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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
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)
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