Ethyl 4-dimethylaminobenzoate
[CAS# 10287-53-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl 4-dimethylaminobenzoate
• Synonyms: Ethyl p-N,N-dimethylaminobenzoate
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• CAS Registry Number: 10287-53-3
• EC Number: 233-634-3
• SMILES: CCOC(=O)C1=CC=C(C=C1)N(C)C

Properties

• Density: 1.061
• Melting point: 62-65 °C
• Boiling point: 190-191 °C (14 mmHg)
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS08;GHS09 Danger
• Risk Statements: H360-H411
• Safety Statements: P203-P273-P280-P318-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	1B	H360
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	1B	H360F
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Ethyl 4-dimethylaminobenzoate is an organic compound with the chemical formula C₁₁H₁₅NO₂, widely used as a photoinitiator in the polymerization of light-cured materials. This compound, commonly referred to as EDMAB, plays a crucial role in the field of photopolymerization, particularly in the production of dental materials, coatings, and adhesives. Its discovery and development have significantly advanced the efficiency and versatility of photoinitiated polymerization processes.

The synthesis of ethyl 4-dimethylaminobenzoate can be traced back to the mid-20th century when research into photoinitiators for use in UV-curable materials was intensifying. EDMAB is derived from 4-dimethylaminobenzoic acid through an esterification reaction with ethanol. The resulting compound possesses a benzene ring substituted with a dimethylamino group and an ethyl ester, giving it the necessary photoreactivity to function effectively as a photoinitiator.

Ethyl 4-dimethylaminobenzoate is particularly effective as a co-initiator in combination with other photoinitiators such as benzoin ethers or acyl phosphine oxides. When exposed to UV light, EDMAB absorbs energy and interacts with other photoinitiators to produce free radicals. These free radicals initiate the polymerization of monomers and oligomers in light-curable resins, leading to the formation of solid polymers. This process is essential in applications where rapid curing and precise control over polymerization are required.

One of the primary applications of EDMAB is in the dental industry, where it is used in light-curable dental composites and adhesives. The ability of EDMAB to rapidly initiate polymerization under UV or visible light allows for the efficient curing of dental restoratives, ensuring strong and durable bonds in dental work. The use of EDMAB in these materials enhances the mechanical properties of dental composites, making them resistant to wear and degradation over time.

In addition to its use in dental materials, ethyl 4-dimethylaminobenzoate is also employed in the production of UV-curable coatings and inks. The rapid curing facilitated by EDMAB enables the development of coatings with excellent hardness, adhesion, and resistance to chemicals. These properties make UV-curable coatings ideal for use in various industries, including automotive, electronics, and packaging, where high-performance coatings are essential for protecting surfaces and enhancing product durability.

Ethyl 4-dimethylaminobenzoate is also valuable in the production of adhesives, particularly in applications where rapid bonding is required. The use of EDMAB in UV-curable adhesives allows for the fast and efficient bonding of materials such as glass, metal, and plastic, making it suitable for use in a wide range of industrial and consumer products.

Overall, ethyl 4-dimethylaminobenzoate has proven to be a highly effective photoinitiator, driving advancements in the field of photopolymerization. Its discovery and application have enabled the development of materials with superior performance characteristics, contributing to the growth of industries reliant on light-curable technologies.

References

1989. Hardness of restorative resins: effect of camphorquinone, amine, and inhibitor. Acta Odontologica Scandinavica, 47(4).
DOI: 10.3109/00016358909007706

2022. Meta-analytical analysis on components released from resin-based dental materials. Clinical Oral Investigations, 26(10).
DOI: 10.1007/s00784-022-04625-4

2024. Evidence for widespread human exposure to food contact chemicals. Journal of Exposure Science & Environmental Epidemiology, 34(5).
DOI: 10.1038/s41370-024-00718-2