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

• ChemBase ID: 145805
• Molecular Formular: C6H10O6
• Molecular Mass: 178.14
• Monoisotopic Mass: 178.04773804
• SMILES: COC(=O)[C@@H]([C@H](C(=O)OC)O)O
• Canonical SMILES: COC(=O)[C@@H]([C@H](C(=O)OC)O)O
• InChI: InChI=1S/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m1/s1
• InChIKey: PVRATXCXJDHJJN-QWWZWVQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl (2R,3R)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: 1,4-dimethyl (2R,3R)-2,3-dihydroxybutanedioate
• Synonyms: L-(+)-Tartaric acid dimethyl ester; (+)-Dimethyl L-tartrate; D-Tartaric acid dimethyl ester; Dimethyl D-tartrate; (2R,3R)-Dimethyl 2,3-dihydroxysuccinate; L-(+)-酒石酸二甲酯; D-(-)酒石酸二甲酯

Database IDs

• CAS Number: 13171-64-7; 608-68-4
• EC Number: 210-166-8; 236-118-6
• MDL Number: MFCD00008445; MFCD00064437
• Beilstein Number: 1726254; 1726256
• PubChem SID: 24890143; 24849749; 162240007
• PubChem CID: 11851

CALCULATED PROPERTIES

• Acid pKa: 11.18821
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.5370127
• LogD (pH = 7.4): -1.5370824
• Log P: -1.5370117
• Molar Refractivity: 35.7516 cm^3
• Polarizability: 14.854973 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~58 °C; 48-56°C; 57-60 °C (dec.)(lit.)
• Boiling Point: 158°C/11mm; 163 °C/23 mmHg(lit.)
• Flash Point: >113 °C; >170°C(338°F); >235.4 °F
• Density: 1.238 g/mL at 25 °C(lit.); 1.30
• Optical Rotation: [α]20/D +21±1°, c = 1% in H2O; [α]22/D +21°, c = 2.5 in H2O; -21 (c=1 in water)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95+%; 99%
• Grade: purum
• Optical Purity: ee: ≥99% (GLC)
• Linear Formula: [-CH(OH)CO2CH3]2

DETAILS

Sigma Aldrich - 163457

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 95365

Other Notes
Chiral auxiliary used for the enantioselective epoxidation of allylic alcohols, Sharpless AE 1,2; Asymmetric α-halogenation of acetals 3; Starting material for the synthesis of chiral building blocks 4