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V209

Sigma-Aldrich

δ-Valerolactam

98%

Synonym(s):

delta-Valerolactam, 2-Piperidone

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About This Item

Empirical Formula (Hill Notation):
C5H9NO
CAS Number:
675-20-7
Molecular Weight:
99.13
Beilstein:
106434
EC Number:
211-622-9
MDL number:
MFCD00006037
UNSPSC Code:
12352100
PubChem Substance ID:
24900726
NACRES:
NA.22

Assay

98%

bp

256 °C (lit.)
81-82 °C/0.1 mmHg (lit.)

mp

38-40 °C (lit.)

SMILES string

O=C1CCCCN1

InChI

1S/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)

InChI key

XUWHAWMETYGRKB-UHFFFAOYSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T Senda et al.
The Journal of organic chemistry, 66(21), 6852-6856 (2001-10-13)
Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv
Jingwei Zhang et al.
ACS synthetic biology, 6(5), 884-890 (2017-04-18)
ε-Caprolactam and δ-valerolactam are important commodity chemicals used in the manufacture of nylons, with millions of tons produced annually. Biological production of these highly valued chemicals has been limited due to a lack of enzymes that cyclize ω-amino fatty acid
P A Reddy et al.
Journal of medicinal chemistry, 40(1), 44-49 (1997-01-03)
A series of 3-substituted 2-piperidinone (delta-valerolactam) and hexahydro-2H-azepin-2-one (epsilon-caprolactam) derivatives were prepared and evaluated as anticonvulsants in mice. In the 2-piperidinone series, 3,3-diethyl compound 7b is the most effective anticonvulsant against pentylenetetrazole-induced seizures (ED50, 37 mg/kg; PI (TD50/ED50), 4.46), and
Sungyeon Jang et al.
ACS synthetic biology, 8(6), 1276-1283 (2019-05-11)
Caprolactam is a monomer used for the synthesis of nylon-6, and a recombinant microbial strain for biobased production of nylon-6 was recently developed. An intracellular biosensor for caprolactam can facilitate high-throughput metabolic engineering of recombinant microbial strains. Because of the
Hiroshi Tsuchikawa et al.
Organic letters, 14(9), 2326-2329 (2012-04-26)
Chiral 2-piperidinone compounds with various C-6 substituents were successfully synthesized via a Pd-catalyzed asymmetric 6-endo cyclization of dienamides, which were evidently activated by both N-p-toluenesulfonyl and C-3 ester substituents.
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