270148

Methyl (R)-(−)-3-hydroxy-2-methylpropionate

99%

• Synonym(s): (−)-Methyl D-β-hydroxyisobutyrate, (R)-(−)-3-Hydroxy-2-methylpropionic acid methyl ester
• Linear Formula: HOCH₂CH(CH₃)CO₂CH₃
• CAS Number: 72657-23-9
• Molecular Weight: 118.13
• Beilstein/REAXYS Number: 3587507
• MDL number: MFCD00063450
• UNSPSC Code: 12352108
• PubChem Substance ID: 24856357
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 99%
• form: liquid
• optical activity: [α]19/D −26°, c = 4 in methanol
• optical purity: ee: 99% (GLC)
• refractive index: n20/D 1.425 (lit.)
• bp: 76-77 °C/12 mmHg (lit.)
• density: 1.066 g/mL at 25 °C (lit.)
• functional group: ester; hydroxyl
• SMILES string: COC(=O)[C@H](C)CO
• InChI: 1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
• InChI key: ATCCIZURPPEVIZ-SCSAIBSYSA-N

Description

Application

Methyl (R)-(-)-3-hydroxy-2-methylpropionate may be used in the preparation of (S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane.[1] It may also be used as a starting material in the total synthesis of (-)-discodermolide[2], (-)-stemoamide[3] and (-)-stemospironine.[4]

The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.[5][6][7]

Safety Information

• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 176.0 °F - closed cup
• flash_point_c: 80 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter