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| | 2,3-Dichloro-1,4-naphthoquinone Basic information |
| | 2,3-Dichloro-1,4-naphthoquinone Chemical Properties |
| 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) | | Fp | 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 | | InChI | 1S/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H | | InChIKey | SVPKNMBRVBMTLB-UHFFFAOYSA-N | | SMILES | ClC1=C(Cl)C(=O)c2ccccc2C1=O | | 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) |
| 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 | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29147090 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Skin Irrit. 2 | | Hazardous Substances Data | 117-80-6(Hazardous Substances Data) | | Toxicity | LD50 orally in rats: 1300 mg/kg (Bailey, White) |
| | 2,3-Dichloro-1,4-naphthoquinone Usage And Synthesis |
| Chemical Properties | YELLOW FINE CRYSTALLINE POWDER | | Uses | Fungicide for agriculture and textiles; herbicide. | | 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. | | 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.] |
| | 2,3-Dichloro-1,4-naphthoquinone Preparation Products And Raw materials |
| Raw materials | Bromine-->FUMING SULFURIC ACID-->Iron-->Ferric chloride-->1,3-Dinitrobenzene-->Naphthionic acid-->1,4-Naphthoquinone-->1,4-Naphthalenedione,2,3-dichloro-2,3-dihydro--->9,10-DiMethoxyanthracene-->2-Chloro-1,4-naphthoquinone | | Preparation Products | 2-(2H-Benzotriazol-2-yl)-4,6-ditertpentylphenol-->1 4-DIBUTOXY-2 3-NAPHTHALENEDI--->1-AMINO-2-METHYLANTHRAQUINONE-->UV-320-->[1,2]benzisothiazolo[2,3,4-lma]benzo[h]quinoxalino[2,3-c]carbazole-11,16-dione 9,9-dioxide-->3-Benzoyl-2-phenylnaphtho[2,3-b]furan-4,9-dione |
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