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| | 1,4-Naphthoquinone Basic information |
| Product Name: | 1,4-Naphthoquinone | | Synonyms: | 1,4-Naftochinon;1,4-Naphthylquinone;ALPHA-NAPHTHOQUINONE;1,4-NAPHTHOQUINOLINE;1,4-NAPHTHOQUINONE;1,4-DIHYDRO-1,4-DIKETONAPHTHAL;1,4-DIHYDRO-1,4-DIKETONAPHTHALENE;-Naphthoquinone | | CAS: | 130-15-4 | | MF: | C10H6O2 | | MW: | 158.15 | | EINECS: | 204-977-6 | | Product Categories: | Pyridines;Is an important raw material in chemical, pharmaceutical, pesticide, plasticizer, spices, dye intermediates, as polymerization regulator of synthetic resin, rubber;Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;bc0001 | | Mol File: | 130-15-4.mol |  |
| | 1,4-Naphthoquinone Chemical Properties |
| Melting point | 119-122 °C(lit.) | | Boiling point | 243.22°C (rough estimate) | | density | 1,42 g/cm3 | | vapor pressure | <1 hPa (50 °C) | | refractive index | 1.5300 (estimate) | | Fp | 141 °C | | storage temp. | Store below +30°C. | | solubility | 0.09g/l | | form | Powder | | color | Khaki | | PH | 6.1 (10g/l, H2O, 20℃) | | Water Solubility | insoluble | | Merck | 14,6395 | | BRN | 878524 | | Stability: | Stable. Incompatible with strong reducing agents, strong oxidizing agents. | | InChIKey | FRASJONUBLZVQX-UHFFFAOYSA-N | | LogP | 1.71-1.77 at 25℃ | | CAS DataBase Reference | 130-15-4(CAS DataBase Reference) | | NIST Chemistry Reference | 1,4-Naphthalenedione(130-15-4) | | EPA Substance Registry System | 1,4-Naphthoquinone (130-15-4) |
| | 1,4-Naphthoquinone Usage And Synthesis |
| Chemical Properties | 1,4-Naphthoquinone is a yellow to greenish yellow crystalline solid that has pungent odor like benzoquinone. It is slightly soluble in water, soluble in ether, chloroform, benzene, glacial acetic acid. In alkaline solutions it produces a reddish-brown color. | | Uses | antibacterial, antineoplastic | | Uses | 1,4-Naphthoquinone is used as a strong dienophile in Diels-Alder reaction. It is also used as a precursor to anthroquinone and 5-nitro-1,4-naphthalenedione, which finds application in the preparation of aminoanthroquinone and is also used as a dye precursor. It is a basic component of Vitamin K. | | Definition | ChEBI: 1,4-naphthoquinone is the parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties. It derives from a hydride of a naphthalene. | | Synthesis Reference(s) | Synthesis, p. 330, 1977 DOI: 10.1055/s-1977-24385
Tetrahedron Letters, 31, p. 4871, 1990 DOI: 10.1016/S0040-4039(00)97755-4 | | General Description | Yellow needles or brownish green powder with an odor of benzoquinone. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | 1,4-Naphthoquinone may react with many acids and bases liberating heat and flammable gases (e.g., H2). The heat may be sufficient to start a fire in the unreacted portion of the ketone. May react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. May react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. | | Hazard | Irritant | | Health Hazard | ACUTE/CHRONIC HAZARDS: When heated to decomposition 1,4-Naphthoquinone emits toxic fumes and smoke. | | Fire Hazard | Flash point data for 1,4-Naphthoquinone are not available; however, 1,4-Naphthoquinone is probably combustible. | | Flammability and Explosibility | Notclassified | | Safety Profile | Poison by ingestion,
intravenous, subcutaneous, and
intraperitoneal routes. Experimental
reproductive effects. Questionable
carcinogen with experimental tumorigenic
data. When heated to decomposition it
emits acrid smoke and irritating fumes. | | Potential Exposure | 1,4-Naphthoquinone is used as a polymerization
regulator for rubber and polyester resins; in the
synthesis of dyes and pharmaceuticals; and as a fungicide
and algicide. | | Shipping | UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | | Purification Methods | Crystallise the quinone from diethyl ether (charcoal). It distils in steam. It also crystallises from *benzene or aqueous EtOH and sublimes in a vacuum. [Beilstein 7 IV 2422.] | | Incompatibilities | Ketones are incompatible with oxidizers
(chlorates, nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, epoxides, nitrated amines,
azo, diazo, azido compounds, carbamates, organic cyanates.
May react with many acids and bases liberating heat and
flammable gases (e.g., hydrogen) generating heat may be
sufficient to start a fire in the unreacted portion of the
ketone. May react with reducing agents such as hydrides,
alkali metals, and nitrides to produce flammable gas
(e.g., hydrogen) and heat. Incompatible with isocyanates,
aldehydes, cyanides, peroxides, and anhydrides. May react
violently with aldehydes. | | Waste Disposal | Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal. |
| | 1,4-Naphthoquinone Preparation Products And Raw materials |
| Raw materials | Chromium(VI) oxide-->Sodium dichromate dihydrate-->Potassium dichromate-->1-Naphthol | | Preparation Products | Sodium silicate-->NILE RED-->2,3-Dichloro-1,4-naphthoquinone-->Atovaquone-->3,3'-Dichlorobenzidine dihydrochloride-->2-Hydroxy-1,4-naphoquinone-->2,3-DIMETHYLANTHRAQUINONE-->2-Chloro-1,4-naphthoquinone-->1H-[1]-BENZAZEPHE-2,5(3H, 4H)-DIONE-->4-METHOXY-1-NAPHTHOL-->2-HYDROXYANTHRAQUINONE-->1,4-Dihydroxynaphthalene-->MFCD00666862-->1,4-Naphthalenedione, 2-chloro-3-[[4-(1,1-dimethylethyl)cyclohexyl]methyl]--->4-METHOXY-2-PHENYLAZO-1-NAPHTHOL |
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