ethyl 1,3-dithiane-2-carboxylate

• ChemBase ID: 138963
• Molecular Formular: C7H12O2S2
• Molecular Mass: 192.29898
• Monoisotopic Mass: 192.02787162
• SMILES: CCOC(=O)C1SCCCS1
• Canonical SMILES: CCOC(=O)C1SCCCS1
• InChI: InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
• InChIKey: ANEDZEVDORCLPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1,3-dithiane-2-carboxylate
• IUPAC Traditional name: ethyl 1,3-dithiane-2-carboxylate
• Synonyms: Glyoxylic acid ethyl ester trimethylenemercaptal; Ethyl 1,3-dithiane-2-carboxylate; 2-Carboethoxy-1,3-dithiane; 1,3-Dithiane-2-carboxylic acid ethyl ester; 乙醛酸乙酯三亚甲基缩硫醛; 1,3-二噻烷-2-甲酸乙酯

Database IDs

• CAS Number: 20462-00-4
• EC Number: 243-838-4
• MDL Number: MFCD00006657
• Beilstein Number: 1424352
• PubChem SID: 162233214; 24867377
• PubChem CID: 88552

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7158928
• LogD (pH = 7.4): 1.7158928
• Log P: 1.7158928
• Molar Refractivity: 49.6128 cm^3
• Polarizability: 19.815737 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 19-21°C
• Boiling Point: 75-77 °C/0.2 mmHg(lit.); 75-77°C/0.2mm
• Flash Point: 131 °F; 54°C(129°F); 55 °C
• Density: 1.22 g/mL at 25 °C(lit.); 1.220
• Refractive Index: 1.5400; n20/D 1.539(lit.); n20/D 1.541

Safety Information

• UN Number: 3272; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3

Product Information

• Purity: ≥90% (GC); 97%; 98+%
• Grade: technical
• Empirical Formula (Hill Notation): C7H12O2S2

DETAILS

Sigma Aldrich - 235415

Application
Reagent for the synthesis of α-ketoesters.

Sigma Aldrich - 43749

Other Notes
α-Keto acid equivalent1,2,3; bulky equivalent of acetate undergoing syn-selective aldol reactions4
Packaging
5 mL in glass bottle

REFERENCES

• Alkylation of the anion provides a route to ɑ-keto acids (by dethioketalization with NBS), or to substituted acetic acids (by desulfurization): J. Org. Chem., 37, 505 (1972). For phase-transfer alkylation using allylic bromides, see: Liebigs Ann. Chem., 1589 (1982). With crotyl bromide, approx. 95% allylic rearrangement occurs.
• The lithiated derivative undergoes 1,4- (Michael) addition to a variety of ɑ?-unsaturated compounds. However, the Mg derivative prepared by metallation with an alkylmagnesium halide gives an allylic alcohol by 1,2-addition: Chem. Ber., 114, 2924 (1981).