2,3-Dichloro-1,4-naphthoquinone Property

Melting point:

194-197 °C (lit.)

Boiling point:

275 °C (2 mmHg)

Density 

1.4057 (rough estimate)

vapor pressure 

0Pa at 20℃

refractive index 

1.5410 (estimate)

Flash point:

275°C/2mm

storage temp. 

Store below +30°C.

form 

Fine Crystalline Powder

color 

Yellow

Water Solubility 

0.008 g/L

Merck 

14,3045

BRN 

1073511

LogP

2.9 at 23℃

CAS DataBase Reference

117-80-6(CAS DataBase Reference)

NIST Chemistry Reference

1,4-Naphthalenedione, 2,3-dichloro-(117-80-6)

EPA Substance Registry System

Dichlone (117-80-6)

Safety

Hazard Codes 

Xn,N

Risk Statements 

22-36/38-50/53

Safety Statements 

26-60-61

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

QL7525000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29147090

Hazardous Substances Data

117-80-6(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1300 mg/kg (Bailey, White)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2,3-Dichloro-1,4-naphthoquinone Chemical Properties,Usage,Production

Chemical Properties

YELLOW FINE CRYSTALLINE POWDER

Uses

Fungicide used on fruits, field crops and vegetables

Uses

Use in textiles, as organic catalyst, as chemical intermediate, as additive in dye binders. Also used as an important catalyst to produce 3,3-dichlorobenzene.

Uses

Fungicide for agriculture and textiles; herbicide.

General Description

2,3-Dichloro-1,4-naphthoquinone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,3-Dichloro-1,4-naphthoquinone is a halogenated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Health Hazard

INHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression.

Fire Hazard

Special Hazards of Combustion Products: Highly toxic fumes are imminent.

Flammability and Explosibility

Not classified

Agricultural Uses

Fungicide: Not currently registered in the U.S. Not approved for use in the EU. Dichlone is used as a fungicide for foliage and to control blue algae in ponds, swimming pools and lakes. As a substitute for copper and sulfur to control rot on fruit trees, vegetables, field crops, ornamentals, resident and commercial outdoor areas.

Trade name

ALGISTAT®; COMPOUND 604®; PHYGON®; PHYGON® PASTE; PHYGON® SEED PROTECTANT; PHYGON® XL; QUINTAR®; QUINTAR® 540F; SANQUINON®; UNIROYAL® 604; USR® 604; U.S. RUBBER® 604

Safety Profile

Poison by ingestion and intraperitoneal routes. Mildly toxic by skin contact. A skin, eye, and mucous membrane irritant. Large doses can cause central nervous system depression. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. A fungcide and algicide. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.

Environmental Fate

Plant. In plants, dichlone loses both chlorine atoms and are replaced by sulphydryl groups to give a substituted dimercapto compound (Hartley and Kidd, 1987).
Photolytic. The UV absorption band for dichlone is 330 nm (Gore et al., 1971). Irradiation of dichlone in a variety of organic solvents (benzene, isopropanol, ethanol) using UV light produced a number of dehalogenated compounds. In the absence or presence of oxygen, 2-chloro-1,4-naphthoquinone, 1,4-naphthoquinone and 1,4-naphthalenediol were produced. Further irradiation in the presence of oxygen yielded phthalic acid and phthalic anhydride as the major products. In a mixture of benzene and isopropanol, dichlone degraded to the minor products: 2-chloro-3-hydroxy-1,4-naphthoquinone, 2- chloro-3-phenoxy-1,4-naphthoquinone, 2,3-dichloro-4-hydroxy-1-keto-2-phenyl-1,2- dihydronaphthalene and isopropyl-1-chloro-2,3-dioxo-1-indanecarboxylate (Ide et al., 1979).
Chemical/Physical. Emits toxic fumes of chlorine when heated to decomposition (Sax and Lewis, 1987).

Purification Methods

Crystallise the quinone from EtOH. [Beilstein 7 IV 2426.]