60444-78-2

Basic information

• Product Name: SUCCINIMIDYL 4-FORMYLBENZOATE
• Synonyms: N-Succinimidyl 4-formylbenzoate;4-[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]benzaldehyde;4-Carboxybenzaldehyde N-HydroxysucciniMide Ester;Benzaldehyde, 4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-;SucciniMidyl 4-forMylbenzoate(4-SFB);2,5-Dioxopyrrolidin-1-yl 4-forMylbenzoate;SFB (crosslinking agent);N-Succinimidyl 4-Formylbenzoate
• CAS NO: 60444-78-2
• Molecular Formula: C₁₂H₉NO₅
• Molecular Weight: 247.2
• Product Categories: Nitric Oxide Reagents;Cross Linking Reagents;Aldehydes;Building Blocks;C10-C12;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Cyclic Imides;Esters;Organic Building Blocks
• Mol File: 60444-78-2.mol

Chemical Properties

• Melting Point: 163°C
• Boiling Point: 425.4°C at 760 mmHg
• Flash Point: 211.1°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 1.92E-07mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: −20°C
• Solubility: methanol: soluble50mg/mL, clear to very faintly turbid, colorles
• CAS DataBase Reference: SUCCINIMIDYL 4-FORMYLBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: SUCCINIMIDYL 4-FORMYLBENZOATE(60444-78-2)
• EPA Substance Registry System: SUCCINIMIDYL 4-FORMYLBENZOATE(60444-78-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 60444-78-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
SUCCINIMIDYL 4-FORMYLBENZOATE is used as a crosslinking agent for the covalent attachment of biomolecules, such as proteins and peptides, to other molecules or surfaces. Its reactive amino group allows for the formation of stable amide bonds, making it a versatile tool in chemical synthesis and bioconjugation.
Used in Pharmaceutical Industry:
SUCCINIDYL 4-FORMYLBENZOATE is used as a key intermediate in the synthesis of various pharmaceutical compounds, including drugs and drug delivery systems. Its ability to form stable covalent bonds with biologically active molecules makes it a valuable component in the development of new therapeutic agents.
Used in Research and Development:
In the field of research and development, SUCCINIMIDYL 4-FORMYLBENZOATE is used as a reagent for the modification and functionalization of biomolecules. This allows scientists to study the structure, function, and interactions of these molecules in greater detail, leading to a better understanding of biological processes and the development of novel therapeutic strategies.
Used in Diagnostics:
SUCCINIMIDYL 4-FORMYLBENZOATE is used as a component in the development of diagnostic tools, such as immunoassays and biosensors. Its ability to form stable covalent bonds with target molecules enables the creation of highly specific and sensitive detection systems for various analytes, including proteins, nucleic acids, and small molecules.
Used in Material Science:
In the field of material science, SUCCINIMIDYL 4-FORMYLBENZOATE is used as a crosslinking agent to improve the properties of various materials, such as polymers and hydrogels. Its ability to form stable covalent bonds with different types of molecules allows for the creation of materials with enhanced mechanical, chemical, and biological properties, making them suitable for a wide range of applications, from drug delivery to tissue engineering.

InChI:InChI=1/C12H9NO5/c14-7-8-1-3-9(4-2-8)12(17)18-13-10(15)5-6-11(13)16/h1-4,7H,5-6H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 619-66-9 4-Carboxybenzaldehyde 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Downstream Products

• 1254054-75-5 C₄₃H₅₀N₄O₉S₂ 
• 1415408-70-6 C₃₅H₅₉NO₁₆ 

Relevant articles and documents

FRET-based cyanine probes for monitoring ligation reactions and their applications to mechanistic studies and catalyst screening

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Efficient Pictet–Spengler Bioconjugation with N-Substituted Pyrrolyl Alanine Derivatives

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Bio-orthogonal Coupling as a Means of Quantifying the Ligand Density on Hydrophilic Quantum Dots

We describe the synthesis of two metal-coordinating ligands that present one or two lipoic acid (LA) anchors, a hydrophilic polyethylene glycol (PEG) segment and a terminal reactive group made of an azide or an aldehyde, two functionalities with great utility in bio-orthogonal coupling techniques. These ligands were introduced onto the QD surfaces using a combination of photochemical ligation and mixed cap exchange strategy, where control over the fraction of azide and aldehyde groups per nanocrystal can be easily achieved: LA-PEG-CHO, LA-PEG-N3, and bis(LA)-PEG-CHO. We then demonstrate the application of two novel bio-orthogonal coupling strategies directly on luminescent quantum dot (QD) surfaces that use click chemistry and hydrazone ligation under catalyst-free conditions. We applied the highly efficient hydrazone ligation to couple 2-hydrozinopyridine (2-HP) to aldehyde-functionalized QDs, which produces a stable hydrazone chromophore with a well-defined optical signature. This unique optical feature has enabled us to extract a measure for the ligand density on the QDs for a few distinct sizes and for different ligand architectures, namely mono-LA-PEG and bis(LA)-PEG. We found that the foot-print-area per ligand was unaffected by the nanocrystal size but strongly depended on the ligand coordination number. Additionally, we showed that when the two bio-orthogonal functionalities (aldehyde and azide) are combined on the same QD platform, the nanocrystal can be specifically reacted with two distinct targets and with great specificity. This design yields QD platforms with distinct chemoselectivities that are greatly promising for use as carriers for in vivo imaging and delivery.

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A method for the preparation of superparamagnetic iron oxide nanoparticle-porphyrin (SPION-TPP) conjugates through click chemistry, which can be used as novel theranostic nanoagents for photodynamic therapy is developed. The synthesis, characterisation, and evaluation of the photocytotoxicity profiles of the nanoconjugates prepared is reported. Upon light irradiation, SPION-TPP nanoconstructs promote a photodynamic effect in vitro in murine amelanotic melanoma B78-H1 cells, with IC50 values in the region of 800 nm, similarly to unbound TPP, whereas they remain non-cytotoxic in the dark. However, these nanoconstructs show poor cellular uptake, which influences a linear dose-response effect. Therefore, the improvement of delivery to cells has also been studied by conjugating a well-known cell-penetrating peptide (TAT peptide) to the SPION-TPP nanoparticles. The new nanoconstructs show lower IC50 values (in the region of 500 nm) and a clear dose-response effect. Our results suggest that TAT-conjugated SPION-TPP nanoparticles are efficient nanodevices both for tracking drugs by means of magnetic resonance imaging (MRI)-based techniques and for treating cancer cells through photodynamic therapy, thus functioning as promising theranostic nanoagents.

Proline-modified DNA as catalyst of the aldol reaction

(Chemical Equation Presented) Unbound reactant: Proline-modified DNA acts as catalyst of the intramolecular aldol reaction between a complementary aldehyde and free non-tethered ketones (see scheme). The results of these studies extend the methodological repertoire of DNA-templated reactions.

Efficient γ-amino-proline-derived cell penetrating peptide-superparamagnetic iron oxide nanoparticle conjugates via aniline-catalyzed oxime chemistry as bimodal imaging nanoagents

Aniline-catalyzed oxime chemistry was employed to conjugate a γ-amino-proline-derived cell penetrating peptide to superparamagnetic iron oxide nanoparticles (SPIONs). Internalization of the novel nanoconjugate into HeLa cells was found to be remarkably higher compared to the analogous TAT-SPION conjugate.

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Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination

Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.

A METHOD FOR LABELING OF ALDEHYDE CONTAINING TARGET MOLECULES

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