4-(N,N-Dimethylamino)butanal dimethyl acetal
[CAS# 19718-92-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 4-(N,N-Dimethylamino)butanal dimethyl acetal
• Synonyms: N,N-Dimethyl-4-aminobutanal dimethyl acetal
• Molecular Formula: C₈H₁₉NO₂
• Molecular Weight: 161.24
• CAS Registry Number: 19718-92-4
• EC Number: 606-363-7
• SMILES: CN(C)CCCC(OC)OC

Properties

• Density: 0.892
• Boiling point: 163.9 °C
• Flash point: 25.4 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

4-(N,N-Dimethylamino)butanal dimethyl acetal, often abbreviated as DMABDA, was discovered during investigations into acetal-protected amines for their utility in organic synthesis and medicinal chemistry. The compound was synthesized to stabilize the reactive 4-(N,N-dimethylamino)butanal through acetalization, a common technique used to protect aldehydes by converting them into less reactive acetals. Researchers synthesized DMABDA by reacting 4-(N,N-dimethylamino)butanal with methanol in the presence of an acid catalyst, forming the dimethyl acetal as a protected intermediate. This discovery highlighted the utility of acetal-protected amino aldehydes in various chemical transformations, offering a stable intermediate for further derivatization and applications.

DMABDA serves as a versatile intermediate in organic synthesis, particularly in the formation of complex molecules. Its stability under mild conditions allows it to undergo various transformations, such as reductive amination or nucleophilic addition, to form amines, imines, and other derivatives. This makes it valuable for synthesizing complex organic compounds in research and industrial settings. In multi-step synthesis, DMABDA acts as a protected form of 4-(N,N-dimethylamino)butanal. The acetal group can be selectively removed under acidic conditions, revealing the aldehyde functionality when needed for subsequent reactions. This protective strategy facilitates the selective manipulation of reactive sites in complex synthetic pathways, improving yields and simplifying purification.

DMABDA is used in the development of pharmaceuticals, particularly as a building block for synthesizing biologically active molecules. Its ability to form stable intermediates makes it useful in the design and synthesis of small-molecule drugs targeting various diseases. Researchers can incorporate DMABDA into molecular scaffolds to explore structure-activity relationships and optimize drug candidates for efficacy and safety. The acetal moiety in DMABDA can be used to design prodrugs, which are inactive compounds that convert into active drugs in the body. The acetal group can mask the active site of a drug, improving its stability, solubility, or bioavailability. Once administered, enzymatic or chemical processes in the body can cleave the acetal, releasing the active drug at the target site, enhancing therapeutic outcomes.

DMABDA is employed in the synthesis of polymers and resins with specific properties. Its reactivity allows it to be incorporated into polymer backbones or side chains, introducing functionalities that impart unique mechanical, thermal, or chemical properties. These polymers can be used in coatings, adhesives, and composite materials, providing enhanced performance and durability.As a functional monomer, DMABDA can be used to create polymers with reactive sites that enable post-polymerization modifications. This approach allows for the fine-tuning of polymer properties, such as hydrophilicity, biocompatibility, or stimuli responsiveness, making them suitable for applications in biomedical devices, sensors, and smart materials.

DMABDA can be used in the synthesis of agrochemicals, particularly as a precursor for creating novel pesticides and herbicides. Its chemical versatility allows for the incorporation of functional groups that target specific pest pathways, leading to the development of selective and effective crop protection agents. The compound's structural features can be leveraged to design plant growth regulators that modulate physiological processes in crops. These regulators can influence seed germination, root development, and stress tolerance, enhancing agricultural productivity and resilience against environmental challenges.

DMABDA is used in the development of chemical probes for studying biological systems and chemical reactions. Its ability to form stable and reactive intermediates makes it useful for designing probes that can investigate enzyme activity, protein interactions, or metabolic pathways in living systems. Researchers explore new synthetic methodologies using DMABDA as a model compound to develop innovative reactions and techniques. Studies focus on optimizing reaction conditions, discovering novel catalytic systems, and exploring the reactivity of acetals under various conditions, contributing to advancements in synthetic organic chemistry.

References

2003. Rizatriptan benzoate. Pharmaceutical Substances. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-18-0042

2003. Sumatriptan. Pharmaceutical Substances. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-19-0112