296678

(S)-(−)-1,2,4-Butanetriol

98%

• Synonym(s): (2S)-(-)-Butane-1,2,4-triol, (S)-(-)-1,2,4-Trihydroxybutane
• Linear Formula: HOCH₂CH₂CH(OH)CH₂OH
• CAS Number: 42890-76-6
• Molecular Weight: 106.12
• Beilstein/REAXYS Number: 1719408
• MDL number: MFCD00063213
• UNSPSC Code: 12352001
• PubChem Substance ID: 24857865
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 98%
• optical activity: [α]19/D −28±2, c = 1 in methanol
• optical purity: ee: 99% (GLC)
• refractive index: n20/D 1.475 (lit.)
• bp: 150 °C/0.04 mmHg (lit.)
• density: 1.19 g/mL at 25 °C (lit.)
• functional group: hydroxyl
• SMILES string: OCC[C@H](O)CO
• InChI: 1S/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2/t4-/m0/s1
• InChI key: ARXKVVRQIIOZGF-BYPYZUCNSA-N

Description

General description

(S)-(-)-1,2,4-Butanetriol can be prepared via reduction of (S)-malic acid in the presence of borane-dimethyl sulfide.[1]

Application

(S)-(-)-1,2,4-Butanetriol may be used as a starting material in the enantioselective total syntheses of (+)-azimine and (+)-carpaine.[2]
It can also be used to prepare the following organic building blocks:

• (+)-3,4-epoxy-1-butanol[3]
• (2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxane[4]
• (S)-1,2,4-triacetoxybutane via acetylation with acetic anhydride[1]
• (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane via esterification with 3,5-dinitrobenzoyl chloride[1]

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)