1,8-Diaminonaphthalene
[CAS# 479-27-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: 1,8-Diaminonaphthalene
• Synonyms: 1,8-Naphthalenediamine
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.20
• CAS Registry Number: 479-27-6
• EC Number: 207-529-8
• SMILES: C1=CC2=C(C(=C1)N)C(=CC=C2)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 63-67 °C (Expl.)
• Index of Refraction: 1.757, Calc.^*
• Boiling Point: 352.1 °C (760 mmHg), Calc.^*, 387.1 °C (Expl.)
• Flash Point: 198.7±21.8 °C, Calc.^*, 195 °C (Expl.)
• Water solubility: slightly soluble

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H317-H351-H400-H410
• Safety Statements: P203-P261-P264-P270-P272-P273-P280-P301+P317-P302+P352-P318-P321-P330-P333+P317-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Germ cell mutagenicity	Muta.	2	H341
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

1,8-Diaminonaphthalene is an aromatic amine compound with the molecular formula C10H10N2. It consists of a naphthalene backbone with amino groups (-NH2) positioned at the 1 and 8 positions. This compound is a member of the naphthalene derivatives, and its discovery and applications have been well-documented in chemical literature.

The synthesis of 1,8-diaminonaphthalene was first reported in the mid-20th century, as part of efforts to explore the reactivity of aromatic amines and their derivatives. The compound was studied due to its potential to act as a precursor for various organic syntheses and its interesting chemical reactivity. As a diamine, 1,8-diaminonaphthalene can undergo a variety of reactions, including electrophilic substitution, which is common for aromatic compounds.

1,8-Diaminonaphthalene has found notable use in the synthesis of organic materials, particularly in the preparation of dyes and pigments. Its structure, with its two amino groups attached to a naphthalene ring, allows it to participate in the formation of azo dyes and other colored compounds. These dyes are widely used in the textile industry, as well as in the development of various pigments for inks and coatings. The ability to modify the reactivity and color properties of the compound makes it useful for these applications.

Additionally, 1,8-diaminonaphthalene has been employed in the preparation of polyamides and other polymeric materials. Polyamides are used in a range of industrial applications, from fibers for textiles to engineering plastics. The incorporation of 1,8-diaminonaphthalene into polymeric structures allows for the design of materials with specific properties, such as improved thermal stability, strength, or resistance to chemical degradation.

In the field of organic electronics, 1,8-diaminonaphthalene has been studied for its potential use in the development of semiconducting materials. Organic semiconductors, which are used in devices like organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), benefit from the presence of conjugated aromatic systems. The presence of amine groups in 1,8-diaminonaphthalene makes it a candidate for modifying the electronic properties of these materials, contributing to their conductivity or efficiency.

Furthermore, 1,8-diaminonaphthalene has also been explored in the context of chemical sensors, especially for detecting anions and small molecules. Its functional groups can interact with various chemical species, making it suitable for use in sensors designed to detect specific targets. These sensors find applications in environmental monitoring, industrial process control, and safety applications.

In conclusion, 1,8-diaminonaphthalene has broad applications in materials science, including in the synthesis of dyes, polymers, and organic semiconductors. Its ability to undergo a variety of chemical reactions and to participate in the design of functional materials has established it as a valuable compound in both industrial and research contexts.

References

1970. Heterocyclic analogs of pleiadiene. Chemistry of Heterocyclic Compounds, 6(1).
DOI: 10.1007/bf00475437

2021. The Molecular Diversity of 1,8-diaminonaphthalene in Organic Chemistry. Combinatorial Chemistry & High Throughput Screening, 24(10).
DOI: 10.2174/1386207323666201110144014

2023. 3D-printed layer-by-layer electrode graphene/poly(1,8-diaminonaphthalene) incorporated with silver nanoparticles as an electrochemical sensing platform for cefepime antibiotic determination. Colloid and Polymer Science, 301(9).
DOI: 10.1007/s00396-023-05126-w