- Product Name:
- U.s. rubber 604
- USR 604
- Product Categories:
- Building Blocks
- Carbonyl Compounds
- Chemical Synthesis
- Organic Building Blocks
- Intermediates of Dyes and Pigments
- Mol File:
2,3-Dichloro-1,4-naphthoquinone Chemical Properties
- Melting point:
- 194-197 °C (lit.)
- Boiling point:
- 275 °C (2 mmHg)
- 1.4057 (rough estimate)
- refractive index
- 1.5410 (estimate)
- Flash point:
- storage temp.
- Store below +30°C.
- Fine Crystalline Powder
- Water Solubility
- 0.008 g/L
- 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)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 2811 6.1/PG 3
- WGK Germany
- HS Code
- Hazardous Substances Data
- 117-80-6(Hazardous Substances Data)
- LD50 orally in rats: 1300 mg/kg (Bailey, White)
2,3-Dichloro-1,4-naphthoquinone Usage And Synthesis
YELLOW FINE CRYSTALLINE POWDER
Fungicide for agriculture and textiles; herbicide.
Fungicide used on fruits, field crops and vegetables
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.
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.
INHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression.
Special Hazards of Combustion Products: Highly toxic fumes are imminent.
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.
ALGISTAT®; COMPOUND 604®; PHYGON®; PHYGON® PASTE; PHYGON® SEED PROTECTANT; PHYGON® XL; QUINTAR®; QUINTAR® 540F; SANQUINON®; UNIROYAL® 604; USR® 604; U.S. RUBBER® 604
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.
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).
Crystallise the quinone from EtOH. [Beilstein 7 IV 2426.]
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