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2,3-Dichloro-1,4-naphthoquinone

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2,3-Dichloro-1,4-naphthoquinone Basic information

Product Name:
2,3-Dichloro-1,4-naphthoquinone
Synonyms:
  • quintar540f
  • Sanquinon
  • U.s. rubber 604
  • u.s.rubber604
  • Uniroyal
  • USR 604
  • usr604
  • usrubber604
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
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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)
refractive index 
1.5410 (estimate)
Flash point:
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
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)
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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 Data
117-80-6(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 1300 mg/kg (Bailey, White)

MSDS

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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

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.

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

2,3-Dichloro-1,4-naphthoquinoneSupplier

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