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

• ChemBase ID: 74448
• Molecular Formular: C10H18O6
• Molecular Mass: 234.24632
• Monoisotopic Mass: 234.1103383
• SMILES: C(C)(C)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(C)C
• Canonical SMILES: O[C@@H]([C@@H](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/t7-,8-/m0/s1
• InChIKey: XEBCWEDRGPSHQH-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis(propan-2-yl) (2S,3S)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: 1,4-diisopropyl (2S,3S)-2,3-dihydroxybutanedioate
• Synonyms: Dipropan-2-yl 2,3-dihydroxybutanedioatd; DIPT; Diisopropyl tartrate; Bis(1-methylethyl) ester of 2,3-dihydroxybutanedioic acid; D-(-)-Tartaric acid diisopropyl ester; (-)-Diisopropyl D-tartrate; D-(-)-Tartaric acid diisopropyl ester; (2S,3S)-Diisopropyl 2,3-dihydroxysuccinate; 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: MFCD00008876
• Beilstein Number: 5265431
• PubChem SID: 24890144; 24853655; 162039367
• PubChem CID: 102768; 112972
• Chemspider ID: 101254
• Wikipedia Title: Diisopropyl_tartrate

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: 152 °C (425.2 K) at 16 kPa
• Flash Point: 110 °C; 230 °F
• Density: 1.10 g/ml; 1.119 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.439(lit.); n20/D 1.440
• Optical Rotation: [α]20/D -16±1°, neat; [α]23/D -17°, neat

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 98%
• Grade: purum
• Optical Purity: ee: ≥99% (GLC)
• Linear Formula: [-CH(OH)CO2CH(CH3)2]2

DETAILS

MP Biomedicals - 02156742

([-]-Diisopropyl D-tartrate)
1 ml = approx. 1.10 g

Sigma Aldrich - 227803

Packaging
10, 50 g in glass bottle
Application
Both D- and L-forms are reagents for kinetic resolution of racemic allylic alcohols1,2,3 and α-furfuryl amides4 by enantioselective epoxidation.