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1,2-NAPHTHOQUINONE

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1,2-NAPHTHOQUINONE Basic information

Product Name:
1,2-NAPHTHOQUINONE
Synonyms:
  • 1,2-dihydro-1,2-diketo-naphthalene
  • 1,2-Naftochinon
  • 1,2-Naphthaquinone
  • Dapoxetine Impurity S
  • o-Naphthoquinone
  • NAPHTHOQUINONE, 1,2-
  • BETA-NAPHTHOQUINONE
  • 1,2-NAPHTHALENEDIONE
CAS:
524-42-5
MF:
C10H6O2
MW:
158.15
EINECS:
208-360-2
Product Categories:
  • Anthraquinones, Hydroquinones and Quinones
  • Intermediates of Dyes and Pigments
  • Bioactive Small Molecules
  • Building Blocks
  • C10
  • Carbonyl Compounds
  • Cell Biology
  • Chemical Synthesis
  • Ketones
  • N
  • Organic Building Blocks
Mol File:
524-42-5.mol
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1,2-NAPHTHOQUINONE Chemical Properties

Melting point:
139-142 °C (dec.) (lit.)
Boiling point:
243.22°C (rough estimate)
Density 
1.450 g/cm3 (25℃)
refractive index 
1.5300 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), DMSO (Slightly)
form 
Crystalline Mass or Waxy Solid
color 
Colorless or white to pale yellow
Merck 
14,6394
BRN 
606546
Stability:
Light Sensitive
CAS DataBase Reference
524-42-5(CAS DataBase Reference)
EPA Substance Registry System
1,2-Naphthoquinone (524-42-5)
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Safety Information

Hazard Codes 
Xn,Xi,C,F
Risk Statements 
22-36/37/38-34-11-25
Safety Statements 
26-36-45-36/37/39-16-37/39-28A
RIDADR 
2811
WGK Germany 
3
RTECS 
QL7000000
Hazard Note 
Irritant
HS Code 
29146990
Hazardous Substances Data
524-42-5(Hazardous Substances Data)

MSDS

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1,2-NAPHTHOQUINONE Usage And Synthesis

Chemical Properties

brown powder

Uses

Chemical reagent and intermediate.

Uses

1,2-Naphthquinone is a highly reactive quinone species which aids in modulating cellular homeostasis and electrophilic signal transduction pathways.

Uses

1,2-Naphthoquinone was employed as mediator during electrochemical mapping of redox activity in normal human breast (MCF-10A) cells by scanning electrochemical microscopy (SECM).

Definition

ChEBI: 1,2-naphthoquinone is the parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles. It has a role as a carcinogenic agent and an aryl hydrocarbon receptor agonist. It derives from a hydride of a naphthalene.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 603, 1984 DOI: 10.1016/S0040-4039(00)99949-0
The Journal of Organic Chemistry, 51, p. 5390, 1986 DOI: 10.1021/jo00376a061

General Description

Golden yellow needles or brown powder. Decomposes to a bluish-black color on standing.

Air & Water Reactions

The neat chemical may be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

Ketones, such as 1,2-NAPHTHOQUINONE, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Hazard

Irritant

Health Hazard

ACUTE/CHRONIC HAZARDS: 1,2-NAPHTHOQUINONE is an irritant. When heated to decomposition it emits acrid smoke and fumes.

Fire Hazard

Flash point data for 1,2-NAPHTHOQUINONE are not available. 1,2-NAPHTHOQUINONE is probably combustible.

Purification Methods

Crystallise the quinone from ether (red needles) or *benzene (orange leaflets). [Beilstein 7 IV 2417.]

1,2-NAPHTHOQUINONE Preparation Products And Raw materials

Preparation Products

1,2-NAPHTHOQUINONESupplier

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