Information

• Pictograms: GHS02
• Signal Word: Warning
• Hazard Statements: H226
• Hazard Classifications: Flam. Liq. 3
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 131.0 °F - closed cup
• Flash Point(C): 55 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves