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389579

Sigma-Aldrich

δ-Valerolactone

technical grade

Synonym(s):

delta-Valerolactone, Tetrahydro-2H-2-pyranone

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About This Item

Empirical Formula (Hill Notation):
C5H8O2
CAS Number:
542-28-9
Molecular Weight:
100.12
Beilstein:
106436
EC Number:
208-807-1
MDL number:
MFCD00006645
UNSPSC Code:
12352100
PubChem Substance ID:
24864292
NACRES:
NA.22

grade

technical grade

form

liquid

impurities

<25% polymer

refractive index

n20/D 1.457 (lit.)

bp

226-229 °C (lit.)
58-60 °C/0.5 mmHg (lit.)

mp

−13-−12 °C (lit.)

density

1.079 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

O=C1CCCCO1

InChI

1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2

InChI key

OZJPLYNZGCXSJM-UHFFFAOYSA-N

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Application

δ-Valerolactone (tetrahydro-2H-2-pyranone or δ VL) can be used as a monomer unit in the synthesis of poly(δ-valerolactone)s poly(conjugated ester)s via ring-opening polymerization.
It can also be used as a starting material in the synthesis of (+)-guadinomic acid , sodium δ-hydroxyvalerate , methyl δ-hydroxyvalerate , and 5-hydroxyvaleraldehyde.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °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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Alice E van der Ende et al.
Journal of the American Chemical Society, 130(27), 8706-8713 (2008-06-12)
We present the synthesis of discrete functionalized polyester nanoparticles in selected nanoscale size dimensions via a controlled intermolecular chain cross-linking process. The novel technique involves the controlled coupling of epoxide functionalized polyesters with 2,2'-(ethylenedioxy)bis(ethylamine) to give well-defined nanoparticles with narrow
Motofumi Osaki et al.
The Journal of organic chemistry, 74(5), 1858-1863 (2009-02-03)
BETA-cyclodextrin (beta-CD)-based nanosphere 1 initiated the oligomerization of delta-valerolactone (delta-VL) on the surface of 1 to give oligo(delta-VL)-tethered beta-CD nanosphere 2 in bulk. Atomic force microscopy indicated that the molecular size of 2 is twice that of 1. The addition
Helen Lee et al.
Biomacromolecules, 6(6), 3119-3128 (2005-11-15)
Six amphiphilic diblock copolymers based on methoxy poly(ethylene glycol) (MePEG) and poly(delta-valerolactone) (PVL) with varying hydrophilic and hydrophobic block lengths were synthesized via a metal-free cationic polymerization method. MePEG-b-PVL copolymers were synthesized using MePEG with Mn = 2000 or Mn
Faquan Zeng et al.
Bioconjugate chemistry, 17(2), 399-409 (2006-03-16)
Epidermal growth factor (EGF)-conjugated copolymer micelles were prepared from a mixture of diblock copolymers of methoxy poly(ethylene glycol)-block-poly(delta-valerolactone) (MePEG-b-PVL) and EGF-PEG-b-PVL for targeted delivery to EGF receptor (EGFR)-overexpressing cancers. The block copolymers and functionalized block copolymers were synthesized using PEG
K N Houk et al.
The Journal of organic chemistry, 73(7), 2674-2678 (2008-03-08)
gamma-Butyrolactone, unlike delta-valerolactone, does not polymerize despite a strain energy of approximately 8 kcal mol-1 which could be relieved by opening the s-cis lactone ester bond to an s-trans ester bond in the polymer. To explain this anomaly, we have
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