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Key Documents

408018

Sigma-Aldrich

N-Benzylmaleimide

99%

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About This Item

Empirical Formula (Hill Notation):
C11H9NO2
CAS Number:
Molecular Weight:
187.19
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

mp

70 °C (lit.)

SMILES string

O=C1C=CC(=O)N1Cc2ccccc2

InChI

1S/C11H9NO2/c13-10-6-7-11(14)12(10)8-9-4-2-1-3-5-9/h1-7H,8H2

InChI key

MKRBAPNEJMFMHU-UHFFFAOYSA-N

General description

N-Benzylmaleimide is an N-substituted maleimide and its microwave-mediated facile and fast synthesis has been described. Radical and anionic copolymerization of N-benzylmaleimide with optically active N-(L-menthoxycarbonylmethyl)maleimide has been reported. Base-catalyzed asymmetric cycloaddition of anthrone with N-benzylmaleimide was studied in the presence of C2-chiral pyrrolidines. Stereoselctive iridium-catalyzed double incorporation reaction of styrene with N-benzylmaleimide affords cyclic product.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Iridium-catalyzed double incorporation reaction of N-benzylmaleimide to styrene via ortho-C-H bond activation, initiated by precoordination of the double bond of styrene to iridium.
Kiyooka S-I and Takeshita Y.
Tetrahedron Letters, 46(25), 4279-4282 (2005)
Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines.
Tokioka K, et al.
Tetrahedron Asymmetry, 8(1), 101-107 (1997)
X Wang et al.
Organic letters, 2(22), 3509-3512 (2000-11-18)
[reaction: see text] A new strategy for the synthesis and purification of synthetic intermediates is described using anthracene-tagged ester substrates in conjunction with an N-benzylmaleimide resin. Anthracene chemical tags permit use of standard solution-phase reaction conditions and reaction-monitoring techniques.
Microwave-induced One-pot Synthesis of N-carboxyalkyl Maleimides and Phthalimides.
Borah N, et al.
J. Chem. Res. Synop., 5, 272-273 (1998)
Construction of a single-chain Fv from an antibody which catalyses a Diels Alder cycloaddition.
L Brooks et al.
Biochemical Society transactions, 24(2), 313S-313S (1996-05-01)

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