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
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
Safety
- HS Code
- 2925.19.4200
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.
N-Bromosuccinimide Price
- Product number
- M3143
- Product name
- 2-Maleimidoacetic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 50mg
- Price
- $64
- Updated
- 2025/07/31
- Product number
- M3143
- Product name
- 2-Maleimidoacetic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 250mg
- Price
- $188
- Updated
- 2025/07/31
- Product number
- M124990
- Product name
- MaleimidoaceticAcid
- Packaging
- 250mg
- Price
- $135
- Updated
- 2021/12/16
- Product number
- 39668
- Product name
- 2-Maleimidoaceticacid,98%(HPLC)
- Purity
- 98%(HPLC)
- Packaging
- 50MG
- Price
- $73.92
- Updated
- 2021/12/16
- Product number
- 39668
- Product name
- 2-Maleimidoaceticacid,98%(HPLC)
- Purity
- 98%(HPLC)
- Packaging
- 250MG
- Price
- $250.88
- Updated
- 2021/12/16
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
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View Lastest Price from 2-Maleimido acetic acid manufacturers
- 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
- 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
- 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