ChemicalBook > CAS DataBase List > N-Succinimidyl 3-maleimidopropionate

N-Succinimidyl 3-maleimidopropionate

Product Name
N-Succinimidyl 3-maleimidopropionate
CAS No.
55750-62-4
Chemical Name
N-Succinimidyl 3-maleimidopropionate
Synonyms
2,5-Dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate;3-MALEIMIDOPROPIONIC ACID N-SUCCINIMIDYL ESTER;(2,5-Dioxopyrrolidin-1-yl) 3-(2,5-dioxopyrrol-1-yl)propanoate;BMPS Crosslinker;Mal-beta-Ala-OSu;Cross-linkingReagent;MaleiMide-(CH2)2-NHS;NHS-(CH2)2-Mal (BMPS);3-Maleimidopropionic acid NHS;3-Maleimido-propionic NHS este
CBNumber
CB7132511
Molecular Formula
C11H10N2O6
Formula Weight
266.21
MOL File
55750-62-4.mol
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N-Succinimidyl 3-maleimidopropionate Property

Melting point:
168-170 °C(lit.)
Boiling point:
448.8±47.0 °C(Predicted)
Density 
1.55±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,2-8°C
solubility 
Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
-2.39±0.20(Predicted)
color 
White to Light Brown
Appearance
white crystals
Water Solubility 
Insoluble in water.
Sensitive 
Moisture Sensitive
BRN 
1492578
InChI
InChI=1S/C11H10N2O6/c14-7-1-2-8(15)12(7)6-5-11(18)19-13-9(16)3-4-10(13)17/h1-2H,3-6H2
InChIKey
JKHVDAUOODACDU-UHFFFAOYSA-N
SMILES
N1(CCC(ON2C(=O)CCC2=O)=O)C(=O)C=CC1=O
CAS DataBase Reference
55750-62-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
37
Safety Statements 
26-36/37/39-24/25
WGK Germany 
3
F 
10-21
HS Code 
29280000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H335May cause respiratory irritation

Precautionary statements

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
63179
Product name
3-(Maleimido)propionic acid N-hydroxysuccinimide ester
Purity
≥98.5% (HPLC)
Packaging
25mg
Price
$225
Updated
2025/07/31
Sigma-Aldrich
Product number
63179
Product name
3-(Maleimido)propionic acid N-hydroxysuccinimide ester
Purity
≥98.5% (HPLC)
Packaging
100mg
Price
$682
Updated
2025/07/31
Sigma-Aldrich
Product number
358657
Product name
3-Maleimidopropionic acid N-hydroxysuccinimide ester
Purity
99%
Packaging
25mg
Price
$217
Updated
2025/07/31
TCI Chemical
Product number
S0427
Product name
N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent]
Purity
>98.0%(HPLC)(N)
Packaging
100mg
Price
$73
Updated
2025/07/31
TCI Chemical
Product number
S0427
Product name
N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent]
Purity
>98.0%(HPLC)(N)
Packaging
1g
Price
$219
Updated
2025/07/31
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N-Succinimidyl 3-maleimidopropionate Chemical Properties,Usage,Production

Description

3-Maleimido-propionic NHS ester contains a maleimide group and an NHS ester. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Chemical Properties

White to off-white solid

Uses

3-Maleimidopropionic acid N-hydroxysuccinimide ester is a reagent that is widely used for generating stable maleimide-activated carrier proteins that can spontaneously react with sulfhydryls. Alternatively these relatively stable maleimide-activated intermediates may be lyophilized and stored for later conjugation to a hapten.

Uses

A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent, N-Succinimidyl 3-maleimidopropionate can also been used in immunodiagnostics.

