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
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 8.06215
- Product name
- 1,4-Naphthoquinone
- Purity
- for synthesis
- Packaging
- 5G
- Price
- $41.6
- Updated
- 2024/03/01
- Product number
- 8.06215
- Product name
- 1,4-Naphthoquinone
- Purity
- for synthesis
- Packaging
- 250g
- Price
- $77.9
- Updated
- 2024/03/01
- Product number
- 8.06215
- Product name
- 1,4-Naphthoquinone
- Purity
- for synthesis
- Packaging
- 25kg
- Price
- $4240
- Updated
- 2024/03/01
- Product number
- 152757
- Product name
- 1,4-Naphthoquinone
- Purity
- 97%
- Packaging
- 5g
- Price
- $51.6
- Updated
- 2024/03/01
- Product number
- 152757
- Product name
- 1,4-Naphthoquinone
- Purity
- 97%
- Packaging
- 100g
- Price
- $52
- Updated
- 2024/03/01
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
Preparation Products
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View Lastest Price from 1,4-Naphthoquinone manufacturers
- 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
- 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
- Product
- 1,4-Naphthoquinone 130-15-4
- Price
- US $6.00/kg
- Min. Order
- 1kg
- Purity
- More than 99%
- Supply Ability
- 2000KG/Month
- Release date
- 2024-04-29