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/REAXYS Number: 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.)
• functional group: ester; thioether
• 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[1][2][3] and bulky equivalent of acetate. It participates in syn-selective aldol reactions.[4] It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF₃/Et₂O.[3] Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield.[5] Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.[6]

Safety Information

• pictograms: GHS02
• signalword: Warning
• hcodes: H226
• Hazard Classifications: Flam. Liq. 3
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 131.0 °F - closed cup
• flash_point_c: 55 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter