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Safety Information

488216

Sigma-Aldrich

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:
497-06-3
Molecular Weight:
88.11
Beilstein:
1633578
EC Number:
207-835-1
MDL number:
MFCD00239410
UNSPSC Code:
12352100
PubChem Substance ID:
24872379
NACRES:
NA.22

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. 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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

488216-100ML:
488216-BULK:
488216-25ML:
488216-500ML:
488216-VAR:
488216-1L:

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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)
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
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