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1,4-Naphthoquinone

1,4-Naphthoquinone Structure
CAS No.
130-15-4
Chemical Name:
1,4-Naphthoquinone
Synonyms
Naphthalene-1,4-dione;Naphthoquinone;1,4-NAPHTHALENEDIONE;1,4-Naphthaquinone;A-NAPHTHOQUINONE;4-Naphthoquinone;α-Naphthoquinone;1,4-naphtoquinone;usafcy-10;USAF cy-10
CBNumber:
CB7381254
Molecular Formula:
C10H6O2
Molecular Weight:
158.15
MOL File:
130-15-4.mol
MSDS File:
SDS
Modify Date:
2024/7/9 21:58:15

1,4-Naphthoquinone 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)
Flash point 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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS05,GHS06,GHS09
Signal word  Danger
Hazard statements  H301+H311-H314-H317-H330-H335-H410
Precautionary statements  P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes  T+,N,T,C,F
Risk Statements  25-26-36/37/38-43-50-34-11
Safety Statements  26-36/37-45-61-38-36/37/39-28A-24-16
RIDADR  UN 2811 6.1/PG 1
WGK Germany  3
RTECS  QL7175000
8
Hazard Note  Very Toxic
TSCA  Yes
HazardClass  6.1
PackingGroup  I
HS Code  29146910
Toxicity LD50 orally in Rabbit: 190 mg/kg LD50 dermal Rat 202 mg/kg
NFPA 704
1
4 0

1,4-Naphthoquinone price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.06215 1,4-Naphthoquinone for synthesis 130-15-4 5G ₹2420.01 2022-06-14 Buy
Sigma-Aldrich(India) 8.06215 1,4-Naphthoquinone for synthesis 130-15-4 250G ₹7050 2022-06-14 Buy
Sigma-Aldrich(India) 8.06215 1,4-Naphthoquinone for synthesis 130-15-4 1KG ₹22740 2022-06-14 Buy
Sigma-Aldrich(India) 8.06215 1,4-Naphthoquinone for synthesis 130-15-4 25KG ₹312070 2022-06-14 Buy
Sigma-Aldrich(India) 70372 1,4-Naphthoquinone purum, ≥96.5% (HPLC) 130-15-4 50G ₹3388.23 2022-06-14 Buy
Product number Packaging Price Buy
8.06215 5G ₹2420.01 Buy
8.06215 250G ₹7050 Buy
8.06215 1KG ₹22740 Buy
8.06215 25KG ₹312070 Buy
70372 50G ₹3388.23 Buy

1,4-Naphthoquinone Chemical Properties,Uses,Production

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

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.

Application

1,4-Naphthoquinone 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.

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.

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.

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.

Synthesis

1,4-Naphthoquinone 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.

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.

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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 p-Naphthoquinone Rcra waste number U166 rcrawastenumberu166 USAF cy-10 usafcy-10 1,4-Naphthochi 1,4-Naphthoquinone purum, >=96.5% (HPLC) 1,4-Naphthoquinone, 97% dry weight, contains up to 5% water 1,4-naphthoquinone anion radical 1,4-Naphthochinone α-Naphthoquinone 1,4-Naphthalenedione NAPHTHOQUINONE,1,4- 1,4-Napthoquinone 1,4-Naphthoquinone, Standard 1,4-DIOXONAPHTHALENE 1,4-Naphthoquinone, contains up to 6% water, 99% 1,4-Naphthoquinone 97% NAPTHOQUINONE,1,4-(RG) PARA-NAPHTHOQUINONE 1,4-Naphthochinon 1,4-Naphthoquinone, 97+% (dry wt.), cont. up to 5% water 1,4-naphthoquinone (alpha) 1,4-Dihydronaphthalene-1,4-dione 1,4-Naphthoquinone (dry wt.), cont. up to 5% water NAPHTHOQUINONE,1,4-(RG) 1,4-Naphthoquinone ,95% 1,4-Naphthoquinone,α-Naphthoquinone 1.4-Naphthoquinone 1g [130-15-4] Naphthalene-1,4-dione 97% 1,4 napthaquinone 1,4-Naphthoquinone, contains up to 6% water, 99% 100GR 1,4-Naphthoquinone, contains up to 6% water, 99% 500GR 1,4-NAPHTHOQUINONE FOR SYNTHESIS 1,4-Naphthoquinone,99%,contains up to 6% water Dapoxetine Impurity R нафтахинон, нафталин-1,4-дион, α-Naphthoquinone, п-нафтахинон, 1,4-Naphthoquinone, Naphthalene-1,4-dion 1,4-napthaquinone,Naphthoquinone 1,4-Naphthoquinone> 1,4-Naphthoquinone @100 μg/mL in Dichloromethane 1,4-NaphthoquinoneSolution,1,000mg/L,1ml 1,4-Naphthoquinone,>98% 1,4-Naphthoquinone ISO 9001:2015 REACH 4-Di-hydroxyphenyl)-ethanol 4-dihydroxyphenylethanol 1,4-Naphthaquinone 1,4-naphtoquinone A-NAPHTHOQUINONE 1,4-NAPHTHALENEDIONE Naphthoquinone Naphthalene-1,4-dione