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488216

Sigma-Aldrich

3,4-Dihydroxy-1-butene

≥99%

Sinónimos:

3-Butene-1,2-diol

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About This Item

Fórmula lineal:
CH2=CHCH(OH)CH2OH
Número de CAS:
497-06-3
Peso molecular:
88.11
Beilstein/REAXYS Number:
1633578
EC Number:
207-835-1
MDL number:
MFCD00239410
UNSPSC Code:
12352100
PubChem Substance ID:
24872379
NACRES:
NA.22

assay

≥99%

bp

195 °C/733 mmHg (lit.)

density

1.047 g/mL at 25 °C (lit.)

SMILES string

OCC(O)C=C

InChI

1S/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2

InChI key

ITMIAZBRRZANGB-UHFFFAOYSA-N

Categorías relacionadas

General description

3,4-Dihydroxy-1-butene, also known as 3-butene-1,2-diol (BDdiol), is a metabolite of 1,3-butadiene. It forms the precursor for synthesizing different chiral building blocks. BDdiol can undergo oxidation to form hydroxymethylvinyl ketone (HMVK). 1,2-epoxy-3-butene (EB) on hydrolysis in the presence of epoxide hydrolases (EH) forms BDdiol.

Application

3,4-Dihydroxy-1-butene can be used:
  • As a reactant to synthesize cyclic organic carbonates by continuous flow procedure.
  • To prepare substituted oxazolidinone ligands used to target medicinally relevant RNAs.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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Sigma-Aldrich

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Versatile and scalable synthesis of cyclic organic carbonates under organocatalytic continuous flow conditions
Gerardy R, et al.
Catalysis Science & Technology, 9(24), 6841-6851 (2019)
3-Butene-1, 2-diol: An attractive precursor for the synthesis of enantiomerically pure organic compounds.
Rao AVR, et al.
Tetrahedron, 45(22), 7031-7040 (1989)
Christopher L Sprague et al.
Chemical research in toxicology, 17(6), 819-826 (2004-06-23)
3-Butene-1,2-diol (BDD), a major metabolite of 1,3-butadiene (BD), can readily be oxidized to hydroxymethylvinyl ketone (HMVK), a Michael acceptor. In previous studies, 4-(N-acetyl-l-cystein-S-yl)-1,2-dihydroxybutane (DHB), a urinary metabolite of BD that was used to assess human BD exposure, was suggested to
Crina M Orac et al.
Journal of medicinal chemistry, 54(19), 6786-6795 (2011-08-05)
The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that
Céline Brochot et al.
Chemico-biological interactions, 167(3), 168-183 (2007-04-03)
1,3-Butadiene (BD) is metabolized in humans and rodents to mutagenic and carcinogenic species. Our previous work has focused on developing a physiologically based toxicokinetic (PBTK) model for BD to estimate its metabolic rate to 1,2-epoxy-3-butene (EB), using exhaled breath BD
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