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
Beilstein:
1633578
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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. 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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
R J Krause et al.
Drug metabolism and disposition: the biological fate of chemicals, 25(8), 1013-1015 (1997-08-01)
Incubations of butadiene monoxide (BMO) with mouse, rat, and human liver microsomes or cDNA-expressed human microsomal epoxide hydrolase led to 3-buten-1,2-diol (BDD) detection; the BDD peak exhibited a GC/MS fragmentation pattern similar to that of reference material. Incubations with rat
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