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Merck
CN

389579

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24864292
EC Number:
208-807-1
Beilstein/REAXYS Number:
106436
MDL number:
MFCD00006645
Form:
liquid

Key Documents

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Product Name

δ-Valerolactone, technical grade

InChI key

OZJPLYNZGCXSJM-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1CCCCO1

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.)

functional group

ester

storage temp.

−20°C

Quality Level

100

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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

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBK3235
STBH4365
STBD6123V
STBC2634V
S39463V

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Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation
Reid BT, et al.
The Journal of Organic Chemistry, 83(16), 9492-9496 (2018)
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
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
Three-component reductive alkylation of 2-hydroxy-1, 4-naphthoquinones with lactols
Kim EE, et al.
Tetrahedron Letters, 57(8), 864-867 (2016)
Ryo Shintani et al.
Organic letters, 11(16), 3754-3756 (2009-07-30)
A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application
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