2,3-Dichloro-1,4-naphthoquinone

2,3-Dichloro-1,4-naphthoquinone Basic information
Product Name:2,3-Dichloro-1,4-naphthoquinone
Synonyms:Quintar;Quintar 540F;dichlone (bsi,iso,jmaf);2,3-Dichloro-1,4-naphthoquinone, Dichlon;Dichlone【pesticide】;2,3-Dichloro-1,4-naphthoquinone,98%;2,3-DICHLORO-1,4-NAPHTHOQUINONE, 98.5%;dichlone (ISO) 2,3-dichloro-1,4-naphthoquinone
CAS:117-80-6
MF:C10H4Cl2O2
MW:227.04
EINECS:204-210-5
Product Categories:Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Intermediates of Dyes and Pigments
Mol File:117-80-6.mol
2,3-Dichloro-1,4-naphthoquinone Structure
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
LogP2.9 at 23℃
CAS DataBase Reference117-80-6(CAS DataBase Reference)
NIST Chemistry Reference1,4-Naphthalenedione, 2,3-dichloro-(117-80-6)
EPA Substance Registry SystemDichlone (117-80-6)
Safety Information
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 Data117-80-6(Hazardous Substances Data)
ToxicityLD50 orally in rats: 1300 mg/kg (Bailey, White)
MSDS Information
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2,3-Dichloro-1,4-naphthoquinone English
SigmaAldrich English
ACROS English
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2,3-Dichloro-1,4-naphthoquinone Usage And Synthesis
Chemical PropertiesYELLOW FINE CRYSTALLINE POWDER
UsesUse in textiles, as organic catalyst, as chemical intermediate, as additive in dye binders. Also used as an important catalyst to produce 3,3-dichlorobenzene.
UsesFungicide used on fruits, field crops and vegetables
UsesFungicide for agriculture and textiles; herbicide.
General Description2,3-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 ReactionsInsoluble in water.
Reactivity Profile2,3-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 HazardINHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression.
Fire HazardSpecial Hazards of Combustion Products: Highly toxic fumes are imminent.
Flammability and ExplosibilityNotclassified
Agricultural UsesFungicide: 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 nameALGISTAT®; COMPOUND 604®; PHYGON®; PHYGON® PASTE; PHYGON® SEED PROTECTANT; PHYGON® XL; QUINTAR®; QUINTAR® 540F; SANQUINON®; UNIROYAL® 604; USR® 604; U.S. RUBBER® 604
Safety ProfilePoison 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 FatePlant. 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 MethodsCrystallise the quinone from EtOH. [Beilstein 7 IV 2426.]
3,4-DICHLORO-[1,2]NAPHTHOQUINONE 5,6-Dichloro-1,4-naphthoquinone RARECHEM BW GC 0032 Dichloro-1,4-naphthoquinone 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE 1,5-DICHLORO-2,6-NAPHTHOQUINONE RARECHEM BW GA 0111 2,6-Dichloro-1,4-naphthoquinone 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE 2,3-DICHLORO-6-NITRO-1,4-NAPHTHOQUINONE 5,8-Dichloro-1,4-naphthoquinone RARECHEM BW GC 0012 2,5-Dichloro-1,4-naphthoquinone 2,7-Dichloro-1,4-naphthoquinone 6,7-Dichloro-1,4-naphthoquinone 2,8-Dichloro-1,4-naphthoquinone RARECHEM BW GC 0014 RARECHEM BW GC 0036

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