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1,5-Diaminonaphthalene

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Identification
Molecular formula
C10H10N2
CAS number
2243-62-1
IUPAC name
naphthalene-1,5-diamine
State
State

At room temperature, 1,5-Diaminonaphthalene is typically a solid.

Melting point (Celsius)
140.00
Melting point (Kelvin)
413.15
Boiling point (Celsius)
401.20
Boiling point (Kelvin)
674.35
General information
Molecular weight
158.20g/mol
Molar mass
158.2020g/mol
Density
1.2570g/cm3
Appearence

1,5-Diaminonaphthalene appears as beige or light brown crystalline solid.

Comment on solubility

Solubility of Naphthalene-1,5-Diamine

Naphthalene-1,5-diamine, with its unique structure, exhibits specific solubility characteristics that are noteworthy for researchers and chemists. Solubility is fundamentally influenced by the chemical's structure and the nature of the solvent in which it is placed.

Key Points about Solubility:

  • Solvent Compatibility: Naphthalene-1,5-diamine is generally more soluble in organic solvents such as ethanol and acetone, but shows limited solubility in water.
  • Temperature Dependency: Its solubility may increase with temperature; thus, heating the solvent can enhance the dissolution of the compound.
  • Hydrophobic Nature: The large aromatic naphthalene groups contribute to its hydrophobic character, making it less favorable for polar solvents.

In summary, naphthalene-1,5-diamine showcases a classic example of how structural components affect solubility. As noted by scientists, *“The solubility of compounds is often linked to their molecular interactions with the solvent.”* Understanding these interactions is crucial for applications in synthesis and chemical processes.

Interesting facts

Interesting Facts about Naphthalene-1,5-Diamine

Naphthalene-1,5-diamine, often abbreviated as 1,5-DAN, is a fascinating organic compound that belongs to the family of aromatic amines. This compound is particularly significant in various areas of chemical research and industrial applications.

Key Properties and Applications

  • Stability and Reactivity: Naphthalene-1,5-diamine exhibits remarkable stability under a variety of conditions but can readily undergo reactions typical of amines.
  • Polymerization: This compound is extensively used as a precursor in the synthesis of polyamides and other polymers, contributing to the development of high-performance materials.
  • Dyes and Pigments: Naphthalene-1,5-diamine serves as an important building block in the manufacturing of synthetic dyes and pigments, making a significant impact on the textile and automotive industries.
  • Research Applications: In the realm of organic chemistry, 1,5-DAN is frequently utilized in studies of reaction mechanisms, photochemistry, and for the synthesis of complex organic compounds.

Chemical Behavior

This compound's unique structure—including its naphthalene moiety—allows for interesting reactivity, particularly in electrophilic substitutions. Due to the presence of two amine functional groups, naphthalene-1,5-diamine can act as a bifunctional reagent, enabling:

  • Cross-linking reactions that enhance polymer properties.
  • Complex formation with metal ions, which is relevant in coordination chemistry.

Trivia

As a compound derived from naphthalene, it shares a commonality with other aromatic compounds, including:

  • Environmental Impact: Being a member of the aromatic amine family, it has membrane-permeable properties that necessitate careful handling due to potential toxicity.
  • Historical Significance: Naphthalene and its derivatives have been utilized for centuries, beginning with their initial discovery and extraction from coal tar.

To encapsulate, naphthalene-1,5-diamine not only plays a pivotal role in various industrial applications but also represents an exciting domain of study for chemists, marrying the principles of organic synthesis with real-world application.

Synonyms
1,5-NAPHTHALENEDIAMINE
1,5-Diaminonaphthalene
2243-62-1
naphthalene-1,5-diamine
1,5-Naphthylenediamine
NCI-C03021
1,5-diamino naphthalene
13PD3J52LK
DTXSID3020916
CHEBI:53003
NSC-401110
NCGC00091284-03
1,5-Diaminonaphthalene (purified by sublimation)
1,5-Napthalenediamine
CCRIS 422
HSDB 4118
EINECS 218-817-8
MFCD00004029
NSC 401110
BRN 0907947
UNII-13PD3J52LK
1,5-DAN
1,5-naphthylendiamin
1,5-diaminonaphtalene
1,5-Naphthalene-di-amine
EC 218-817-8
naphthalene, 1,5-diamino-
WLN: L66J BZ GZ
SCHEMBL48843
4-13-00-00340 (Beilstein Handbook Reference)
DTXCID90916
1,5-Diaminonaphthalene, 97%
CHEMBL538965
Tox21_400040
BBL000009
NSC401110
STK370413
AKOS003617743
1,5-NAPHTHALENEDIAMINE [HSDB]
1,5-NAPHTHALENEDIAMINE [IARC]
AC-8269
CS-W013282
PS-5599
NCGC00091284-01
NCGC00091284-02
NCGC00091284-04
NCGC00091284-05
CAS-2243-62-1
DB-038118
D0101
D5689
NS00010628
C19463
EN300-202680
H11756
AB01332474-02
Q2191535
F0020-1999
1,5-Diaminonaphthalene, matrix substance for MALDI-MS, >=99.0% (HPLC)
InChI=1/C10H10N2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6H,11-12H