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130-15-4

Basic Information
CAS No.: 130-15-4
Name: 1,4-Naphthoquinone
Article Data: 386
Molecular Structure:
Molecular Structure of 130-15-4 (1,4-Naphthoquinone)
Formula: C10H6O2
Molecular Weight: 158.156
Synonyms: 1,4-Naphthoquinone(8CI);1,4-Dihydro-1,4-diketonaphthalene;NSC 113960;NSC9583;p-Naphthoquinone;a-Naphthoquinone;1,4-Naphthalenedione;
EINECS: 204-977-6
Density: 1.29 g/cm3
Melting Point: 119-122 °C(lit.)
Boiling Point: 297.935 °C at 760 mmHg
Flash Point: 111.219 °C
Solubility: Soluble in hot alcohol, ether, benzene, chloroform and carbon disulfide, insoluble in cold water, slightly soluble in petroleum ether
Appearance: Yellow needles or brownish green powder with an odor of benzoquinone
Hazard Symbols: VeryT+,DangerousN
Risk Codes: 25-26-36/37/38-43-50-34-11
Safety: 26-45-61-38-36/37/39-24-16
Transport Information: UN 2811 6.1/PG 1
PSA: 34.14000
LogP: 1.62180
Synthetic route
571-60-8

1,4-Dihydroxynaphthalene

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Heating;100%
With dihydrogen peroxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 50℃; for 1.5h;100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
91-20-3

naphthalene

A

85-44-9

phthalic anhydride

B

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 100%
B 0.05%
With oxygen at 340 - 360℃;A 100%
B 0.1%
With oxygen at 340 - 360℃;A 100%
B 0.02%
90-15-3

α-naphthol

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With Co(salN-Medpt); oxygen In acetonitrile for 0.5h;100%
With C126H112O32S6; oxygen In toluene for 1.33333h; Irradiation;100%
With K10 montmorillonite; iodic acid for 0.333333h; Heating;97%
10075-62-4

1,4-dimethoxynaphthalene

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With silver(II) oxide; nitric acid In acetone at 20℃;100%
With N-Bromosuccinimide; sulfuric acid In tetrahydrofuran; water at 20℃; for 0.25h;98%
With manganese(IV) oxide; nitric acid In dichloromethane for 1.5h; Ambient temperature;95%
84-85-5

4-methoxynaphth-1-ol

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;100%
With silica gel supported cerium(IV) ammonium nitrate-NaBrO3 In dichloromethane; water at 40℃; for 2h;95%
With Pyridine-2,6-dicarboxylic acid N-oxide; tert.-butylhydroperoxide; ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 11h;91%
106-51-4

p-benzoquinone

270589-03-2

(E,E)-2-pyridyldimethyl(buta-1,3-dienyl)silane

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 38h;100%
With hydrogenchloride In water at 20℃; for 38h; Product distribution; Further Variations:; Reagents; Solvents; Diels-Alder reaction;100%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

85-44-9

phthalic anhydride

B

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃;A 100%
B 0.01%
With oxygen at 340 - 360℃;A 100%
B 0.01%
With oxygen at 340 - 360℃;A 100%
B 0.01%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

C

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 0.01%
B 100%
C 0.02%
With oxygen at 340 - 360℃;A 0.03%
B 100%
C 0.05%
With oxygen at 340 - 360℃;A 0.01%
B 100%
C 0.01%
Reaxys ID: 11464679

Reaxys ID: 11464679

A

87-41-2

2-benzofuran-1(3H)-one

B

85-44-9

phthalic anhydride

C

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 354 - 357℃;A 0.2%
B 100%
C 0.15%
2243-61-0

1,4-diaminonaphthalene

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With sodium periodate In water; ethyl acetate at 20℃; for 0.25h;98%
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.166667h;90%
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    Product Name: 1,4-Naphthoquinone CAS: 130-15-4 MF: C10H6O2 MW: 158.15 EINECS: 204-977-6 Mol File: 130-15-4.mol 1,4-Naphthoquinone Structure 1,4-Naphthoquinone Chemical Properties Melting point 119-122 °C(lit.) Boiling poin

