488216
3,4-Dihydroxy-1-butene
≥99%
Synonym(s):
3-Butene-1,2-diol
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About This Item
Linear Formula:
CH2=CHCH(OH)CH2OH
CAS Number:
Molecular Weight:
88.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-835-1
Beilstein/REAXYS Number:
1633578
MDL number:
Assay:
≥99%
Product Name
3,4-Dihydroxy-1-butene, ≥99%
InChI key
ITMIAZBRRZANGB-UHFFFAOYSA-N
InChI
1S/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2
SMILES string
OCC(O)C=C
assay
≥99%
bp
195 °C/733 mmHg (lit.)
density
1.047 g/mL at 25 °C (lit.)
functional group
hydroxyl
Quality Level
Related Categories
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.
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
Storage Class
10 - Combustible liquids
wgk
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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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
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.
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
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