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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
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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.)

functional group

ester

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)[1]. Polymerization of racemic β-butyrolactone in the presence of chiral initiators has been reported[2]. 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[3].

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7606
MKCN4283
MKBZ4944V
MKBJ3709V
04028EJ

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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.
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
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
Variably isotactic poly(hydroxybutyrate) from racemic beta-butyrolactone: microstructure control by achiral chromium(III) salophen complexes.
Manuela Zintl et al.
Angewandte Chemie (International ed. in English), 47(18), 3458-3460 (2008-04-05)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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