117-80-6 Usage
Chemical Properties
YELLOW FINE CRYSTALLINE POWDER
Uses
Different sources of media describe the Uses of 117-80-6 differently. You can refer to the following data:
1. Fungicide for agriculture and textiles; herbicide.
2. Fungicide used on fruits, field crops and vegetables
3. 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
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
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 117-80-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117-80:
(5*1)+(4*1)+(3*7)+(2*8)+(1*0)=46
46 % 10 = 6
So 117-80-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H
117-80-6Relevant articles and documents
White et al.
, p. 585,586-588 (1969)
FRIES REACTION AND DAKIN REARRANGEMENT IN BENZO-2,1,3-THIADIAZOLES
Belen'kaya, I. A.,Krokhina, G. P.,Sirik, S. A.,Andronati, S. A.
, p. 1356 - 1359 (1987)
The Fries rearrangement of 4- and 5-acetoxybenzo-2,1,3-thiadiazoles has given 4-hydroxy-7-acetyl- and 5-hydroxy-4-acetylbenzo-2,1,3-thiadiazoles, which on oxidation afford mixtures of 5-chloro-4,7-dioxo- and 5,6-dichloro-4,7-dioxobenzo-2,1,3-thiadiazole and of 6-chloro-4,5-dioxo- and 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadiazole.Reaction of 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadiazole with ortho-phenylenediamine gives 4,5-dichloro-2,1,3-thiadiazolophenazine.
Method for preparing 2,3-dichloro-1,4-naphthoquinone from wastes in production process of 2-chloro-1,4-naphthoquinone
-
Paragraph 0024; 0025, (2017/07/19)
The invention discloses a method for preparing 2,3-dichloro-1,4-naphthoquinone from wastes in the production process of a 2-chloro-1,4-naphthoquinone in the technical field of chemical industry. The method for preparing the 2,3-dichloro-1,4-naphthoquinone from the wastes in the production process of 2-chloro-1,4-naphthoquinone comprises the following specific steps: (S1) metering the wastes accumulated in production and feeding the wastes into a reaction kettle; (S2) feeding washed, centrifuged and dried materials into the reaction kettle again for discoloring treatment; (S3) carrying out detection through a GS gas chromatography analysis method; (S4) feeding pretreated tailings to the reaction bottle; (S5) adding industrial sodium acetate; and (S6) naturally cooling and stirring for about 30 minutes and then removing excessive chlorine. The 2,3-dichloro-1,4-naphthoquinone is prepared from waste residues generated in the production process of 2-chloro-1,4-naphthoquinone as a starting material through pretreatment and deep chlorination, so that the problem of waste residue emission is solved, the environment pressure is relieved, the environmental pollution is avoided and the production cost is reduced.
Reaction of semiquinoid compounds derived from N-arylsulfonyl-p-quinonemono- and diimines with tosylhydrazine
Avdeenko,Zhukova
, p. 816 - 819 (2007/10/03)
Reaction of 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-1-ones with tosylhydrazine gives rise to N-arylsulfonyl-N-p-tolylsulfonyl-2,3,5,6-tetrachloroaminophenols. With 4-arylsulfonylimino-2,2,3-trichloro-1,2,3,4-tetrahydronaphthalen-1-ones and 4-arylsulfonylimino-2-dihalo-1,2,3,4-tetrahydronaphthalen-1-ones reaction products are 4-arylsulfonylamido-2,3-dichloro-4-p-tolylsulfonylhydrazido-1,4-dihydronaphthalen-1-ones and 2-p-tolylsulfonyl-1,4-naphthoquinone-4-diazide respectively. First stage of the processes consists in dehydrohalogenation yielding the corresponding N-arylsulfonyl-p-quinonimines.
The treatment of pests using substituted naphthoquinones
-
, (2008/06/13)
Naphthoquinone compounds of the formula I wherein R1 and R2 are each, independently, selected from H and OH and R3 and R4 are each, independently, selected from H, halo and 1-4C alkyl groups, provided that when R1 and R2 are each H, R3 and R4 cannot both be H, have use as pesticides particularly in the treatment of acarids and insects. A pesticidal composition comprises at least one compound of the formula I together with an inert carrier.
