Merck
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219126

Sigma-Aldrich

β-Butyrolactone

98%

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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:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
B10360855201332615
β-Butyrolactone 98%

Sigma-Aldrich

219126

β-Butyrolactone

γ-Butyrolactone ReagentPlus®, ≥99%

Sigma-Aldrich

B103608

γ-Butyrolactone

refractive index

n20/D 1.411 (lit.)

refractive index

n20/D 1.436 (lit.)

refractive index

-

refractive index

-

bp

71-73 °C/29 mmHg (lit.)

bp

204-205 °C (lit.)

bp

-

bp

-

mp

−43.5 °C (lit.)

mp

−45 °C (lit.)

mp

74-78 °C (lit.)

mp

180-182 °C (lit.)

density

1.056 g/mL at 25 °C (lit.)

density

1.12 g/mL at 25 °C (lit.)

density

-

density

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

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

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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Noureddine Ajellal et al.
Chemical communications (Cambridge, England), 46(7), 1032-1034 (2010-02-04)
Grafting of [Ln(BH(4))(3)(THF)(3)] (Ln = La, Nd) onto silica affords materials containing well-identified bis(borohydride) surface species. The neodymium-decorated silica converts the beta-butyrolactone monomer into highly isotactic poly(beta-hydroxybutyrate). Under similar conditions, the molecular precursor gives rise to an atactic polymer.
Z G Arkin et al.
Journal of biomaterials science. Polymer edition, 12(3), 297-305 (2001-08-04)
The reactions of (R,S) beta-butyrolactone with L-alanine and related oligopeptides (Ala-Ala-Ala) were investigated. The resulting water-soluble oligomers were composed of poly[(R,S)-3-hydroxybutanoic acid] (a-PHB) covalently conjugated to L-alanine and Ala-Ala-Ala oligopeptide. The other chain end was of the carboxylic acid type.
beta-Butyrolactone.
IARC monographs on the evaluation of carcinogenic risks to humans, 71 Pt 3, 1317-1318 (1999-09-07)
Fang-qiong Li et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(31), 10351-10359 (2010-08-06)
Cocaine use and relapse involves learned associations between cocaine-associated environmental contexts and discrete stimuli and cocaine effects. Initially, these contextual and discrete cues undergo memory consolidation after being paired with cocaine exposure. During abstinence, cocaine cue memories can undergo memory
Cuiling Xu et al.
Chemical communications (Cambridge, England), 48(54), 6806-6808 (2012-06-07)
An ethoxy-bridged dinuclear indium catalyst was used for the ring opening polymerization of the cyclic ester β-butyrolactone to form the biodegradable polyester poly(hydroxybutyrate) (PHB). The catalyst shows remarkable activity and control during polymerization, allowing for formation of diblock polymers. Addition

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