N-Succinimidyl 4-(p-Maleimidophenyl)butyrate

Basic Information

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CAS Number

79886-55-8

Molecular Formula

C18H16N2O6

Molecular Weight

356.33 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

129.0 to 133.0 deg-C

SMILES

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C1CC(=O)N(C1=O)OC(=O)CCCC2=CC=C(C=C2)N3C(=O)C=CC3=O

InChI

InChI=1S/C18H16N2O6/c21-14-8-9-15(22)19(14)13-6-4-12(5-7-13)2-1-3-18(25)26-20-16(23)10-11-17(20)24/h4-9H,1-3,10-11H2

InChIKey

PMJWDPGOWBRILU-UHFFFAOYSA-N

LogP

1.0458999999999998

Topological Polar Surface Area

101.06 Å²

Hydrogen Bond Donor/Acceptor

0 / 8

Complexity

629

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

Synonyms & References

English

D92274
Benzenebutanoic acid, 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-, 2,5-dioxo-1-pyrrolidinyl ester
N-Succinimidyl 4-(4-Maleimidophenyl)butyrate, >/=97%
SMPB Cross linker
DTXSID601000817
PMJWDPGOWBRILU-UHFFFAOYSA-N
4-(4-Maleimidophenyl)butyric Acid N-Succinimidyl Ester
SCHEMBL43979
2,5-Dioxopyrrolidin-1-yl4-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)butanoate
Succinimidyl 4-(4-maleimidophenyl)butyrate
PS50 Cpd
4-N-Maleimidophenyl butanoic acid-NHS
(2,5-dioxopyrrolidin-1-yl) 4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoate
SMPB
N-Succinimidyl 4-[4-maleimidophenyl]butyrate
N-Succinimidyl 4-(4-maleimidophenyl)butyrate
succinimidyl 4-(p-maleimidophenyl)butyrate
A9933
1-(4-{4-[(2,5-Dioxopyrrolidin-1-yl)oxy]-4-oxobutyl}phenyl)-1H-pyrrole-2,5-dione
1H-Pyrrole-2,5-dione, 1-(4-(4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxobutyl)phenyl)-
4-(4-Maleimidophenyl)butyric acid NHS ester
NSC344484
SMPB Cross-linker
MFCD00054961
2,5-dioxopyrrolidin-1-yl 4-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]butanoate
NSC 344484
4-(4-Maleimidophenyl)butyric acid N-hydroxysuccinimide ester
SMPB Crosslinker
AS-74026
79886-55-8
2,5-Dioxopyrrolidin-1-yl 4-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)butanoate

MDL Number

MFCD00054961

FAQ

What are the physical and chemical properties of N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8)?

N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8) is a white to off-white crystalline solid with a molecular weight of approximately 314.3 g/mol. It is sparingly soluble in water but soluble in organic solvents like DMF and DMSO. The compound is highly reactive towards amine functionalities, making it useful for conjugation reactions. It features both succinimidyl and maleimide groups, which enhance its reactivity and specificity in bioconjugation applications.

How is N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8) typically synthesized?

N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8) is typically synthesized by the condensation of succinimidyl butyrate with 4-maleimidophenyl boronic acid in the presence of a base like triethylamine. The reaction yields the desired product with good selectivity and yield. The process involves careful monitoring of pH and temperature to optimize the reaction conditions.

What industries use N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8)?

N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8) is widely used in various industries including pharmaceuticals for drug conjugation, biotechnology for protein labeling, polymer science for modifying surfaces, and sensor technology for developing bioactive sensors. It is also utilized in semiconductor manufacturing for functionalizing substrates. Its ability to form stable covalent bonds with amines makes it a valuable reagent in these applications.

What precautions should be taken when handling N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8)?

When handling N-Succinimidyl 4-(p-Maleimidophenyl)butyrate (CAS: 79886-55-8), it is important to wear appropriate personal protective equipment (PPE) including gloves, safety goggles, and a lab coat. The compound should be used in a well-ventilated area or under a fume hood due to its reactive nature. Spills should be cleaned up promptly using appropriate absorbent materials. Always consult the Material Safety Data Sheet (MSDS) or safety data sheet (SDS) for specific handling and disposal instructions. Handling this compound should be done with caution to prevent skin and eye irritation.