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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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Ryo Shintani et al.
Organic letters, 14(9), 2410-2413 (2012-04-26)
A palladium-catalyzed decarboxylative cyclopropanation of γ-methylidene-δ-valerolactones with aromatic aldehydes has been developed to give 4-oxaspiro[2.4]heptanes with high selectivity. The site of nucleophilic attack to a π-allylpalladium intermediate has been controlled with a sterically demanding phosphine ligand. The course of the
Diphenyl phosphate as an efficient cationic organocatalyst for controlled/living ring-opening polymerization of δ-valerolactone and ε-caprolactone
Makiguchi K, et al.
Macromolecules, 44(7), 1999-2005 (2011)
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
Organolanthanide-initiated living polymerizations of ε -caprolactone, δ-valerolactone, and β-propiolactone
Yamashita M, et al.
Macromolecules, 29(5), 1798-1806 (1996)
Zuwei Ma et al.
Biomacromolecules, 12(9), 3265-3274 (2011-07-16)
Biodegradable polyurethane urea (PUU) elastomers are ideal candidates for fabricating tissue engineering scaffolds with mechanical properties akin to strong and resilient soft tissues. PUU with a crystalline poly(ε-caprolactone) (PCL) macrodiol soft segment (SS) showed good elasticity and resilience at small
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