ChemicalBook > CAS DataBase List > N-Succinimidyl maleimidoacetate

N-Succinimidyl maleimidoacetate

Product Name: N-Succinimidyl maleimidoacetate
CAS No.: 55750-61-3
Chemical Name: N-Succinimidyl maleimidoacetate
Synonyms: 2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate;Azido-PEG1-Val-Cit-PABC-PNP;MaleiMidoacetic;N-SMP;AMAS, 10 mM in DMSO;a-Maleimidoacetic acid-NHS;N-(α-MaleiMidoacetoxy)succiMide;N-SUCCINIMIDYL MALEIMIDOACETATE;a-MaleiMidoacetic acid-NHS(AMAS);N-(α-Maleimidoacetoxy)succinimide
CBNumber: CB1201178
Molecular Formula: C10H8N2O6
Formula Weight: 252.18
MOL File: 55750-61-3.mol

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N-Succinimidyl maleimidoacetate Property

Melting point:: 174-175°C
Boiling point:: 430.1±47.0 °C(Predicted)
Density: 1.63±0.1 g/cm3(Predicted)
storage temp.: Inert atmosphere,Store in freezer, under -20°C
solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated)
pka: -2.69±0.20(Predicted)
form: Solid
color: White to Off-White
InChI: InChI=1S/C10H8N2O6/c13-6-1-2-7(14)11(6)5-10(17)18-12-8(15)3-4-9(12)16/h1-2H,3-5H2
InChIKey: TYKASZBHFXBROF-UHFFFAOYSA-N
SMILES: N1(CC(ON2C(=O)CCC2=O)=O)C(=O)C=CC1=O
CAS DataBase Reference: 55750-61-3

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 29280000

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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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

Sigma-Aldrich

Product number: M3884
Product name: Maleimidoacetic acid N-hydroxysuccinimide ester
Purity: ≥95%
Packaging: 10mg
Price: $118
Updated: 2025/07/31

TCI Chemical

Product number: S0968
Product name: N-Succinimidyl Maleimidoacetate
Packaging: 20mg
Price: $110
Updated: 2024/03/01

TCI Chemical

Product number: S0968
Product name: N-Succinimidyl Maleimidoacetate
Packaging: 100mg
Price: $314
Updated: 2025/07/31

Cayman Chemical

Product number: 17160
Product name: Maleimidoacetic Acid N-hydroxysuccinimide ester
Purity: ≥95%
Packaging: 5mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 17160
Product name: Maleimidoacetic Acid N-hydroxysuccinimide ester
Purity: ≥95%
Packaging: 10mg
Price: $78
Updated: 2024/03/01

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N-Succinimidyl maleimidoacetate Chemical Properties,Usage,Production

Chemical Properties

White Crystalline Solid

Uses

Maleimidoacetic acid N-hydroxysuccinimide ester is a crosslinking reagent that contains NHS ester- and maleimide-reactive groups at the opposite ends of a 4.4 ? spacer arm. This configuration allows for sequential, two-stage conjugation with amine and sulfhydryl functional groups in the preparation of protein-hapten or protein-protein conjugates.

Uses

A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates.

reaction suitability

reagent type: linker

Synthesis

6066-82-6

17686-36-1

55750-61-3

GENERAL STEPS: To a 500 mL three-necked flask was added N-maleimidoacetic acid (94 g, 0.6 mol) and 300 mL of methylene chloride, followed by oxalyl chloride (90 g, 0.72 mol). The reaction mixture was heated to reflux and a large amount of gas was observed to be released. After 2 hours of reaction, the solution became clarified. Subsequently, dichloromethane and excess oxalyl chloride were removed by concentration. 200 mL of dichloromethane was added to wash and remove the residual acid to give the crude product N-maleimidoacetyl chloride. The crude product was dissolved in 200 mL of dichloromethane. In another vessel, N-hydroxysuccinimide (69 g, 0.6 mol) and triethylamine (80.8 g, 0.8 mol) were dissolved in 300 mL of dichloromethane and the reaction temperature was controlled to be no more than 20° C. under the cooling of an ice water bath. A dichloromethane solution of the above N-maleimidoacetyl chloride was slowly added dropwise to this mixture and the dropwise process lasted for 2 hours. Upon completion of the reaction, the reaction solution was washed with 200 mL of water to remove the triethylamine hydrochloride, followed by 100 mL of 1N hydrochloric acid to remove excess triethylamine, and finally with 200 mL of saturated brine. The organic phase was dried and concentrated to dryness to give 137 g of white solid. Purification by recrystallization in a mixed solvent of ethyl acetate and petroleum ether resulted in 116 g of white solid with 98.7% HPLC purity and 76.7% yield.

IC 50

Non-cleavable Linker

References

[1] Patent: CN105037237, 2017, B. Location in patent: Paragraph 0071-0074

N-Succinimidyl maleimidoacetate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Succinimidyl maleimidoacetate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: N-Succinimidyl maleimidoacetate 55750-61-3
Price: US $0.00-0.00/g
Min. Order: 5g
Purity: 98.13%
Supply Ability: 10kg
Release date: 2025-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: N-Succinimidyl maleimidoacetate 55750-61-3
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: N-Succinimidyl maleimidoacetate 55750-61-3
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

55750-61-3, N-Succinimidyl maleimidoacetateRelated Search:

Chloromethyl ethyl carbonate Diisopropyl chlorophosphate ETHYL CHLOROSULFONATE Suberate Bis(sulfosuccinimidyl) Sodium Salt BUTYL OLEATE Ethyl 2-(Chlorosulfonyl)acetate Maleimide Methyl acrylate O-Phthalimide N-Chlorosuccinimide N-Hydroxysuccinimide Tris(trimethylsilyl)phosphate Succinimide Bismaleimide DIALIFOS 1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE 2-Maleimido acetic acid AC-GLY-OSU

MALEIMIDOACETIC ACID N-HYDROXYSUCCINIMIDE ESTER

N-SUCCINIMIDYL MALEIMIDOACETATE

a-Maleimidoacetic acid-NHS

N-(α-Maleimidoacetoxy)succinimide Ester(AMAS)

1-[2-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]-1H-pyrrole-2,5-dione

N-(α-MaleiMidoacetoxy)succiMide

1H-Pyrrole-2,5-dione, 1-[2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]-

MaleiMidoacetic

a-MaleiMidoacetic acid-NHS(AMAS)

2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetate

AMAS N-Succinimidyl maleimidoacetate

2,5-Dioxopyrrolidin-1-yl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)

N-SMP

N-(α-Maleimidoacetoxy)succinimide

N-SuccinimidylMaleimidoacetate&gt

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

N-(alpha-Maleimidoacetoxy)succinimide

Azido-PEG1-Val-Cit-PABC-PNP

Maleimidyl acetate succinimidyl ester

N-(alfa-Maleimidoacetoxy)succinimide

ADC Linkers,Inhibitor,AMAS,inhibit,Antibody-drug conjugates linkers

(2,5-dioxopyrrolidin-1-yl) 2-(2,5-dioxopyrrol-1-yl)acetate

AMAS, 10 mM in DMSO

N-(α-Maleimidoacetoxy)succinimide

55750-61-3

C10H8N2O6

BioChemical

Proteomics and Protein Expression

Proteomics

Protein Modification

Heterobifunctional Cross-Linking Reagents

Crosslinking

Nitric Oxide Reagents

Cross Linking Reagents

Maleimide Derivatives

Crosslinking

Heterobifunctional Cross-Linking Reagents

Protein Modification

Cross Linking Reagents,Maleimide Derivatives

MTS & Sulfhydryl Active Reagents