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Merck

129585

Maleimide

99%

Synonym(s):

2,5-Pyrroledione

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About This Item

Empirical Formula (Hill Notation):
C4H3NO2
CAS Number:
541-59-3
Molecular Weight:
97.07
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847914
EC Number:
208-787-4
Beilstein/REAXYS Number:
106910
MDL number:
MFCD00005494
Assay:
99%
Form:
powder

Key Documents

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InChI key

PEEHTFAAVSWFBL-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1NC(=O)C=C1

assay

99%

form

powder

mp

91-93 °C (lit.)

functional group

maleimide

Quality Level

200

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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.

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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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.

129585-25G: + 129585-5KG: + 129585-BULK: + 129585-2G: + 129585-VAR: + 129585-10G:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6517
STBK6044
STBK3888
STBK1393
STBJ8641

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Tetrahedron Letters, 48, 4413-4413 (2007)
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
Meng Ke et al.
PLoS computational biology, 13(6), e1005603-e1005603 (2017-06-16)
GLUT1 facilitates the down-gradient translocation of D-glucose across cell membrane in mammals. XylE, an Escherichia coli homolog of GLUT1, utilizes proton gradient as an energy source to drive uphill D-xylose transport. Previous studies of XylE and GLUT1 suggest that the
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
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