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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

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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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
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
Organolanthanide-initiated living polymerizations of ε -caprolactone, δ-valerolactone, and β-propiolactone
Yamashita M, et al.
Macromolecules, 29(5), 1798-1806 (1996)
Three-component reductive alkylation of 2-hydroxy-1, 4-naphthoquinones with lactols
Kim EE, et al.
Tetrahedron Letters, 57(8), 864-867 (2016)
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)
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