1,4-diethyl (2S,3S)-2,3-dihydroxybutanedioate

• ChemBase ID: 127008
• Molecular Formular: C8H14O6
• Molecular Mass: 206.19316
• Monoisotopic Mass: 206.07903817
• SMILES: O=C(OCC)[C@@H](O)[C@H](O)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H]([C@@H](C(=O)OCC)O)O
• InChI: InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1
• InChIKey: YSAVZVORKRDODB-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-diethyl (2S,3S)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: diethyl tartrate
• Synonyms: Diethyl tartrate; D-(-)-Tartaric acid diethyl ester; (-)-Diethyl D-tartrate; L-Tartaric acid diethyl ester; (+)-Diethyl L-tartrate; D-Tartaric acid diethyl ester; (2S,3S)-Diethyl 2,3-dihydroxysuccinate; D-(-)-酒石酸二乙酯; L-(+)-酒石酸二乙酯

Database IDs

• CAS Number: 13811-71-7; 87-91-2
• EC Number: 201-783-3; 237-458-8
• MDL Number: MFCD00009143; MFCD00064451
• Beilstein Number: 1727145; 1727143
• Merck Index: 143855
• PubChem SID: 162221331; 24852814
• PubChem CID: 117410; 62333
• Chemspider ID: 104927
• Wikipedia Title: Diethyl_tartrate

CALCULATED PROPERTIES

• Acid pKa: 11.187077
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.82339674
• LogD (pH = 7.4): -0.8234667
• Log P: -0.82339585
• Molar Refractivity: 45.2488 cm^3
• Polarizability: 18.454937 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: low in water
• Apperance: colourless
• Melting Point: 17°C
• Boiling Point: 162 °C/19 mmHg(lit.); 280 °C; 280°C
• Flash Point: 199.4 °F; 93 °C; 93°C(199°F)
• Density: 1.204 g/mL; 1.205; 1.205 g/mL at 20 °C(lit.)
• Refractive Index: 1.4460; n20/D 1.446(lit.); n20/D 1.447
• Optical Rotation: [α]20/D -26.5±1°, c = 1% in H2O; [α]23/D -8.5°, neat; +27 (c=1 in water); -26.5 (c=1 in water)

Safety Information

• German water hazard class: 3
• Safety Statements: 15
• TSCA Listed: 否; 是
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, GC); 98%; 99%
• Grade: puriss.
• Optical Purity: ee: ≥99% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: HO2CCCH(OH)CH(OH)CO2H

DETAILS

Sigma Aldrich - 213969

Packaging
5, 25, 500 g in glass bottle

REFERENCES

• For use as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl hydroperoxide, A13926. For Sharpless-type enantioselective oxidation of sulfides to sulfoxides, see: Org. Synth. Coll., 8, 464 (1993).
• For use as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction, see: Chem. Lett., 61 (1992). For a review of the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).