Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

488216

Sigma-Aldrich

3,4-Dihydroxy-1-butene

≥99%

Synonym(s):

3-Butene-1,2-diol

Sign Into View Organizational & Contract Pricing

Select a Size

25 ML
$201.60
100 ML
$413.00

$201.60

List Price$288.00Save 30%

In StockDetails

Request a Bulk Order
All Photos(2)

Select a Size

Change View
25 ML
$201.60
100 ML
$413.00

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
assay:
≥99%

$201.60

List Price$288.00Save 30%

In StockDetails

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

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
00228KS

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
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
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service