Description
GoldBio’s 1-Acetyl-3-carboxaldehyde is a bifunctional aromatic compound used as a building block in organic synthesis, heterocycle construction, and fluorescent dye development.
With both aldehyde and ketone groups, it enables efficient formation of Schiff bases, hydrazones, and other condensation products. Researchers use this reagent in the synthesis of bioactive molecules, ligands, and fluorescent probes, as well as in studies of reaction mechanisms and stereoelectronic effects.
GoldBio’s 1-Acetyl-3-carboxaldehyde is ideal for medicinal chemistry, organic method development, and advanced analytical applications.
Functional Highlights and Mechanism
-
The aldehyde functional group (–CHO) at the 3-position of the indole ring allows for reactive conjugation or further chemical transformations (e.g., Schiff base formation, reductive amination, derivatization) making it a versatile building block.
-
The acetyl substituent at the 1-position modifies the electronic character of the indole core, which may impact reactivity or binding in downstream probe/sensor design or heterocyclic synthetic pathways.
-
As an indole derivative, this compound may serve as a starting point in the synthesis of fluorescent probes, heterocyclic ligands, or biologically-relevant small molecules. For example, it has been cited as a reactant in preparation of RNA-specific fluorescent probes.
Recommended Applications and Usage Notes
Recommended Applications
-
Use as a synthetic intermediate in heterocyclic chemistry, particularly in indole derivative synthesis.
-
Use as a building block in fluorescent or luminescent probe development (e.g., derivatization of the indole carboxaldehyde to yield imaging dyes).
-
Use in conjugation chemistry where aldehyde functionality is needed for coupling to amines or hydrazides, forming labeled biomolecules or sensors.
-
Use in medicinal-chemistry workflows exploring indole scaffolds or structure–activity relationship (SAR) series involving indole derivatives.
-
Use in lab reagent libraries where defined small-molecule building blocks are needed for assay development, small molecule synthesis or chemical biology.
Usage Tips and Considerations
-
When dissolving, select an appropriate solvent (likely organic: e.g., DMSO, DMF, acetone) because indole aldehydes may have limited aqueous solubility. Consult COA or test solubility.
-
Verify the aldehyde remains intact (no oxidation to acid) by analytical methods (HPLC, NMR), especially if stored long term.
-
Protect from moisture and strong oxidizing agents (these may degrade aldehyde functionality or cause side reactions). SDS indicates incompatibility with strong oxidizing agents.
-
Use appropriate personal protective equipment (PPE) when handling: gloves, eye protection, in fume hood if dust or vapors may form (SDS warns of respiratory irritation).
-
For downstream reaction/formulation, control conditions (temperature, pH, reagent equivalence) to avoid side-reactions (e.g., self-condensation of aldehyde) or polymerization.
-
Store in tightly closed container at ambient temperature (per GoldBio spec) but consider storing in the dark and dry environment to maximize shelf life.
Safety Disclaimer
This product is intended strictly for laboratory research use only. It is not intended for human therapeutic, diagnostic or veterinary use. Before use, consult the Safety Data Sheet (SDS) provided for detailed hazard, handling, storage and disposal instructions. According to the SDS:
-
Causes skin irritation (H315) and serious eye irritation (H319).
-
May cause respiratory irritation (H335) upon inhalation of dust or vapors.
-
Avoid breathing dust/fume/gas/mist/vapors/spray; wear protective gloves/eye/face protection.
Dispose of this compound and any residuals in accordance with local, state and federal regulations.
1-Acetyl-3-Carboxaldehyde
MOLECULAR BIOLOGY GRADE
Formula: C11H9NO2
MW: 187.20 g/mol
Storage/Handling: Store at room temperature.
PubChem Chemical ID: 89915
Powered by Bioz