ChemicalBook > CAS DataBase List > 2-Maleimido acetic acid

2-Maleimido acetic acid

Product Name: 2-Maleimido acetic acid
CAS No.: 25021-08-3
Chemical Name: 2-Maleimido acetic acid
Synonyms: 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid;NSC 266055;N-Maleoylglycine;N-MaleiMidoglycine;N,N-maleoyl-glycine;MALEIMIDOACETIC ACID;2-maleimide acetic acid;2-MALEIMIDO ACETIC ACID;N-(CarboxyMethyl)MaleiMide;2-MALEIMIDO ACETIC ACID 97%
CBNumber: CB61118111
Molecular Formula: C6H5NO4
Formula Weight: 155.11
MOL File: 25021-08-3.mol

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2-Maleimido acetic acid Property

Melting point:: 114 °C(Solv: chloroform (67-66-3))
Boiling point:: 376.7±25.0 °C(Predicted)
Density: 1.578±0.06 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: soluble in DMSO, Methanol
form: powder to crystal
pka: 3.31±0.10(Predicted)
color: White to Almost white
InChI: InChI=1S/C6H5NO4/c8-4-1-2-5(9)7(4)3-6(10)11/h1-2H,3H2,(H,10,11)
InChIKey: GBKPNGVKZQBPCZ-UHFFFAOYSA-N
SMILES: N1(CC(O)=O)C(=O)C=CC1=O

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Safety

HS Code: 2925.19.4200

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical

Product number: M3143
Product name: 2-Maleimidoacetic Acid
Purity: >98.0%(HPLC)(T)
Packaging: 50mg
Price: $64
Updated: 2025/07/31

TCI Chemical

Product number: M3143
Product name: 2-Maleimidoacetic Acid
Purity: >98.0%(HPLC)(T)
Packaging: 250mg
Price: $188
Updated: 2025/07/31

TRC

Product number: M124990
Product name: MaleimidoaceticAcid
Packaging: 250mg
Price: $135
Updated: 2021/12/16

Chem-Impex

Product number: 39668
Product name: 2-Maleimidoaceticacid,98%(HPLC)
Purity: 98%(HPLC)
Packaging: 50MG
Price: $73.92
Updated: 2021/12/16

Chem-Impex

Product number: 39668
Product name: 2-Maleimidoaceticacid,98%(HPLC)
Purity: 98%(HPLC)
Packaging: 250MG
Price: $250.88
Updated: 2021/12/16

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2-Maleimido acetic acid Chemical Properties,Usage,Production

Chemical Properties

White to Almost white powder to crystal or Pale Yellow Solid.

Uses

Maleimidoacetic Acid (CAS# 25021-08-3) is a heterocyclic organic compound that has a variety of uses in organic synthesis. It contains both a maleimide and carboxylic acid functional group, making it a versatile reagent for coupling reactions with amine-containing compounds.

Application

2-Maleimido acetic acid is a maleimide-containing ligand that could be used to produce the cisplatin-based Pt(IV) complexes (OC-6-44)-diamminedichlorido(ethanolato)(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetato)platinum(IV) and (OC-6-44)-acetatodiamminedichlorido(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetato)platinum(IV). The Pt(IV) complexes are considered to act as antitumor prodrugs and their in vivo activity can be improved by exploiting drug targeting and delivery strategies[1]. In this case, conjugation between maleimide-containing Pt(IV) prodrugs and furan or furan-containing drug delivery vectors via Diels-Alder cycloaddition.

Synthesis

329709-87-7

25021-08-3

In a 1000 mL three-necked flask, compound (II) (162 g, 0.94 mol, X = 1) and 400 mL of dichloromethane were added, followed by triethylamine (284.8 g, 2.82 mol). The reaction mixture was cooled in an ice-salt bath and the temperature was maintained at -2 °C with stirring. Phenyl 4-nitrilotrifluoroacetate (353.4 g, 1.5 mol) dissolved in 300 mL of dichloromethane was then added slowly dropwise, with the rate of dropwise acceleration controlled to maintain the reaction temperature between -5 and 10 °C. After titration was completed, the reaction mixture was continued to be stirred at the same temperature for 3 hours. After completion of the reaction, the reaction solution was concentrated to dryness. To the residue was added 400 mL of water and the pH was adjusted to 3-4 with concentrated hydrochloric acid under stirring. the resulting 4-nitrophenol was removed by filtration and the filtrate was extracted three times with dichloromethane. The organic phases were combined, washed with water and dried with anhydrous magnesium sulfate. The dried organic phase was concentrated to give 129 g of a pale yellow solid. The solid was recrystallized with a mixed solvent of ethyl acetate and petroleum ether to give 107 g of white solid. After drying, it was weighed as 94 g. The purity was determined by HPLC to be 98.2% and the yield was 64.5%.

References

[1] Gabano E, et al. Conjugation between maleimide-containing Pt(IV) prodrugs and furan or furan-containing drug delivery vectors via Diels-Alder cycloaddition. Inorganica Chimica Acta, 2019; 488: 195-200.

2-Maleimido acetic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-Maleimido acetic acid manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: 2-Maleimido acetic acid 25021-08-3
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: 2-Maleimido acetic acid 25021-08-3
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

Career Henan Chemical Co

Product: 2-Maleimido acetic acid 25021-08-3
Price: US $9.80/KG
Min. Order: 1g
Purity: ≥99%
Supply Ability: 100kg
Release date: 2020-01-08

25021-08-3, 2-Maleimido acetic acidRelated Search:

DISUCCINIMIDYL SUBERATE Suberate Bis(sulfosuccinimidyl) Sodium Salt N-Succinimidyl maleimidoacetate 3-(BENZOPHENONE-4-CARBOXAMIDO)-2-MALEIMIDOPROPANOIC ACID 2-Maleimido acetic acid 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-4-methanesulfonylbutanoic acid 2-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-PROPIONIC ACID 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-phenylpropanoic acid 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-methylbutanoic acid DACM 3-MALEIMIDO-4-METHYL-6,7-METHYLENEDIOXYCOUMARIN RARECHEM AL CD 0491 4-carbamoyl-2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-methylpentanoic acid 9-ACETOXY-2-(4-(2,5-DIHYDRO-2,5-DIOXO-1H-PYRROL-1-YL)-3-OXO-3-H-NAPHTHO[2,1-B]PYRAN 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-(1H-imidazol-4-yl)propanoic acid 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-4-methylpentanoic acid methyl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

2-MALEIMIDOACETIC ACID DIHYDRATE

N-Maleoylglycine

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-acetic Acid

N-(CarboxyMethyl)MaleiMide

N-MaleiMidoglycine

NSC 266055

2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

MAA 2-Maleimido acetic acid

2-MALEIMIDO ACETIC ACID 97%

2-(2,5-dioxopyrrol-1-yl)acetic acid

2-Maleimido acetic acid(MAA)

1H-Pyrrole-1-acetic acid, 2,5-dihydro-2,5-dioxo-

2-maleimide acetic acid

2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-acetic acid

MALEIMIDOACETIC ACID

2-MALEIMIDO ACETIC ACID

N,N-maleoyl-glycine

25021-08-3

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