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219126

Sigma-Aldrich

β-Butyrolactone

98%

Synonym(s):

beta-Butyrolactone, β-Methyl-β-propiolactone, 3-Hydroxybutyric acid β-lactone, 4-Methyl-2-oxetanone

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About This Item

Empirical Formula (Hill Notation):
C4H6O2
CAS Number:
3068-88-0
Molecular Weight:
86.09
EC Number:
221-330-3
MDL number:
MFCD00005170
UNSPSC Code:
12352100
PubChem Substance ID:
24853107
NACRES:
NA.22

Quality Level

100

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

H226,H315,H319,H351

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

140.0 °F - closed cup

Flash Point(C)

60 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Hori et al.
International journal of biological macromolecules, 25(1-3), 237-245 (1999-07-23)
The mechanism of the ring-opening polymerisation of beta-butyrolactones was studied. The ring-opening polymerisation of BL catatlysed by distannoxane complexes is of a living nature. The polymerisation of racemic BL gave a predominantly syndiotactic P(3HB). The temperature effect on syndiospecificity was
Valentin Poirier et al.
Dalton transactions (Cambridge, England : 2003), (44)(44), 9820-9827 (2009-11-04)
A new heteroleptic ethyl-zinc complex stabilized by a chelating bis(morpholinomethyl)phenoxy ligand has been synthesised and shown to be a highly potent initiator for the immortal ring-opening polymerisation (ROP) of lactide and beta-butyrolactone, being able to convert up to 50,000 equiv.
Noureddine Ajellal et al.
Dalton transactions (Cambridge, England : 2003), 39(36), 8363-8376 (2010-04-29)
This Perspective article summarizes efforts paid in our group to develop efficient metal-based catalysts for the immortal ring-opening polymerization (iROP) of cyclic esters in the presence of large amounts of alcohols (ROH) as chain transfer agents. The catalyst systems reviewed
Z Jedliński et al.
International journal of biological macromolecules, 25(1-3), 247-253 (1999-07-23)
Novel feasibility of fuctionalized poly(3-hydroxybutanoic acid), PHB, and its copolymers synthesis via ring-opening of beta-butyrolactone (ROP) mediated by activated anionic initiators or enzymes in vitro is presented. Using these new synthetic approaches, PHB with defined chemical structure of the end
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))
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