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2-Hydroxy-1,4-naphoquinone

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Name

2-Hydroxy-1,4-naphoquinone

EINECS 201-496-3
CAS No. 83-72-7 Density 1.482 g/cm3
PSA 54.37000 LogP 1.50750
Solubility 2 g/L (20 °C) in water Melting Point 192-195 °C (dec.)(lit.)
Formula C10H6O3 Boiling Point 339.908 °C at 760 mmHg
Molecular Weight 174.156 Flash Point 173.572 °C
Transport Information N/A Appearance Yellow crystal powder
Safety 26-37/39-36/37/39-36 Risk Codes 36/37/38-68-36-22
Molecular Structure Molecular Structure of 83-72-7 (2-Hydroxy-1,4-naphoquinone) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

1,4-Naphthoquinone,2-hydroxy- (6CI,8CI);1,4-Dihydro-1,4-dioxo-2-hydroxynaphthalene;2-Hydroxy-1,4-naphthalenedione;2-Hydroxy-1,4-naphthoquinone;2-Hydroxynaphthoquinone;C.I. 75480;C.I. Natural Orange 6;Flower of Paradise;Henna;Henna (dye);Lawsone;Mehendi;Mendi;NSC 27285;NSC 52500;NSC 8625;Pakarli;Q 0;

Article Data 152

2-Hydroxy-1,4-naphoquinone Synthetic route

35135-38-7

2-hydroxy-3-iodonaphthalene-1,4-dione

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogen iodide In dichloromethane at 20℃;100%
110-91-8

morpholine

521-24-4

sodium 1,2-naphthoquinone-4-sulfonate

A

83-72-7

2-Hydroxy-1,4-naphthoquinone

B

4569-83-9

4-morpholinonaphthalene-1,2-dione

C

disodium 2-hydroxy-1-oxo-1,4-dihydro-4,4-naphthalenedisulfonate

Conditions
ConditionsYield
pH=8;A n/a
B 99%
C n/a
1785-67-7

1,2,4-triacetyloxynaphthalene

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
Stage #1: 1,2,4-triacetyloxynaphthalene With hydrogenchloride In methanol; water at 70℃; for 1h;
Stage #2: With dihydrogen peroxide In water at 20℃;
91.6%
Stage #1: 1,2,4-triacetyloxynaphthalene With hydrogenchloride In methanol; water for 1h; Reflux;
Stage #2: With dihydrogen peroxide In methanol; water
91.6%
With sodium hydroxide; air
2348-82-5

2-methoxy-1,4-naphthoquinone

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 40℃; for 3h;91%
With aluminum (III) chloride; dichloromethane at -5 - 40℃; for 3h;87.1%

2-(N-phenylsulfinamoyl)-1,4-naphthoquinone

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;90%
74097-20-4

2-hydroxy-1,4-dimethoxynaphthalene

A

83-72-7

2-Hydroxy-1,4-naphthoquinone

B

18916-57-9

4-methoxy-1,2-naphthoquinone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; water In acetonitrile Yield given;A n/a
B 87%
With ammonium cerium(IV) nitrate; water In acetonitrile Yields of byproduct given;A n/a
B 87%

2--1,4-naphthoquinone

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;86%
159495-45-1

methyl 1,4-dihydro-1,4-dioxo-3-(1-pyrrolidinyl)-2-naphthoate

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 100℃; for 5h;83.3%
574-00-5

1,2-Dihydroxynaphthalene

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With KO2 In pyridine; toluene at -10℃; for 6h;80%
With KO2 In pyridine; toluene at -10℃; for 6h; Mechanism; oxidation of other dihydroxynaphthalenes in heterogeneous aprotic media;80%
With crown-ether In pyridine; toluene for 0.0833333h;60%
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;56%
With alkaline solution; oxygen
132-86-5

1,3-dihydroxynaphthalene

83-72-7

2-Hydroxy-1,4-naphthoquinone

Conditions
ConditionsYield
With zirconium phosphate; phthalocyanine[Fe(3+)]; oxygen In acetone at 20℃; for 6h;80%
With oxygen In 1,4-dioxane; water at 20℃; for 6h;79%
With crown-ether In pyridine; toluene for 0.0833333h;60%

2-Hydroxy-1,4-naphoquinone Chemical Properties

The chemical name of 2-HYDROXYNAPHTHOQUINONE(83-72-7) is 2-Hydroxy-1,4-naphoquinone and the IUPAC name is 4-hydroxynaphthalene-1,2-dione.its molecular formula is C10H6O3,with the formula weight of 174.15g/mol.
CAS No.: 83-72-7
EINECS: 201-496-3
RTECS: QL8200000
RTECS Class: Drug; Mutagen
Appearance: Yellow crystal powder
Structure:
                      
The chemical synonymous of 2-HYDROXYNAPHTHOQUINONE(83-72-7) are 1,4-Naphthalenedione,2-hydroxy-;1,4-Naphthoquinone, 2-hydroxy-;2-Hydroxy-1,4-naphthalenedione;2-hydroxy-4-naphthalenedione;2-hydroxy-4-naphthoquinone;2-Hydroxynaphthoquinone;4-Naphthalenedione,2-hydroxy-1
The density of  2-HYDROXYNAPHTHOQUINONE(83-72-7) is 1.481 g/cm3 and it has a melting point of 192-195 °C (dec.)(lit.).The boiling point is 352.4 °C at 760 mmHg ,and its flash point is 181.1 °C .The water solubility should be equal to 2 g/L (20 oC).and with the nature of stable、combustible、incompatible with strong oxidizing agents.

2-Hydroxy-1,4-naphoquinone Uses

2-HYDROXYNAPHTHOQUINONE(83-72-7) is used in hair dyes, fungicides

2-Hydroxy-1,4-naphoquinone Production

Product Categories: Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones

2-Hydroxy-1,4-naphoquinone Toxicity Data With Reference

1.   

mma-sat 33 µg/plate

   ENMUDM    Environmental Mutagenesis. 8 (Suppl 7)(1986),1.
2.   

ipr-mus LD50:100 mg/kg

   JMCMAR    Journal of Medicinal Chemistry. 26 (1983),570.

 

2-Hydroxy-1,4-naphoquinone Consensus Reports

Reported in EPA TSCA Inventory.

2-Hydroxy-1,4-naphoquinone Safety Profile

Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes:
    Xn: Harmful 
    Xi: Irritant 
Risk Statements about 2-HYDROXYNAPHTHOQUINONE(83-72-7):
    R22 Harmful if swallowed.
    R36 Irritating to eyes.
    R68 Possible risk of irreversible effects.
    R36/37/38 Irritating to eyes, respiratory system and skin.   
Safety Statements about 2-HYDROXYNAPHTHOQUINONE(83-72-7):
    S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical
advice.
    S36 Wear suitable protective clothing.
    S37/39 Wear suitable gloves and eye/face protection.
    S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.

2-Hydroxy-1,4-naphoquinone Specification

Storage:Keep tightly closed. Store in a cool dry place. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling:Avoid ingestion and inhalation. Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.

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