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226351

Sigma-Aldrich

N-Hydroxymaleimide

97%, for peptide synthesis

Synonym(s):

1-Hydroxypyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C4H3NO3
CAS Number:
4814-74-8
Molecular Weight:
113.07
Beilstein:
1524594
EC Number:
225-385-4
MDL number:
MFCD00005501
UNSPSC Code:
12352005
PubChem Substance ID:
24853562
NACRES:
NA.22

product name

N-Hydroxymaleimide, 97%

Quality Level

200

Assay

97%

form

solid

reaction suitability

reaction type: Addition Reactions

mp

130-133 °C (dec.) (lit.)

application(s)

peptide synthesis

functional group

imide
maleimide

SMILES string

ON1C(=O)C=CC1=O

InChI

1S/C4H3NO3/c6-3-1-2-4(7)5(3)8/h1-2,8H

InChI key

BUXKULRFRATXSI-UHFFFAOYSA-N

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General description

N-Hydroxymaleimide (NHMI) is an organic compound that is widely used as an oxidizing agent in organic synthesis. It is frequently used to selectively oxidize thiols to disulfides and in the synthesis of α, β-unsaturated carbonyl compounds. It can also act as a Michael acceptor and is used in the synthesis of peptides and proteins.

Application

N-Hydroxymaleimide can be used as an oxidant to generate N-hydroxy anilines in situ, which serve as key intermediates in the selective coupling reaction of N-substituted anilines with hydroxylamine derivatives, for the efficient synthesis of aromatic oximes.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

JAN Code

226351-250G:
226351-1G:
226351-VAR:
226351-BULK:
226351-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC3003
BCBW0273
BCBH2786V
1451856V
1451856

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Jamerson Carneiro de Oliveira et al.
Molecules (Basel, Switzerland), 25(2) (2020-01-16)
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Journal of controlled release : official journal of the Controlled Release Society, 267, 119-132 (2017-04-17)
Biological drugs are exquisitely tailored components offering the advantages of high specificity and efficacy that are considered safe for treating diseases. Nevertheless, the effectiveness of biological drugs is limited by their inherent short biological half-life and poor stability in vivo.

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