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Merck
CN

38715

Sigma-Aldrich

(S,S)-(−)-1,4-Dimethoxy-2,3-butanediol

≥99.0% (sum of enantiomers, GC)

Synonym(s):

(−)-1,4-Di-O-methyl-L-threitol

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About This Item

Empirical Formula (Hill Notation):
C6H14O4
CAS Number:
Molecular Weight:
150.17
Beilstein:
2322227
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
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Assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D −1.8±0.1°, c = 1.9% in methanol

mp

28-30 °C

storage temp.

2-8°C

SMILES string

COC[C@H](O)[C@@H](O)COC

InChI

1S/C6H14O4/c1-9-3-5(7)6(8)4-10-2/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1

InChI key

QPXJVYUZWDGUBO-WDSKDSINSA-N

Other Notes

Chiral auxiliary, modification of LAH; Condensation of ester enolates and chiral imines to β-lactams; Auxiliary, reactions of its acetal, review; Determination of the enantiomeric purity of ketones by acetal formation and 13C-NMR.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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T. Fujisawa et al.
Tetrahedron, 48, 5629-5629 (1992)
M. Schmidt et al.
Chemische Berichte, 113, 1691-1691 (1980)
W. Langer et al.
Helvetica Chimica Acta, 62, 1710-1710 (1978)
A. Alexakis et al.
Tetrahedron Asymmetry, 1, 477-477 (1990)

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