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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

Signal Word

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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
Luciano Dibona-Villanueva et al.
Journal of agricultural and food chemistry, 69(3), 945-954 (2021-01-14)
A novel chemical conjugate between chitosan (CH) and riboflavin (RF) has been synthesized and characterized via Fourier transform infrared, NMR, and other spectroscopic methods. Photophysical and photochemical properties such as absorption spectra, fluorescence emission, fluorescence anisotropy, and singlet oxygen generation
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