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49667

Sigma-Aldrich

4-(Maleinimido)phenyl isocyanate

purum, ≥97.0% (CHN)

Synonym(s):

N-(4-Isocyanatophenyl)maleimide, PMPI

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About This Item

Empirical Formula (Hill Notation):
C11H6N2O3
CAS Number:
123457-83-0
Molecular Weight:
214.18
MDL number:
MFCD00270900
UNSPSC Code:
12352106
PubChem Substance ID:
57651217
NACRES:
NA.25

grade

purum

assay

≥97.0% (CHN)

form

solid

reaction suitability

reagent type: linker

mp

120-125 °C

functional group

maleimide

storage temp.

2-8°C

SMILES string

O=C(C=C1)N(C(C=C2)=CC=C2N=C=O)C1=O

InChI

1S/C11H6N2O3/c14-7-12-8-1-3-9(4-2-8)13-10(15)5-6-11(13)16/h1-6H

InChI key

OJQSISYVGFJJBY-UHFFFAOYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

A novel heterobifunctional linker for hydroxyl-to-thiol coupling

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Stéphane G Lévesque et al.
Bioconjugate chemistry, 18(3), 874-885 (2007-04-04)
Hydrogels derived from synthetic polymers have been previously engineered to degrade under the activity of matrix metalloproteinases (MMPs). It is believed that these systems can act as extracellular-matrix (ECM) equivalents mimicking the degradation and remodeling of the ECM through the
M E Annunziato et al.
Bioconjugate chemistry, 4(3), 212-218 (1993-05-01)
p-Maleimidophenyl isocyanate (PMPI, 1) is a heterobifunctional cross-linking agent useful for thiol to hydroxyl coupling. Several maleimide-activated compounds were prepared and characterized and then shown to be reactive with thiol-containing proteins. Examples include activation of vitamin B12, digoxigenin, digitoxigenin, estradiol
B N Manjula et al.
The Journal of biological chemistry, 275(8), 5527-5534 (2000-02-22)
Bis(maleidophenyl)-PEG2000 (Bis-Mal-PEG2000), a new bifunctional protein cross-linker targeted to sulfhydryl groups, introduces intra-tetrameric cross-links into oxy-HbA in nearly quantitative yields. Structural as well as crystallographic analyses of the cross-linked species, Bis-Mal-PEG2000 HbA, identified Cys-93(beta) as the site of intramolecular cross-linking.
T-W Cha et al.
Analytical biochemistry, 311(1), 27-32 (2002-11-21)
High-density poly(ethylene glycol) (PEG) molecules are grafted onto Si surfaces in a brush-like configuration. We demonstrate that this surface is an excellent substrate for oligonucleotide immobilization. p-Maleimidophenyl isocyanate is used as a heterobifunctional cross-linker to tether thiol-modified oligonucleotides to terminal
Carlos Marcuello et al.
Langmuir : the ACS journal of surfaces and colloids, 34(32), 9376-9386 (2018-07-25)
Atomic force microscopy (AFM) experiments with functionalized tips are currently one of the most powerful tools to locally measure adhesion forces via single-molecule force spectroscopy (SMFS) measurements. The main difficulty is to precisely control the attachment of biomolecules to the
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