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296678 Sigma-Aldrich

(S)-(−)-1,2,4-Butanetriol

98%

Synonym: (2S)-(-)-Butane-1,2,4-triol, (S)-(-)-1,2,4-Trihydroxybutane

  • CAS Number 42890-76-6

  • Linear Formula HOCH2CH2CH(OH)CH2OH

  • Molecular Weight 106.12

  •  Beilstein/REAXYS Number 1719408

  •  MDL number MFCD00063213

  •  PubChem Substance ID 24857865

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Organic Building Blocks, Polyols More...
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.)
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.

Application

(S)-(-)-1,2,4-Butanetriol may be used as a starting material in the enantioselective total syntheses of (+)-azimine and (+)-carpaine.
It can also be used to prepare the following organic building blocks:
• (+)-3,4-epoxy-1-butanol
• (2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxane
• (S)-1,2,4-triacetoxybutane via acetylation with acetic anhydride
• (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane via esterification with 3,5-dinitrobenzoyl chloride

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
110 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

ASTM D6584: GC Analysis of Glycerin Impurity in B100 Biodiesel on MET-Biodiesel

From our library of Articles, Sigma-Aldrich presents ASTM D6584: GC Analysis of Glycerin Impurity in B100 Biodiesel on MET-Biodiesel
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

Peer-Reviewed Papers
15

References

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