Tris(dimethylaminomethyl)phenol
[CAS# 90-72-2]

Identification

• Classification: Natural product >> Natural phenols
• Name: Tris(dimethylaminomethyl)phenol
• Synonyms: 2,4,6-Tris(dimethylaminomethyl)phenol; DMP-30
• Molecular Formula: C₁₅H₂₇N₃O
• Molecular Weight: 265.40
• CAS Registry Number: 90-72-2
• EC Number: 202-013-9
• SMILES: CN(C)CC1=CC(=C(C(=C1)CN(C)C)O)CN(C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 0.973 g/mL
• Index of Refraction: 1.548, Calc.^*, 1.516
• Boiling Point: 320.5±0.0 ºC (760 mmHg), Calc.^*, 130-135 ºC (1 mmHg)
• Flash Point: 116.6±25.2 ºC, Calc.^*, 124 ºC

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H314-H315-H318-H319-H411
• Precautionary Statements: P260-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P330-P332+P317-P337+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1C	H314
Skin sensitization	Skin Sens.	1B	H317
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1	H314
Acute toxicity	Acute Tox.	5	H303
Acute toxicity	Acute Tox.	5	H313
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1A	H314

Discovory and Applicatios

Tris(dimethylaminomethyl)phenol, often abbreviated as TDAMP, is an organic compound that belongs to the family of phenolic compounds, characterized by the presence of three dimethylaminomethyl groups attached to a phenolic ring. The discovery of TDAMP occurred in the mid-20th century during research into phenolic compounds for industrial applications. This compound is notable for its unique chemical structure, which enhances its reactivity and suitability for various applications, particularly in the field of polymer chemistry.

The synthesis of TDAMP typically involves the reaction of formaldehyde with dimethylamine and phenol, resulting in a compound that exhibits both phenolic and amine characteristics. This dual functionality allows TDAMP to participate in a range of chemical reactions, making it a valuable intermediate in the synthesis of other compounds. Its discovery was motivated by the need for more efficient curing agents and additives in epoxy resins and other thermosetting polymers.

One of the primary applications of TDAMP is as a hardener or curing agent in epoxy resins. When used in conjunction with epoxy compounds, TDAMP enhances the cross-linking process, leading to improved mechanical properties, thermal stability, and chemical resistance of the final product. This application is particularly valuable in industries such as construction, automotive, and aerospace, where durable and high-performance materials are essential.

In addition to its role in epoxy formulations, TDAMP serves as a stabilizer and modifier in the production of polyurethane and phenolic resins. Its ability to promote cross-linking and improve thermal stability makes it an attractive option for manufacturers looking to enhance the performance of their products. The incorporation of TDAMP into polyurethane systems can result in improved flexibility, strength, and resistance to degradation, making it suitable for applications in coatings, adhesives, and sealants.

Another significant application of TDAMP is in the field of biocides and antimicrobial agents. The presence of dimethylamino groups contributes to its effectiveness against various microbial species. As a result, TDAMP is incorporated into formulations designed to inhibit the growth of bacteria, fungi, and other pathogens in a range of products, including paints, coatings, and personal care items.

Despite its advantages, the use of TDAMP requires careful consideration of safety and environmental factors. While it is generally recognized as safe for use in various applications, regulatory assessments are essential to ensure that products containing TDAMP meet safety standards. Ongoing research is focused on evaluating its toxicity and potential environmental impact, particularly in consumer products.

The versatility of TDAMP has also sparked interest in its potential applications beyond traditional uses. Researchers are exploring its effectiveness in drug delivery systems, where its amine functionality may enhance the solubility and bioavailability of pharmaceutical compounds. The ability of TDAMP to form complexes with metal ions also opens avenues for its use in catalysis and materials science.

In conclusion, tris(dimethylaminomethyl)phenol is a valuable compound with a range of applications in polymer chemistry, biocides, and potential biomedical uses. Its unique chemical structure and reactivity make it an essential ingredient in the production of high-performance materials and formulations. As research continues to uncover its potential in new applications, TDAMP remains an important compound in modern chemistry and industry.