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178098

Glutarimide

98%

Synonym(s):

2,6-Piperidinedione, NSC 58190

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About This Item

Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
1121-89-7
Molecular Weight:
113.11
NACRES:
NA.22
PubChem Substance ID:
24850719
UNSPSC Code:
12352100
EC Number:
214-340-4
MDL number:
MFCD00006670
Assay:
98%
Form:
solid
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Quality Level

200

assay

98%

form

solid

mp

155-157 °C (lit.)

SMILES string

O=C1CCCC(=O)N1

InChI

1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)

InChI key

KNCYXPMJDCCGSJ-UHFFFAOYSA-N

General description

A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.

Application

Reactant for:
Thionations
Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture
Synthesis of β-adrenoceptor ligands
Enantioselective synthesis of securinega alkaloids
Intramolecular amidocyclopropanation reactions
Synthesis of alpha-fluoro-alpha amino amides

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000546413
0000546415
0000546415
0000546413
0000482873

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Yohsuke Watanabe et al.
Organic letters, 12(2), 268-271 (2009-12-22)
The boron aldol reaction of beta-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr(2)EtN or Et(3)N affords enantiomeric lactone product.
Matthew Hoffmann et al.
Cancer chemotherapy and pharmacology, 71(2), 489-501 (2012-12-04)
To investigate the pharmacokinetics and disposition of [(14)C]pomalidomide following a single oral dose to healthy male subjects. Eight subjects were administered a single 2 mg oral suspension of [(14)C]pomalidomide. Blood (plasma), urine and feces were collected. Mass balance of radioactivity
Cai-Yun Geng et al.
Journal of computational chemistry, 29(5), 686-693 (2007-09-13)
The reaction mechanism of the Rh-catalyzed [4 + 2] annulation of 4-alkynals with isocyanates is unraveled using density functional calculations. The reaction mechanisms of the model system and the real substituted system have been investigated and the results are compared.
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Global Trade Item Number

SKUGTIN
178098-25G04061833544860
178098-5G04061833320365