reaction suitability

reagent type: linker

Synthesis

108-31-6

6066-82-6

107-95-9

55750-62-4

Example 1: Synthesis of NHS esters of N-maleimidopropionic acid 1. Maleic anhydride, β-alanine (1 mole equivalent) and acetonitrile (ACN, 25 v/v) were added to a reaction vessel under nitrogen protection to form a slurry. 2. The slurry was heated to 70 °C and kept stirring for 5-8 hours. 3. After completion of the reaction, cooled to 5 °C, N-hydroxybutanediimide (NHS, 1 mole equivalent) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI, 1 mole equivalent) were added sequentially. 4. After maintaining the temperature at 0-5 °C for 1 hour of reaction, EDCI (1 molar equivalent) was added again. 5. The reaction mixture was heated to 70 °C and kept stirring for 7 hours. 6. At the end of the reaction, the mixture was cooled to 20 °C and concentrated under vacuum at a temperature not exceeding 45 °C until the rate of solvent distillation was significantly reduced. 7. Dichloromethane (DCM, 40 v/v) was added to the residue and stirred until completely dissolved. 8. The organic phase was washed sequentially with 12% w/w aqueous ammonium chloride (25 wt. eq.) and 24% w/w aqueous sodium chloride (25 wt. eq.). 9. Add magnesium sulfate (1 w/w) to dry the organic solution and stir for 1-2 hours at ambient temperature. 10. Vacuum filtered to remove inorganic salts and the filter cake was washed with DCM (4 v/v). 11. Vacuum concentrate the filtrate while gradually replacing the DCM with isopropyl acetate (IPAC). 12. The resulting slurry was cooled to ambient temperature, stirred for 1 hour and vacuum filtered. 13. The product filter cake was washed with IPAC (4 v/v) and subsequently rotary dried under vacuum at 40 °C to constant weight to give an off-white solid product. 14. Typical yields were 60-80% of the theoretical maximum yield. Product characterization: 1H NMR (400 MHz, d6-DMSO): δ 2.80 (4H, br s), δ 3.05 (2H, t, J~7 Hz), δ 3.75 (2H, t, J~7 Hz), δ 7.05 (2H, s).

IC 50

Non-cleavable Linker

References

[1] Patent: WO2011/23680, 2011, A2. Location in patent: Page/Page column 13-14
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10198 - 10201
[3] Angew. Chem., 2015, vol. 127, p. 10336 - 10339
[4] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10582 - 10585
[5] Journal of the American Chemical Society, 2004, vol. 126, # 3, p. 734 - 735

N-Succinimidyl 3-maleimidopropionate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Succinimidyl 3-maleimidopropionate manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
N-Succinimidyl 3-maleimidopropionate 55750-62-4
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000KGS
Release date
2025-09-18
Henan Aochuang Chemical Co.,Ltd.
Product
N-Succinimidyl 3-maleimidopropionate 55750-62-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-26
Zhuozhou Wenxi import and Export Co., Ltd
Product
N-Succinimidyl 3-maleimidopropionate 55750-62-4
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

55750-62-4, N-Succinimidyl 3-maleimidopropionateRelated Search:

N-Succinimidyl 6-maleimidohexanoate N-Chlorosuccinimide Bismaleimide Methyl acrylate Succinimide BUTYL OLEATE N-Hydroxysuccinimide Tris(trimethylsilyl)phosphate O-Phthalimide 3-(4-Hydroxyphenyl)propionic acid DIALIFOS N-Ethylmaleimide 3-Maleimidopropionic acid N-PROPYLMALEIMIDE Maleimide 2-OXOCYCLOHEXANECARBONITRILE 3-Acryloylamino-1-propanol solution, 50% in water MALEIMIDOPROPIONIC ACID N-HYDROXYSULPHOSUCCINIMIDE ESTER

