N-Methylbenzylamine
[CAS# 103-67-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polyamine
• Name: N-Methylbenzylamine
• Synonyms: N-Benzylmethylamine; N-Benzyl-N-methylamine
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• CAS Registry Number: 103-67-3
• EC Number: 203-133-4
• SMILES: CNCC1=CC=CC=C1

Properties

• Density: 0.939
• Melting point: -24 °C
• Boiling point: 184-189 °C
• Refractive index: 1.5214-1.5234
• Flash point: 77 °C
• Water solubility: 65 g/L (20 °C)

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 2735

Discovery and Applications

N-Methylbenzylamine is a significant compound in organic chemistry, featuring a benzyl group attached to a methylated amine. This simple structure gives rise to diverse reactivity, making it a valuable intermediate in various chemical processes.

The discovery of N-methylbenzylamine stems from the exploration of primary and secondary amines, which are widely used in both industrial and academic research. The introduction of a methyl group to the nitrogen atom in the amine structure modifies its basicity and reactivity, giving it distinct properties compared to its non-methylated counterpart, benzylamine. This small structural change significantly influences the compound’s chemical behavior.

In pharmaceutical chemistry, N-methylbenzylamine serves as an important building block for synthesizing active pharmaceutical ingredients. The amine group can readily undergo reactions such as alkylation, acylation, or reductive amination, making it a versatile reagent. Research has shown that derivatives of N-methylbenzylamine can exhibit various biological activities, including anti-inflammatory and antimicrobial properties. Its ability to form stable bonds with other chemical entities makes it a useful intermediate in drug discovery and development.

The compound also plays a role in materials science, where it is utilized in the synthesis of polymers and other advanced materials. N-methylbenzylamine’s reactivity allows for the formation of functionalized polymers that can be tailored for specific applications, such as coatings, adhesives, or electronic materials. Its structural stability and reactivity make it a valuable component in designing materials with desired properties.

Additionally, N-methylbenzylamine is frequently used in organic synthesis as a starting material or intermediate for the production of more complex molecules. Its straightforward structure and ability to participate in a wide range of chemical reactions enhance its utility in developing novel synthetic methodologies.

Overall, N-methylbenzylamine represents a valuable compound in chemical research with significant applications in pharmaceuticals, materials science, and organic synthesis.

References

2023. Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination. Science China Chemistry, 66(3).
DOI: 10.1007/s11426-022-1494-7

2024. Bioassays, characterization and electronic transitions studies of organtin(IV) dithiocarbamates of p-Bromo-N methylbenzylamine dithiocarbamates. Discover Chemistry, 1(1).
DOI: 10.1007/s44371-024-00063-1