N,N-Dimethylbenzylamine
[CAS# 103-83-3]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: N,N-Dimethylbenzylamine
• Synonyms: Benzyldimethylamine; BDMA
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• CAS Registry Number: 103-83-3
• EC Number: 203-149-1
• SMILES: CN(C)CC1=CC=CC=C1

Properties

• Density: 0.9
• Melting point: -75 °C
• Boiling point: 183-184 °C
• Refractive index: 1.5-1.502
• Flash point: 54 °C
• Water solubility: 8 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H332-H312-H302-H314-H412
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P361+P364-P362+P364-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H331
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H331

• Transport Information: UN 2619

Discovery and Applications

N,N-Dimethylbenzylamine is an organic compound that belongs to the class of tertiary amines, featuring a benzyl group attached to a nitrogen atom substituted with two methyl groups. This compound has been widely studied due to its reactivity and versatility in both organic synthesis and industrial applications. Its structure makes it a useful catalyst and a reagent in various chemical reactions, particularly in the production of polymers and fine chemicals.

The discovery of N,N-Dimethylbenzylamine can be traced back to early investigations into amine derivatives and their role in catalysis and organic transformations. Tertiary amines like N,N-Dimethylbenzylamine are known for their nucleophilicity and basicity, properties that are crucial in numerous synthetic pathways. Early research demonstrated that the presence of both the benzyl group and the two methyl groups on the nitrogen atom significantly influenced the compound's reactivity, making it a suitable catalyst for several reactions. As a result, the compound became of interest in fields such as polymer chemistry and the manufacturing of pharmaceuticals and agrochemicals.

One of the primary applications of N,N-Dimethylbenzylamine is its use as a catalyst in polyurethane production. Polyurethanes are essential materials in a wide range of industries, including automotive, construction, and textiles. N,N-Dimethylbenzylamine acts as a catalyst in the reaction between isocyanates and polyols, facilitating the formation of polyurethane foams, coatings, and elastomers. Its ability to accelerate the reaction without undergoing significant side reactions makes it a valuable additive in the production process, ensuring high efficiency and quality in the final product.

In addition to its role in polymer chemistry, N,N-Dimethylbenzylamine is also utilized in organic synthesis. Its nucleophilic properties make it a suitable reagent in alkylation and acylation reactions, where it can promote the formation of carbon-nitrogen bonds. These reactions are important in the synthesis of pharmaceuticals, agrochemicals, and dyes, where the formation of amines and amides is a key step. The compound’s versatility as a base and nucleophile makes it a useful tool for chemists designing complex molecules.

Furthermore, N,N-Dimethylbenzylamine finds application in the production of quaternary ammonium compounds, which are used as disinfectants, fabric softeners, and surfactants. Quaternization of N,N-Dimethylbenzylamine leads to the formation of these cationic surfactants, which play a critical role in industrial and household cleaning products. Its role in the formation of such compounds underscores its importance in consumer goods and industrial processes.

Due to its widespread use in various industries, N,N-Dimethylbenzylamine continues to be an important compound for research and development. Its role in catalysis, polymer production, and synthetic chemistry ensures its ongoing relevance in both academic and industrial settings.

References

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