methyl (2R)-3-hydroxy-2-methylpropanoate

• ChemBase ID: 149567
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: C[C@H](CO)C(=O)OC
• Canonical SMILES: C[C@@H](C(=O)OC)CO
• InChI: InChI=1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
• InChIKey: ATCCIZURPPEVIZ-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-3-hydroxy-2-methylpropanoate
• IUPAC Traditional name: methyl (2R)-3-hydroxy-2-methylpropanoate
• Synonyms: (-)-Methyl D-β-hydroxyisobutyrate; (R)-(-)-3-Hydroxy-2-methylpropionic acid methyl ester; Methyl (R)-(-)-3-hydroxy-2-methylpropionate; Methyl (R)-3-hydroxy-2-methylpropionate; (-)-Methyl D-β-hydroxyisobutyrate; (R)-Methyl 3-hydroxy-2-methylpropanoate; (-)-Methyl β-Hydroxyisobutyrate; (2R)-3-Hydroxy-2-methylpropionic Acid Methyl Ester; Methyl (R)-(-)-3-Hydroxy-2-methylpropionate; R-(-)-Roche Ester; (R)-3-Hydroxyisobutyric Acid Methyl Ester; (-)-甲基D-β-羟基异丁酸酯; (R)-(-)-3-羟基-2-异丁酸甲酯; (R)-(-)-3-羟基-2-甲基丙酸甲酯; (R)-(-)-3-羟基-2-甲基丙酸甲酯; (R)-3-羟基-2-甲基丙酸甲酯; (-)-甲基D-β-羟基异丁酸酯

Database IDs

• CAS Number: 72657-23-9
• MDL Number: MFCD00063450
• Beilstein Number: 3587507
• PubChem SID: 24879379; 24856357; 162243732
• PubChem CID: 5324733

CALCULATED PROPERTIES

• Acid pKa: 15.242007
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.11470069
• LogD (pH = 7.4): -0.1147007
• Log P: -0.11470069
• Molar Refractivity: 28.3889 cm^3
• Polarizability: 11.390625 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Clear Colorless Oil
• Boiling Point: 76-77 °C/12 mmHg(lit.)
• Flash Point: 176 °F; 80 °C
• Density: 1.066 g/mL at 20 °C(lit.); 1.066 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.425; n20/D 1.425(lit.)
• Optical Rotation: [α]19/D -26°, c = 4 in methanol; [α]20/D -26±1°, c = 2% in methanol

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Risk Statements: 10
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95+%; 99%
• Grade: purum
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99.0:1.0
• Linear Formula: HOCH2CH(CH3)CO2CH3
• Empirical Formula (Hill Notation): C5H10O3

DETAILS

Sigma Aldrich - 270148

Packaging
1, 5 g in glass bottle
Application
The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.1,2,3

Toronto Research Chemicals - H943558

Chiral derivative of 3-Hydroxyisobutyrate.

REFERENCES

• Waldmann, H., et al.: Bioorg. Med. Chem., 2, 477 (1994)
• Vonstein, V., et al.: J. Bacteriol., 177, 4540 (1994)