All Photos(2)
Synonym(s):
beta-Butyrolactone, β-Methyl-β-propiolactone, 3-Hydroxybutyric acid β-lactone, 4-Methyl-2-oxetanone
Empirical Formula (Hill Notation):
C4H6O2
CAS Number:
Molecular Weight:
86.09
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
98%
refractive index
n20/D 1.411 (lit.)
bp
71-73 °C/29 mmHg (lit.)
mp
−43.5 °C (lit.)
density
1.056 g/mL at 25 °C (lit.)
SMILES string
CC1CC(=O)O1
InChI
1S/C4H6O2/c1-3-2-4(5)6-3/h3H,2H2,1H3
InChI key
GSCLMSFRWBPUSK-UHFFFAOYSA-N
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General description
β-Butyrolactone undergoes ring opening polymerization in the presence of ethoxy-bridged dinuclear indium catalyst to yield biodegradable polyester poly(hydroxybutyrate). Polymerization of racemic β-butyrolactone in the presence of chiral initiators has been reported. It is versatile building block for organic synthesis.
Application
β-Butyrolactone was used in the preparation of (3-O-[oligo-(3-hydroxybutyrate ester)] fluorescein, fluorescein derivative of poly(3-hydroxybutyrate) via anionic polymerization.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2
WGK
WGK 3
Flash Point(F)
140.0 °F
Flash Point(C)
60 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
危险化学品
Certificates of Analysis (COA)
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Highly active, productive, and syndiospecific yttrium initiators for the polymerization of racemic beta-butyrolactone.
Abderramane Amgoune et al.
Angewandte Chemie (International ed. in English), 45(17), 2782-2784 (2006-03-21)
K Hemminki
Chemico-biological interactions, 34(3), 323-331 (1981-03-15)
Reactivity of beta-propiolactone, beta-butyrolactone and gamma-butyrolactone with guanosine, RNA, DNA and 4-(p-nitrobenzyl)pyridine was studied. beta-Propiolactone was 50--100 times more reactive with all the nucleophiles than beta-butyrolactone whereas gamma-butyrolactone was completely inactive. The rate of alkylation by the lactones was guanosine
Lee R Rieth et al.
Journal of the American Chemical Society, 124(51), 15239-15248 (2002-12-19)
Polymerization of beta-butyrolactone (BBL) and beta-valerolactone (BVL) using the zinc alkoxide initiator (BDI-1)ZnO(i)()Pr [(BDI-1) = 2-((2,6-diisopropylphenyl)amido)-4-((2,6-diisopropylphenyl)imino)-2-pentene] proceeds very rapidly under mild conditions to produce poly(3-hydroxybutyrate) (PHB) and poly(3-hydroxyvalerate) (PHV), respectively. For the monomer-to-initiator ratio 200:1, PHB number-average molecular weights (M(n))
Stereoelective Polymerization of β-butyrolactone.
Le Borgne A and Spassky A.
Polymer, 30(12), 2312-2319 (1989)
J T Lee et al.
The Journal of organic chemistry, 66(16), 5424-5426 (2001-08-04)
The PPNCo(CO)(4) and BF(3) x Et(2)O catalyzed carbonylation of simple and functionalized epoxides in DME gives the corresponding beta-lactones regioselectively in good to high yields. The carbonylation occurred selectively at the unsubstituted C-O bond of the epoxide ring, and this
Chromatograms
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