ChemicalBook > CAS DataBase List > 1,4-Naphthoquinone

1,4-Naphthoquinone

Product Name
1,4-Naphthoquinone
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
Formula Weight
158.15
MOL File
130-15-4.mol
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1,4-Naphthoquinone Property

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)
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Safety

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
F 
8
Hazard Note 
Very Toxic
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
I
HS Code 
29146910
Hazardous Substances Data
130-15-4(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 190 mg/kg LD50 dermal Rat 202 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H330Fatal if inhaled

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.06215
Product name
1,4-Naphthoquinone
Purity
for synthesis
Packaging
5G
Price
$41.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.06215
Product name
1,4-Naphthoquinone
Purity
for synthesis
Packaging
250g
Price
$77.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.06215
Product name
1,4-Naphthoquinone
Purity
for synthesis
Packaging
25kg
Price
$4240
Updated
2024/03/01
Sigma-Aldrich
Product number
152757
Product name
1,4-Naphthoquinone
Purity
97%
Packaging
5g
Price
$51.6
Updated
2024/03/01
Sigma-Aldrich
Product number
152757
Product name
1,4-Naphthoquinone
Purity
97%
Packaging
100g
Price
$52
Updated
2024/03/01
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1,4-Naphthoquinone Chemical Properties,Usage,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.

Uses

antibacterial, antineoplastic

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.

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

Not classified

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.

1,4-Naphthoquinone Preparation Products And Raw materials

Raw materials

1-Naphthol Sodium dichromate dihydrate Chromium(VI) oxide Potassium dichromate

Preparation Products

Nile Red 2-Hydroxy-1,4-naphoquinone 2,3-Dichloro-1,4-naphthoquinone Atovaquone Sodium silicate 2,3-DIMETHYLANTHRAQUINONE 3,3'-Dichlorobenzidine dihydrochloride
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Americas 1 Belgium 2 Canada 2 China 346 Europe 5 France 2 Germany 8 India 24 Italy 1 Japan 7 Russia 1 Slovakia 1 South Korea 1 Sweden 1 Switzerland 3 Ukraine 2 United Kingdom 19 United States 53 Global 479
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View Lastest Price from 1,4-Naphthoquinone manufacturers

HebeiShuoshengImportandExportco.,Ltd
Product
1,4-Naphthoquinone 130-15-4
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-08
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
1,4-Naphthoquinone 130-15-4
Price
US $50.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-05-20
Hebei Weibang Biotechnology Co., Ltd
Product
1,4-Naphthoquinone 130-15-4
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-21

130-15-4, 1,4-NaphthoquinoneRelated Search:

2-methyl-5-hydroxy-1,4-naphthoquinon 5-Hydroxy-1,4-naphthalenedione VITAMIN K1 2-CHLORO-3-(4-MORPHOLINO)-1,4-NAPHTHOQUINONE 1,4-CHRYSENEQUINONE 2-hydroxy-3-methyl-1,4-naphthoquinone 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-,2-hydroxy-3-(3-methyl-2-butenyl)-4-naphthoquinon 1,4-Naphthoquinone, 5,8-dihydroxy-,,8-Dihydroxy-[1,4]naphthoquinone,5,8-dihydroxy-4-naphthoquinon 1,4-Naphthoquinone, 2,3-dichloro-,2,3-Dichloro-1,4-naphthoquinone (dichlone),2,3-dichloro-4-naphthoquinon 2,3-dihydro-2-methyl-1,4-naphthoquinone-2-sulfonatesodiu Menadione 1,4-Naphthoquinone, 2-chloro-,2-chloro-4-naphthoquinon 1,4-ANTHRAQUINONE parvaquone 1,4-Naphthoquinone, 2-Amino-3-chloro-,3-Chloro-2-amino-1,4-naphthoquinone,2-amino-3-chloro-4-naphthoquinon Shikalkin Menaquinone 6 1,4-naphthoquinone,2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetrae

  • 1,4-Naftochinon
  • 1,4-Naphthaquinone
  • 1,4-Naphthylquinone
  • 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-naphtoquinone
  • A-NAPHTHOQUINONE
  • ALPHA-NAPHTHOQUINONE
  • 1,4-NAPHTHOQUINOLINE
  • 1,4-NAPHTHOQUINONE
  • 1,4-NAPHTHALENEDIONE
  • 1,4-DIHYDRO-1,4-DIKETONAPHTHAL
  • 1,4-DIHYDRO-1,4-DIKETONAPHTHALENE
  • Naphthoquinone
  • -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
  • Naphthalene-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]
  • 4-Naphthoquinone
  • 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
  • 1,4-Naphthoquinone&gt
  • 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
  • α-Naphthoquinone