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488216

Sigma-Aldrich

3,4-Dihydroxy-1-butene

≥99%

Sinônimo(s):

3-Butene-1,2-diol

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About This Item

Fórmula linear:
CH2=CHCH(OH)CH2OH
Número CAS:
497-06-3
Peso molecular:
88.11
Beilstein:
1633578
Número CE:
207-835-1
Número MDL:
MFCD00239410
Código UNSPSC:
12352100
ID de substância PubChem:
24872379
NACRES:
NA.22

Nível de qualidade

100

Ensaio

≥99%

pb

195 °C/733 mmHg (lit.)

densidade

1.047 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

OCC(O)C=C

InChI

1S/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2

chave InChI

ITMIAZBRRZANGB-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

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.

Aplicação

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302 + H312 + H332

Classificações de perigo

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análise (COA)

Lot/Batch Number
00228KS

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Sigma-Aldrich

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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)
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)
R A Kemper et al.
Chemical research in toxicology, 9(7), 1127-1134 (1996-10-01)
3-Butene-1,2-diol (BDD) is a metabolite of the carcinogenic petrochemical 1,3-butadiene. BDD is produced by cytochrome P450-mediated oxidation of 1,3-butadiene to butadiene monoxide, followed by enzymatic hydrolysis by epoxide hydrolase. The metabolic disposition of BDD is unknown. The current work characterizes
Christopher L Sprague et al.
Toxicological sciences : an official journal of the Society of Toxicology, 80(1), 3-13 (2004-05-07)
3-Butene-1,2-diol (BDD) is a major metabolite of 1,3-butadiene (BD), but the role of BDD in BD toxicity and carcinogenicity remains unclear. In this study, the acute toxicity of BDD was investigated in male Sprague-Dawley rats and B6C3F1 mice. Of the
E Malvoisin et al.
Xenobiotica; the fate of foreign compounds in biological systems, 12(2), 137-144 (1982-02-01)
1. In rat liver microsomes, 1,3-butadiene was metabolized to butadiene monoxide, which was subsequently transformed into 3-butene-1,2-diol by microsomal epoxide hydrolase. 2. In the metabolism of butadiene oxide in microsomes, four metabolites were detected, namely two stereoisomers of DL-diepoxybutane, and
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