  • N-(3-MALEIMIDOPROPIONYLOXY)SUCCINIMIDE
  • N-MALEOYL-BETA-ALANINE N'-HYDROXYSUCCINIMIDE ESTER
  • N-SUCCINIMIDYL 3-MALEIMIDOPROPIONATE
  • 3-MALEIMIDOPROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER
  • 3-MALEIMIDOPROPIONIC ACID N-SUCCINIMIDYL ESTER
  • MALEIMIDOPROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER
  • 3-Maleidopropionic acid N-hydroxysuccynimide ester (SMP)
  • B-MALEIMIDOPROPIONIC ACID N-*HYDROXYSUCCINIMIDE ESTE
  • Cross-linkingReagent
  • N-Succinimidyl3-maleinimidopropionate
  • N-SUCCINIMIDYL3-MALEIMIDOPROPIONATE[CROSS-LINKINGREAGENT]
  • MaleiMide-(CH2)2-NHS
  • NSM N-SucciniMidyl 3-MaleiMidopropionate
  • 3-MaleiMidopropionic acid N-succiniMidyl ester (BMPS)
  • 2,5-Dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate
  • BMPS Crosslinker
  • N[b-Maleimdopropxyloxy]succinimade ester
  • Mal-beta-Ala-OSu
  • 3-Maleimido-propionic NHS ester
  • 3-(Maleimido)propionic acid N-hydroxysuccinimide ester, >=98%
  • BMPS N-Succinimidyl 3-maleimidopropionate
  • (2,5-Dioxopyrrolidin-1-yl) 3-(2,5-dioxopyrrol-1-yl)propanoate
  • 2,5-Dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)
  • 3-Maleimidopropionic acid NHS≥ 99.5% (HPLC)
  • Succinimidyl 3-maleimidopropionate
  • 3-Maleimidopropionic acid N-hydroxysuccinimide ester *CAS 55750-62-4*
  • 3-Maleimidopropionic acid succinimidyl ester
  • 3-Maleimidopropionic acid NHS
  • 3-Maleimidopropionic acid-NHS ester
  • N-(3-Maleimidopropionyloxy)succinimide, N-Succinimidyl 3-maleimidopropionate, BMPS, N-Maleoyl-β-alanine Nμ-hydroxysuccinimide ester, N-Maleoyl-β-alanine N-hydroxysuccinimide ester
  • 3-(Maleimido)propionic acid N-succinimidyl ester, BMPS, N-(3-Maleimidopropionyloxy)succinimide, N-Maleoyl-β-alanine Nμ-hydroxysuccinimide ester, N-Succinimidyl 3-maleimidopropionate
  • 1-[3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropyl]-1H-pyrrole-2,5-dione
  • 2,5-Dioxo-2,5-dihydro-1H-pyrrole-1-propionic acid 2,5-dioxo-1-pyrrolidinyl ester
  • 2,5-Dioxo-3-pyrroline-1-propionic acid 2,5-dioxopyrrolidine-1-yl ester
  • 2,5-Dioxo-3-pyrroline-1-propionic acid succinimidyl ester
  • 3-(2,5-Dioxo-1H-pyrrole-1-yl)propanoic acid succinimidyl ester
  • 3-(2,5-Dioxo-3-pyrroline-1-yl)propanoic acid succinimidyl ester
  • 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-propanoic Acid 2,5-Dioxo-1-pyrrolidinyl Ester
  • N-SucciniMidyl 3-(N-MaleiMido)propionate
  • 3-Maleimidopropionic Acid N-Succinimidyl Ester N-(3-Maleimidopropionyloxy)succinimide
  • N-Maleoyl-β-alanine N-hydroxysuccinimide ester
  • N-Maleoyl-β-alanine Nμ-hydroxysuccinimide ester
  • NHS-(CH2)2-Mal (BMPS)
  • N-Succinimidyl 3-maleimidopropionate(BMPS)
  • N-Succinimidyl3-Maleimidopropionate，2，5-Dioxo-1-pyrrolidinyl3-(2，5-Dioxo-2，5-dihydro-1-pyrrolyl)propionate
  • N-Succinimidyl3-Maleimidopropionate[Cross-linkingReagent]&gt
  • 3-(Maleimido)propionic acid N-hydroxysuccinimide ester, 99%, reagent grade
  • BMPS N-Succinimidyl 3-maleimidopropionate,98%
  • 3-Maleimido-propionic NHS este
  • 1H-Pyrrole-1-propanoic acid, 2,5-dihydro-2,5-dioxo-, 2,5-dioxo-1-pyrrolidinyl ester
  • MPS (NHS-3-maleimidopropionate)
  • N-β-maleimidopropyl-oxysuccinimide ester
  • [MAL-SPA] N-Succinimidyl 3-maleimide propionate
  • 3-maleimide propionic acid hydroxysuccinimide ester
  • 3-Maleimidopropionic acid hydroxysuccinimide ester
  • N-(3-Maleimidopropionyloxy)succinimide, N-Maleoyl-β-alanine N′-hydroxysuccinimide ester, N-Maleoyl-β-alanine N-hydroxysuccinimide ester, N-Succinimidyl 3-maleimidopropionate, BMPS
  • N-Succinimidyl 3-maleimido-propanoate
  • 3-Maleimidopropionic acid <i>N</i>-hydroxysuccinimide ester