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178098

Sigma-Aldrich

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
EC Number:
214-340-4
MDL number:
MFCD00006670
UNSPSC Code:
12352100
PubChem Substance ID:
24850719
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

178098-100G:
178098-BULK:
178098-5G:
178098-VAR:
178098-25G:

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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Alexander A Bisset et al.
Chemical communications (Cambridge, England), 48(98), 11978-11980 (2012-11-07)
The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in
Deevi Basavaiah et al.
Organic & biomolecular chemistry, 6(6), 1034-1039 (2008-03-11)
A simple and convenient synthesis of di(E)-arylidene-tetralone-spiro-glutarimides from Baylis-Hillman acetates via an interesting biscyclization strategy involving facile C-C and C-N bond formation is described. Also, one-pot multistep transformation of the Baylis-Hillman acetates into di(E)-arylidene-spiro-bisglutarimides is presented.
Pei-Qiang Huang et al.
Organic letters, 8(7), 1435-1438 (2006-03-28)
[reaction: see text] Using 5b as a common intermediate, the first asymmetric synthesis of (-)-epiquinamide (4) and a formal asymmetric synthesis of (-)-homopumiliotoxin 223G (2) is described. A key feature of our approach is the flexible introduction of a functionalized
Chuanjin Tian et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(45), 14305-14313 (2012-10-16)
The significance of the molecular chirality of drugs has been widely recognized due to the thalidomide tragedy. Most of the new drugs reaching the market today are single enantiomers, rather than racemic mixtures. However, many optically pure drugs, including thalidomide
Jianhua Ju et al.
Organic letters, 9(25), 5183-5186 (2007-11-14)
Lactimidomycin (LTM, 1) is a macrolide antitumor antibiotic with a glutarimide side chain from Streptomyces amphibiosporus ATCC53964. To further develop LTM and related analogues as drug candidates we have (i) improved LTM production by approximately 20 fold, (ii) identified three
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