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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
1,2-NAPHTHOQUINONE Structure
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
InChIInChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
InChIKeyKETQAJRQOHHATG-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=CC=C2)C=CC1=O
CAS DataBase Reference524-42-5(CAS DataBase Reference)
EPA Substance Registry System1,2-Naphthoquinone (524-42-5)
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
TSCA TSCA listed
HS Code 29146990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazardous Substances Data524-42-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
1,2-NAPHTHOQUINONE Usage And Synthesis
Chemical Propertiesbrown powder
UsesChemical reagent and intermediate.
Uses1,2-Naphthquinone is a highly reactive quinone species which aids in modulating cellular homeostasis and electrophilic signal transduction pathways.
Uses1,2-Naphthoquinone was employed as mediator during electrochemical mapping of redox activity in normal human breast (MCF-10A) cells by scanning electrochemical microscopy (SECM).
DefinitionChEBI: 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 DescriptionGolden yellow needles or brown powder. Decomposes to a bluish-black color on standing.
Air & Water ReactionsThe neat chemical may be sensitive to prolonged exposure to air and light. Insoluble in water.
Reactivity ProfileKetones, 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.
HazardIrritant
Health HazardACUTE/CHRONIC HAZARDS: 1,2-NAPHTHOQUINONE is an irritant. When heated to decomposition it emits acrid smoke and fumes.
Fire HazardFlash point data for 1,2-NAPHTHOQUINONE are not available. 1,2-NAPHTHOQUINONE is probably combustible.
Purification MethodsCrystallise the quinone from ether (red needles) or *benzene (orange leaflets). [Beilstein 7 IV 2417.]
Tag:1,2-NAPHTHOQUINONE(524-42-5) Related Product Information
4-Chloro-1,2-naphthalenedione 1,2-Naphthoquinone-4-sulfoni POTASSIUM 1,2-NAPHTHOQUINONE-4-SULFONIC ACID DIHYDROTANSHINONE 1,2-NAPHTHOQUINONE Cryptotanshinone 1,4-Naphthoquinone, 2,3-dichloro-,2,3-Dichloro-1,4-naphthoquinone (dichlone),2,3-dichloro-4-naphthoquinon 1,4-dihydroxynaphthalene,1:1mixturewith1,4-naphthoquinon Menadione 1,4-Naphthoquinone, 2-hydroxy-,2-hydroxy-4-naphthoquinon 1,2-NAPHTHOQUINONE-2-DIAZIDO-4-SULFONYL CHLORIDE 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-,2-hydroxy-3-(3-methyl-2-butenyl)-4-naphthoquinon 5,12-NAPHTHACENEQUINONE SODIUM 1,2-NAPHTHOQUINONE-2-DIAZIDO-5-SULFONATE 4,8-diamino-2-bromo-1,5-naphthoquinone Menlaquinone 9 2,3,4,4'-Tetrahydroxybenzophenone 1,2-naphthoquinonediazido-5-sulfonate 1 3-BIS(2 6-DIISOPROPYLPHENYL)IMIDAZOL-&

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