1,8-Bis(dimethylamino)naphtalene
[CAS# 20734-58-1]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Aromatic hydrocarbon
• Name: 1,8-Bis(dimethylamino)naphtalene
• Synonyms: N,N,N',N'-Tetramethyl-1,8-naphthalenediamine; N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine; Proton-sponge
• Molecular Formula: C₁₄H₁₈N₂
• Molecular Weight: 214.31
• CAS Registry Number: 20734-58-1
• EC Number: 244-001-6
• SMILES: CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 45 - 49 °C (Expl.)
• Boiling point: 304.4±22.0 °C 760 mmHg (Calc.)^*, 325.1 - 326.5 °C (Expl.)
• Flash point: 128.3±10.2 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.649 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,8-Bis(dimethylamino)naphthalene is an organic compound that belongs to the class of naphthalene derivatives, specifically substituted with two dimethylamino groups at positions 1 and 8 of the naphthalene ring system. The presence of two dimethylamino groups significantly influences the electronic properties of the molecule, making it an interesting candidate for various chemical applications.

The compound has been primarily utilized in the field of organic synthesis due to its unique structural characteristics. The naphthalene backbone, being aromatic, provides a stable platform for substitution, and the dimethylamino groups, being electron-donating groups, enhance the nucleophilicity of the molecule. This can make it more reactive in certain reactions, particularly those involving electrophilic aromatic substitution. The dimethylamino groups also increase the molecule’s solubility in polar solvents, which can be advantageous for some applications in both research and industry.

One significant application of 1,8-bis(dimethylamino)naphthalene is in the field of fluorescent dyes and sensors. The electron-rich nature of the dimethylamino groups, combined with the aromatic naphthalene core, can make the molecule a suitable candidate for fluorescence-based applications. The compound’s fluorescence properties can be influenced by the solvent environment, the presence of other functional groups, and the overall molecular structure. This makes it useful for fluorescence sensing in a variety of contexts, such as the detection of specific ions or molecules in biological or chemical environments.

In addition to its use in fluorescent sensors, 1,8-bis(dimethylamino)naphthalene has potential applications in the development of organic electronic materials. The electron-donating dimethylamino groups can interact with electronic components, potentially enhancing the compound's role as a charge-transport material in organic electronics. Such materials are integral in the development of devices like organic light-emitting diodes (OLEDs), organic photovoltaics, and organic field-effect transistors (OFETs). The compound’s electronic properties make it a potential candidate for incorporation into these technologies, especially where materials with high electron density are required.

The compound may also find applications in catalysis, particularly in reactions where electron-rich aromatic compounds act as ligands for metal catalysts. The dimethylamino groups could facilitate coordination with metal centers, making 1,8-bis(dimethylamino)naphthalene a potential ligand for various catalytic processes. In this regard, its use could be relevant in synthetic chemistry, especially in reactions that require the stabilization of metal intermediates or the activation of substrates in electrophilic aromatic substitution reactions.

Furthermore, due to its structural features, 1,8-bis(dimethylamino)naphthalene could be explored for its potential pharmacological activities. While the compound itself may not have been widely studied for medicinal purposes, derivatives of naphthalene with similar substitution patterns have been investigated for a range of biological activities, including antimicrobial, anticancer, and anti-inflammatory effects. The dimethylamino groups can influence the molecule's interaction with biological targets, potentially enhancing its ability to cross biological membranes and interact with specific receptors or enzymes.

In conclusion, 1,8-bis(dimethylamino)naphthalene is a versatile compound with potential applications in organic synthesis, fluorescence sensing, organic electronics, and catalysis. Its electron-donating dimethylamino groups and stable aromatic backbone make it an attractive candidate for a variety of chemical and technological applications. Although its biological and industrial applications are still under exploration, the compound shows promise as a building block for more complex molecules and materials with specific electronic or optical properties.

References

1974. Heterocyclic analogs of pleiadiene. Chemistry of Heterocyclic Compounds, 10(4).
DOI: 10.1007/bf00472432

2024. Molecular entanglement can strongly increase basicity. Communications Chemistry, 7(1).
DOI: 10.1038/s42004-024-01205-3

1975. Temperature-Jump Study of the Rates of Proton Transfer and the Strength of Intramolecular Hydrogen Bonds in Peri-Substituted Naphthalenes. Chemical and Biological Applications of Relaxation Spectrometry, 1.
DOI: 10.1007/978-94-010-1855-5_44