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1,4-Naphthoquinone is an organic compound with the formula C10H6O2, and its systematic name is the same with the product name. With the CAS registry number 130-15-4, it is also named as p-Naphthoquinone. Its EINECS number is 204-977-6. In addition, the molecular weight is 158.15. Its classification codes are: (1)Agricultural Chemical; (2)Drug / Therapeutic Agent; (3)Fungicide, bactericide, wood preservative; (4)Mutation data; (5)Reproductive Effect; (6)Tumor data. This chemical is used for the production of anthraquinone, and it is a kind of important agricultural fungicide.

Physical properties of 1,4-Naphthoquinone are: (1)ACD/LogP: 1.573; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.57; (4)ACD/LogD (pH 7.4): 1.57; (5)ACD/BCF (pH 5.5): 9.23; (6)ACD/BCF (pH 7.4): 9.23; (7)ACD/KOC (pH 5.5): 170.80; (8)ACD/KOC (pH 7.4): 170.80; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.617; (14)Molar Refractivity: 42.904 cm3; (15)Molar Volume: 122.551 cm3; (16)Polarizability: 17.008×10-24cm3; (17)Surface Tension: 52.92 dyne/cm; (18)Density: 1.29 g/cm3; (19)Flash Point: 111.219 °C; (20)Enthalpy of Vaporization: 53.782 kJ/mol; (21)Boiling Point: 297.935 °C at 760 mmHg; (22)Vapour Pressure: 0.001 mmHg at 25°C.

Preparation of 1,4-Naphthoquinone: this chemical can be prepared by 4-Amino-[1]naphthol. This reaction will need reagents NaOCl, Dowex 1X8-200 - chloride form and solvent 1,2-dimethoxy-ethane with the reaction time of 85 min. The yield is about 93%.

1,4-Naphthoquinone can be prepared by 4-Amino-[1]naphthol

Uses of 1,4-Naphthoquinone: it can be used to produce 2-(2'-acetylanilino)-1,4-naphthoquinone at the ambient temperature. It will need reagents CeCl3·7H2O, air and solvent ethanol with the reaction time of 24 hours. The yield is about 60%.

1,4-Naphthoquinone can be used to produce 2-(2'-acetylanilino)-1,4-naphthoquinone at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is irritating to eyes, respiratory system and skin, and it may cause sensitisation by skin contact, so you should avoid contact with skin. This substance is toxic if swallowed and is very toxic by inhalation. What's more, it is very toxic to aquatic organisms. It can cause burns. In case of insufficient ventilation, you need to wear suitable respiratory equipment. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible). You must avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\2c1c(cccc1)C(=O)/C=C/2
(2)Std. InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
(3)Std. InChIKey: FRASJONUBLZVQX-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 133mg/kg (133mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
guinea pig LD50 oral 400mg/kg (400mg/kg)   Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 37, 1966.
guinea pig LD50 oral 400mg/kg (400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 37, 1966.
mouse LD50 intraperitoneal 5500ug/kg (5.5mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 570, 1983.
mouse LDLo intravenous 10mg/kg (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 71, Pg. 210, 1941.
mouse LDLo oral 80mg/kg (80mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacology and Experimental Therapeutics. Vol. 71, Pg. 210, 1941.
mouse LDLo subcutaneous 40mg/kg (40mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 71, Pg. 210, 1941.
rat LD50 oral 190mg/kg (190mg/kg)   Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 37, 1966.
rat LD50 oral 190mg/kg (190mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 37, 1966.
rat LD50 subcutaneous 202mg/kg (202mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 16(5), Pg. 52, 1972.
rat LDLo intraperitoneal 50mg/kg (50mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 91, 1982.