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488216

Sigma-Aldrich

3,4-Dihydroxy-1-butene

≥99%

Synonym(s):

3-Butene-1,2-diol

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25 ML
$267.26
100 ML
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About This Item

Linear Formula:
CH2=CHCH(OH)CH2OH
CAS Number:
497-06-3
Molecular Weight:
88.11
Beilstein/REAXYS Number:
1633578
EC Number:
207-835-1
MDL number:
MFCD00239410
UNSPSC Code:
12352100
PubChem Substance ID:
24872379
NACRES:
NA.22

$267.26

List Price$288.00Save 7%
Web-Only Promotion

Available to ship onApril 22, 2025Details

Request a Bulk Order

Quality Level

100

assay

≥99%

bp

195 °C/733 mmHg (lit.)

density

1.047 g/mL at 25 °C (lit.)

functional group

hydroxyl

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

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General description

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

Application

3,4-Dihydroxy-1-butene can be used:
  • As a reactant to synthesize cyclic organic carbonates by continuous flow procedure.[5]
  • To prepare substituted oxazolidinone ligands used to target medicinally relevant RNAs.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
00228KS

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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)
R A Kemper et al.
Drug metabolism and disposition: the biological fate of chemicals, 26(9), 914-920 (1998-09-12)
3-Butene-1,2-diol (BDD), a metabolite of 1,3-butadiene, is rapidly metabolized by B6C3F1 mice at doses ranging from 10 to 250 mg/kg. Calculation of plasma clearance suggested that the kinetics of BDD metabolism were dose-dependent. Clearance varied 5-fold in this dose range.
J G Filser et al.
Chemico-biological interactions, 135-136, 249-265 (2001-06-09)
First-pass metabolism of 1,3-butadiene (BD) leading to 1,2-epoxy-3-butene (EB), 1,2:3,4-diepoxybutane (DEB), 3-butene-1,2-diol (B-diol), 3,4-epoxy-1,2-butanediol (EBD) and crotonaldehyde (CA) was studied quantitatively in the once-through BD perfused liver of mouse and rat by means of an all-glass gas-tight perfusion system. Metabolites
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
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