1,4-bis(propan-2-yl) 2,3-dihydroxybutanedioate

• ChemBase ID: 295426
• Molecular Formular: C10H18O6
• Molecular Mass: 234.24632
• Monoisotopic Mass: 234.1103383
• SMILES: CC(C)OC(=O)C(C(C(=O)OC(C)C)O)O
• Canonical SMILES: OC(C(C(=O)OC(C)C)O)C(=O)OC(C)C
• InChI: InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3
• InChIKey: XEBCWEDRGPSHQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis(propan-2-yl) 2,3-dihydroxybutanedioate
• IUPAC Traditional name: diisopropyl tartrate
• Synonyms: L-Tartaric acid diisopropyl ester; (+)-Diisopropyl L-tartrate; D-Tartaric acid diisopropyl ester; (-)-Diisopropyl D-tartrate; L-(+)-酒石酸二异丙酯; D-(-)-酒石酸二异丙酯

Database IDs

• CAS Number: 62961-64-2; 2217-15-4
• EC Number: 218-709-0; 263-771-4
• MDL Number: MFCD00064450; MFCD00008876
• Beilstein Number: 1727863; 5265431
• PubChem SID: 180680957
• PubChem CID: 102768

CALCULATED PROPERTIES

• Acid pKa: 11.185941
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.009753288
• LogD (pH = 7.4): 0.009683163
• Log P: 0.009754182
• Molar Refractivity: 54.0864 cm^3
• Polarizability: 22.078806 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 150-151°C/11mm
• Flash Point: 110°C(230°F)
• Density: 1.117
• Refractive Index: 1.4400
• Optical Rotation: +16 (neat); -16 (neat)

Safety Information

• RTECS: WW8100000
• TSCA Listed: 否; 是

Product Information

• Purity: 98%; 98+%

REFERENCES

• For the use of esters of tartaric acid as chiral auxiliaries in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl hydroperoxide, A13926. For a review the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith cyclopropanantion reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).
• Chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols; see tert-Butyl hydroperoxide, A13926.