| Identification | More | [Name]
2,3-Dichloro-1,4-naphthoquinone | [CAS]
117-80-6 | [Synonyms]
2，3-Dichloro-1，4-naphthalenedione
2,3-DICHLORO-1,4-NAPHTHAQUINONE
2,3-DICHLORO-1,4-NAPHTHOQUINONE
AURORA KA-5010
DICHLON
DICHLONE
Dichloronaphthoquinone
'LGC' (1114)
PHYGON PASTE(R)
PHYGON(R)
PHYGON XL(R)
UNIROYAL(R)
USR 604(R)
1,4-Naphthalenedione,2,3-dichloro-
1,4-Naphthoquinone, 2,3-dichloro-
2,3-Dichlor-1,4-naftochinon
2,3-Dichlor-1,4-naphthochinon
2,3-Dichloro-1,4-naphthoauinone
2,3-Dichloro-1,4-naphthoquinone (dichlone)
2,3-dichloro-4-naphthalenedione | [EINECS(EC#)]
204-210-5 | [Molecular Formula]
C10H4Cl2O2 | [MDL Number]
MFCD00001677 | [Molecular Weight]
227.04 | [MOL File]
117-80-6.mol |
| Chemical Properties | Back Directory | [Appearance]
YELLOW FINE CRYSTALLINE POWDER | [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 | [Henry's Law Constant]
9.7×103 mol/(m3Pa) at 25℃, HSDB (2015) | [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]
117-80-6(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS06,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H301-H315-H319-H410 | [Precautionary statements ]
P264-P270-P273-P301+P310-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn,N | [Risk Statements ]
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
QL7525000
| [TSCA ]
Yes | [REACH Registrations]
Active | [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 | [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. | [Hazardous Substances Data]
117-80-6(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1300 mg/kg (Bailey, White) |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [General Description]
DICHLONE(117-80-6) 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. | [Reactivity Profile]
DICHLONE 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. | [Air & Water Reactions]
Insoluble in water. | [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. | [Description]
Dichlone is an obsolete foliar fungicide. It has a low aqueous solubility and is not mobile and, based on its chemical properties, it is unlikely to leach to groundwater. It is not persistent in most soil systems. Dichlone has a moderate mammalian toxicity. Little has been reported regarding its toxicity to biodiversity. | [Chemical Properties]
YELLOW FINE CRYSTALLINE POWDER | [Uses]
Fungicide for agriculture and textiles; herbicide. | [Uses]
Fungicide used on fruits, field crops and vegetables | [Production Methods]
The commercial production of diclone follows a concise two-step chlorination-oxidation process. First, 1,4-naphthoquinone is chlorinated with chlorine gas in glacial acetic acid or chlorobenzene using iodine or FeCl₃ as catalyst, adding two chlorine atoms selectively at the 2,3-positions to form crude 2,3-dichloro-1,4-naphthoquinone. The product is isolated by filtration after cooling, washed with water and methanol, and recrystallised from toluene or acetone to technical-grade diclone, | [Flammability and Explosibility]
Notclassified | [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 | [Mechanism of action]
Foliar with protective action by disrupting fungal enzyme activity. It interferes with electron transport in fungal cells, leading to oxidative stress and cell damage, | [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.] | [Pesticide Type]
Fungicide; Algicide |
| Spectrum Detail | Back Directory | [Spectrum Detail]
2,3-Dichloro-1,4-naphthoquinone(117-80-6)MS
2,3-Dichloro-1,4-naphthoquinone(117-80-6)1HNMR
2,3-Dichloro-1,4-naphthoquinone(117-80-6)IR1
2,3-Dichloro-1,4-naphthoquinone(117-80-6)IR2
2,3-Dichloro-1,4-naphthoquinone(117-80-6)Raman
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