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1,4-Naphthoquinone

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Identification
Molecular formula
C10H6O2
CAS number
130-15-4
IUPAC name
naphthalene-1,4-dione
State
State

At room temperature, 1,4-Naphthoquinone is a solid.

Melting point (Celsius)
126.00
Melting point (Kelvin)
399.15
Boiling point (Celsius)
302.00
Boiling point (Kelvin)
575.15
General information
Molecular weight
158.15g/mol
Molar mass
158.1480g/mol
Density
1.4020g/cm3
Appearence

1,4-Naphthoquinone appears as yellow, crystalline solid. It has a distinctive odor and forms needle-like crystals. When exposed to air and light, it can slowly darken due to oxidation.

Comment on solubility

Solubility of Naphthalene-1,4-dione

Naphthalene-1,4-dione, commonly referred to as 1,4-naphthoquinone, is an intriguing compound with varying solubility characteristics. Here’s what you should know about its solubility:

  • Solvent Compatibility: Naphthalene-1,4-dione is primarily soluble in organic solvents. It exhibits good solubility in solvents such as dimethyl sulfoxide (DMSO) and ethanol.
  • Water Solubility: In contrast, naphthalene-1,4-dione shows limited water solubility. Its low polarity and molecular structure contribute to its poor interaction with water molecules.
  • Temperature Effects: As with many organic compounds, its solubility can increase with temperature, allowing for greater dissolution in suitable organic solvents as the temperature rises.
  • Applications of Solubility: The solubility characteristics of naphthalene-1,4-dione play a crucial role in its application in organic synthesis and in the formulation of dyes and pigments.

In summary, while naphthalene-1,4-dione is not highly soluble in water, its ability to dissolve in various organic solvents opens doors for numerous chemical reactions and applications. This dichotomy emphasizes the importance of understanding solubility in the handling and utilization of chemical compounds.

Interesting facts

Interesting Facts about Naphthalene-1,4-dione

Naphthalene-1,4-dione, also known as 1,4-naphthoquinone, is a fascinating compound that plays a significant role in both nature and synthetic chemistry. Here are some intriguing aspects of this compound:

  • Natural Sources: It is found in various plants, particularly in the resin of the Myrcia genus. Naphthalene-1,4-dione is responsible for some of the characteristic colors of certain flowers.
  • Biological Relevance: This compound is often acknowledged for its biological activity, particularly in the realm of photobiology, where it has been shown to influence plant growth and photosynthesis processes.
  • Industrial Applications: Naphthalene-1,4-dione is utilized in the synthesis of dyes, pharmaceuticals, and pesticides, showcasing its versatility in industrial applications.
  • Synthetic Pathways: There are several synthetic methods to obtain naphthalene-1,4-dione, with one of the most notable being the oxidation of naphthalene using agents such as potassium permanganate or chromic acid.
  • Research Advancements: Recent studies have explored its role in the development of organic electronic materials, including organic solar cells and light-emitting diodes, highlighting its potential in the field of renewable energy.

As a scientist or chemistry student, understanding naphthalene-1,4-dione offers insight into a compound that bridges the gap between organic chemistry, biological systems, and practical applications, thus emphasizing its importance in both academic and industrial settings.
Its unique properties and activities continue to inspire research and innovation across various scientific disciplines.

Synonyms
1,4-NAPHTHOQUINONE
130-15-4
naphthalene-1,4-dione
1,4-Naphthalenedione
NAPHTHOQUINONE
p-Naphthoquinone
alpha-Naphthoquinone
1,4-Naphthylquinone
a-naphthoquinone
USAF CY-10
1,4-Naftochinon
1,4-Dihydro-1,4-diketonaphthalene
RCRA waste number U166
1,4-dihydronaphthalene-1,4-dione
1,4-Naftochinon [Czech]
1,4-Naphthaquinone
NSC 9583
.alpha.-Naphthoquinone
CCRIS 5424
Naphthoquinone, 1,4-
HSDB 2037
UNII-RBF5ZU7R7K
Naphthoquinone 1
RBF5ZU7R7K
EINECS 204-977-6
DTXSID5040704
CHEBI:27418
AI3-24292
1,4-naphthalene-dione
NSC-9583
MFCD00001676
CHEMBL55934
NQ-1
DTXCID3020704
NSC9583
1,4-NAPHTHOQUINONE [MI]
1,4-NAPHTHOQUINONE [HSDB]
1,4 naphthoquinone
1,4-naphtho-quinone
RCRA waste no. U166
napthoquinone
pNaphthoquinone
naphthalene-1
Naphthoquinone #
1,4Naftochinon
1,4naphtaquinone
alphaNaphthoquinone
1,4-naphtoquinone
1,4Naphthylquinone
1,4naphthalenedione
1,4-diketonaphthalene
Dithianon metabolite NQ
Spectrum2_000481
Spectrum3_000754
Spectrum4_001245
1,4-naphtho-quinone, 3
WLN: L66 BV EVJ
SCHEMBL42139
1,4-Naphthoquinone, 97%
BSPBio_002368
KBioGR_001770
MLS000069814
SPBio_000341
1,4Dihydro1,4diketonaphthalene
BDBM24776
CHEBI:25481
KBio3_001588
1,4-Dihydro-1,4-naphthalenedione
Tox21_303967
CCG-39519
s9342
STL146359
AKOS004907201
AKOS025243281
CS-W016206
FN03395
FS-2704
HY-W015490
NCGC00164067-01
NCGC00164067-02
NCGC00357275-01
AC-34538
CAS-130-15-4
SMR000059173
DB-005069
N0040
NS00014590
EN300-21246
C02617
D70977
1,4-Naphthoquinone, purum, >=96.5% (HPLC)
Q161542
Z104494806
1,4-Naphthoquinone, 97% (dry wt.), cont. up to 5% water
204-977-6