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Key Documents

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129585

Sigma-Aldrich

Maleimide

99%

Sinónimos:

2,5-Pyrroledione

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About This Item

Fórmula empírica (notación de Hill):
C4H3NO2
Número de CAS:
541-59-3
Peso molecular:
97.07
Beilstein/REAXYS Number:
106910
EC Number:
208-787-4
MDL number:
MFCD00005494
UNSPSC Code:
12352100
PubChem Substance ID:
24847914
NACRES:
NA.22

Quality Level

200

assay

99%

form

powder

mp

91-93 °C (lit.)

functional group

maleimide

SMILES string

O=C1NC(=O)C=C1

InChI

1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)

InChI key

PEEHTFAAVSWFBL-UHFFFAOYSA-N

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General description

Maleimide (2,5-Pyrroledione) is a new nanoparticle surface functional group which favors easy conjugation with cell penetration peptides. The conjugation is enabled via click chemistry to preserve its biofunctions.

Maleimide is used as a dienophile in Diels Alder reaction for the synthesis of macromolecules.

Application

Rhodium-catalyzed conjugate arylation with arylboronic acids.
The maleimide-functionalized silica beads were used to immobilize the bovine serum albumin (BSA)-boronic acid (BA) conjugates.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

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Tetrahedron Letters, 48, 4413-4413 (2007)
The furan/maleimide Diels--Alder reaction: A versatile click--unclick tool in macromolecular synthesis
Gandini A.
Progress in Polymer Science, 38, 1-29 (2013)
Guangxue Feng et al.
Small (Weinheim an der Bergstrasse, Germany), 10(6), 1212-1219 (2013-12-18)
Single-chain conjugated polymer (CP) dots embedded nanoparticles (NPs) bearing cell penetration peptide (TAT) as surface ligands are synthesized for long term cancer cell tracing applications. The CPNPs are fabricated by matrix-encapsulation method and the embedded CPs can be modulated into
Satya Nandana Narla et al.
Biochemical and biophysical research communications, 443(2), 562-567 (2013-12-12)
We report bovine serum albumin (BSA)-boronic acid (BA) conjugates as lectin mimetics and their glyco-capturing capacity. The BSA-BA conjugates were synthesized by amidation of carboxylic acid groups in BSA with aminophenyl boronic acid in the presence of EDC, and were
Paulo L Onuchic et al.
Scientific reports, 9(1), 12161-12161 (2019-08-23)
Liquid-liquid phase separation (LLPS) of RNA-protein complexes plays a major role in the cellular function of membraneless organelles (MLOs). MLOs are sensitive to changes in cellular conditions, such as fluctuations in cytoplasmic ion concentrations. To investigate the effect of these
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