| Identification | More | [Name]
1,4-Naphthoquinone | [CAS]
130-15-4 | [Synonyms]
1,4-DIHYDRO-1,4-DIKETONAPHTHAL
1,4-DIHYDRO-1,4-DIKETONAPHTHALENE
1,4-NAPHTHALENEDIONE
1,4-NAPHTHOQUINOLINE
1,4-NAPHTHOQUINONE
ALPHA-NAPHTHOQUINONE
A-NAPHTHOQUINONE
NAPHTHOQUINONE,1,4-
1,4-Naftochinon
1,4-Naphthaquinone
1,4-Naphthylquinone
Naphthoquinone
-Naphthoquinone
p-Naphthoquinone
Rcra waste number U166
rcrawastenumberu166
USAF cy-10
usafcy-10
1,4-naphthoquinone (alpha)
1,4-Napthoquinone | [EINECS(EC#)]
204-977-6 | [Molecular Formula]
C10H6O2 | [MDL Number]
MFCD00001676 | [Molecular Weight]
158.15 | [MOL File]
130-15-4.mol |
| Chemical Properties | Back Directory | [Appearance]
1,4-Naphthoquinone is a yellow to greenishyellow
crystalline solid. Pungent odor like benzoquinone. | [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℃) | [Stability:]
Stable. Incompatible with strong reducing agents, strong oxidizing agents. | [Water Solubility ]
insoluble | [Merck ]
14,6395 | [BRN ]
878524 | [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) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
130-15-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+,N,T,C,F | [Risk Statements ]
R25:Toxic if swallowed.
R26:Very Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
R50:Very Toxic to aquatic organisms.
R34:Causes burns.
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S24:Avoid contact with skin .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2811 6.1/PG 1
| [WGK Germany ]
3
| [RTECS ]
QL7175000
| [F ]
8 | [Hazard Note ]
Very Toxic | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
I | [HS Code ]
29146910 | [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. | [Hazardous Substances Data]
130-15-4(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 190 mg/kg LD50 dermal Rat 202 mg/kg |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [General Description]
Yellow needles or brownish green powder with an odor of benzoquinone. | [Reactivity Profile]
1,4-NAPHTHOQUINONE(130-15-4) 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. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Irritant | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits toxic fumes and smoke. | [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. | [Fire Hazard]
Flash point data for this compound are not available; however, 1,4-NAPHTHOQUINONE is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion,
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 48 hours after breathing overexposure, as pulmonary edema may be delayed. As
first aid for pulmonary edema, a doctor or authorized paramedic
may consider administering a drug or other inhalation
therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | [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. | [Chemical Properties]
1,4-Naphthoquinone is a yellow to greenishyellow
crystalline solid. Pungent odor like benzoquinone. | [Chemical Properties]
yellow to green powder | [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. | [Uses]
antibacterial, antineoplastic | [Application]
1,4-Naphthoquinone(130-15-4) is an important organic intermediate compound, it is the chemical intermediate of fungicide dichlone and dithianon, and also the by-product of anthraquinone synthesis. It can be used as polymerisation regulator of rubber and polyester resin, synthesis of dyestuffs and drugs, algaecide, corrosion inhibitor, stabiliser of transformer oil, etc.
| [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. | [Origin]
1,4-Naphthoquinone is a natural product that is widely distributed in nature and is found in black walnut and king walnut. Especially in several families of higher plants (like Plumbaginaceae, Juglandaceae, Ebenaceae, Boraginaceae, Dioncophyllaceae, Ancistrocladaceae, Iridaceae, Verbenaceae, Scrophulariaceae, Avicenniaceae, Balsaminaceae, Bignoniaceae, Gentianaceae, and Droseraceae), and in addition also being present in algae, fungi, some animals, and products of metabolism in some bacteria. | [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 | [Flammability and Explosibility]
Notclassified(100%) | [Synthesis]
1,4-Naphthoquinone(130-15-4) is prepared by reacting naphthalene with molecular oxygen in a gaseous phase in the presence of a catalyst containing vanadium.
Prior to reacting the naphthalene with oxygen, the catalyst is pre-treated with molecular oxygen at 300° to 400° C in the absence of organic compounds and immediately thereafter a gas mixture containing naphthalene and molecular oxygen is passed over the pretreated catalyst at temperatures in the range of 300° to 400° C. The catalyst pre-treatment can be carried out in the presence of water vapor and the subsequent reaction of naphthalene with molecular oxygen can also be carried out in the presence of water vapor.
| [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.] |
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