N,N,N',N'-tetramethyl-1,3-Benzenediamine
[CAS# 22440-93-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N,N,N',N'-tetramethyl-1,3-Benzenediamine
• Synonyms: 1-N,1-N,3-N,3-N-tetramethylbenzene-1,3-diamine
• Molecular Formula: C₁₀H₁₆N₂
• Molecular Weight: 164.25
• CAS Registry Number: 22440-93-3
• EC Number: 244-998-8
• SMILES: CN(C)C1=CC(=CC=C1)N(C)C

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301-H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N,N,N',N'-Tetramethyl-1,3-benzenediamine is a chemical compound known for its distinctive structure and useful applications in organic chemistry. This compound features a benzene ring with two diamine groups where each nitrogen atom is substituted with a methyl group, resulting in a highly substituted diamine structure.

The discovery of N,N,N',N'-tetramethyl-1,3-benzenediamine is rooted in the search for effective reagents and intermediates in chemical synthesis. Its unique structure, with its multiple methyl groups, influences its reactivity and solubility, making it a valuable compound in various synthetic applications.

One of the primary applications of N,N,N',N'-tetramethyl-1,3-benzenediamine is as a stabilizer and reducing agent. It is utilized in the synthesis of various organic compounds, including dyes and polymers. Its role as a reducing agent is particularly important in the preparation of certain chemicals where controlled reduction is required.

In addition to its role in synthetic chemistry, this compound has applications in materials science. It is used as a precursor for the synthesis of specialty polymers and as a component in the development of materials with specific electronic or optical properties. Its ability to form complexes with various metals also makes it useful in the preparation of metal-organic frameworks and catalysts.

N,N,N',N'-Tetramethyl-1,3-benzenediamine is also studied for its potential applications in pharmaceuticals and agrochemicals. Its structural features may contribute to the development of new drug candidates or agricultural chemicals by modifying its reactivity or introducing it into new chemical environments.

Overall, N,N,N',N'-tetramethyl-1,3-benzenediamine is an important compound in organic and materials chemistry. Its versatility and unique structure make it a valuable tool for researchers working on a wide range of chemical synthesis and material development projects.

References

2022. Catalyst Engineering through Heterobidentate (N-X-Type) Ligand Design for Iridium-Catalyzed Borylation. *Synthesis*, 54(10).
DOI: 10.1055/a-1816-3334

2020. Preparation and microwave absorption properties of Ni/rGO/EP composite foam. *Journal of Materials Research*, 35(11).
DOI: 10.1557/jmr.2020.136

1968. Theoretical studies on the electronic spectra of substituted aromatic molecules. *Theoretical Chemistry Accounts*, 10(1).
DOI: 10.1007/bf00568789