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

• ChemBase ID: 145800
• Molecular Formular: C8H14O6
• Molecular Mass: 206.19316
• Monoisotopic Mass: 206.07903817
• SMILES: CCOC(=O)[C@@H]([C@H](C(=O)OCC)O)O
• 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-/m1/s1
• InChIKey: YSAVZVORKRDODB-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 87-91-2
• EC Number: 201-783-3
• MDL Number: MFCD00009143
• Beilstein Number: 1727145
• PubChem SID: 24849640; 24890139; 24901033; 162240002
• PubChem CID: 6993580
• FEMA ID: 2378
• Council of Europe Number: 440
• Flavis Number: 9.446

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

• Boiling Point: 280 °C(lit.)
• Flash Point: 199.4 °F; 93 °C
• Density: 1.204 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.446(lit.); n20/D 1.447
• Optical Rotation: [α]20/D +26.5±1°, c = 1% in H2O; [α]20/D +8.5°, neat
• Organoleptic: fruity; wine-like

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: FDA 21 CFR (172.515)

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, GC)
• Grade: Kosher; NI; puriss.
• Optical Purity: ee: ≥99% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: [-CH(OH)CO2C2H5]2

DETAILS

Sigma Aldrich - 156841

General description
Made from natural tartaric acid
Packaging
25, 100, 500 g in glass bottle

Sigma Aldrich - W237809

Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in poly drum

Sigma Aldrich - 95355

Other Notes
Chiral catalyst for the enantioselective epoxidation of allylic alcohols, Sharpless AE 1; Chiral auxiliary, e.g. for preparing chiral ortho esters, or chiral allylboronates 2,3,4; Synthesis of chiral building blocks 5