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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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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)
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)
X Cheng et al.
Drug metabolism and disposition: the biological fate of chemicals, 21(1), 121-124 (1993-01-01)
A rapid, simple extraction and GC assay procedure is described that allows quantitation of micromolar concentrations of butadiene bisoxide and 3-butene-1,2-diol in microsomal suspensions exposed to butadiene. Butane-1,4-diol is used as the internal standard. The recovery of these compounds from
R J Krause et al.
Chemical research in toxicology, 14(12), 1590-1595 (2001-12-18)
The metabolic fate of 3-butene-1,2-diol (BDD), a secondary metabolite of the industrial carcinogen, 1,3-butadiene, is unclear. The current study characterizes BDD oxidation to hydroxymethylvinyl ketone (HMVK), a reactive Michael acceptor. Because of its instability in aqueous medium, HMVK was trapped
Gregory M Sandala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(19), 4865-4873 (2009-03-28)
High-level conventional ab initio and density functional theory (DFT) calculations have been performed to examine the fate of the native substrate glycerol (1) and its analogue but-3-ene-1,2-diol (7) in the coenzyme B(12)-dependent enzyme glycerol dehydratase (GDH). Experimental studies find that
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