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Sigma-Aldrich

(S)-(−)-1,2,4-Butanetriol

98%

Synonym(s):

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

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About This Item

Linear Formula:
HOCH2CH2CH(OH)CH2OH
CAS Number:
42890-76-6
Molecular Weight:
106.12
Beilstein:
1719408
MDL number:
MFCD00063213
UNSPSC Code:
12352001
PubChem Substance ID:
24857865
NACRES:
NA.22

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.)

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

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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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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An efficient asymmetric synthesis of 2-substituted ferrocenecarboxaldehydes
Riant O, et al
The Journal of Organic Chemistry, 62(20), 6733-6745 (1997)
Asymmetric Michael addition of thiophenol to maleic acid esters
Yamashita H and Mukaiyama T
Chemistry Letters (Jpn), 14(3), 363-366 (1985)
Enantioselective total synthesis of (+)-azimine and (+)-carpaine.
Sato T, et al.
Organic Letters, 5(21), 3839-3842 (2003)
Facile access to (S)-1, 2, 4-butanetriol and its derivatives.
Hanessian S, et al.
Canadian Journal of Chemistry, 62(11), 2146-2147 (1984)

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