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117-80-6

Basic Information
CAS No.: 117-80-6
Name: 2,3-Dichloro-1,4-naphthoquinone
Article Data: 70
Molecular Structure:
Molecular Structure of 117-80-6 (2,3-Dichloro-1,4-naphthoquinone)
Formula: C10H4Cl2O2
Molecular Weight: 227.047
Synonyms: 2,3-Dichloronaphthoquinone-1,4;2,3-Dichloronaphthoquinone;Sanquinon;1,4-Naphthalenedione, 2,3-dichloro-;1,4-Naphthalenedione,2,3-dichloro-;Algistat;1,4-Naphthoquinone, 2,3-dichloro-;EPA Pesticide Chemical Code 029601;USR 604;2,3-dichloronaphthalene-1,4-dione;US Rubber 604;CNQ;Phygon;2,3-Dichloro-1,4-naphthalenedione;Uniroyal;Dichlone;Phygon Seed Protectant;Dichloronaphthoquinone;2, 3-Dichloro-.alpha.-naphthoquinone;Quintar 540F;2,3-Dichloro-1, 4-naphthalenedione;Dichlone [BSI:ISO];2,3-Dichloro-1,4-naphthaquinone;Quintar;2, 3-Dichloronaphthoquinone;U.S. Rubber 604;
EINECS: 204-210-5
Density: 1.54 g/cm3
Melting Point: 194-197 °C(lit.)
Boiling Point: 304 °C at 760 mmHg
Flash Point: 127.5 °C
Solubility: 0.008 g/L in water
Appearance: yellow crystalline powder
Hazard Symbols: HarmfulXn; DangerousN
Risk Codes: 22-36/38-50/53
Safety: 26-60-61
Transport Information: UN 2811 6.1/PG 3
PSA: 34.14000
LogP: 2.75480
Synthetic route
1010-60-2

2-chloro-1,4-naphthoquinone

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With pyridine; thionyl chloride In benzene for 3.5h; Heating;88%
With chlorine; acetic acid
With chlorine; acetic acid at 95 - 100℃;265 g
130-15-4

[1,4]naphthoquinone

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With pyridine; thionyl chloride In benzene for 3.5h; Heating;87%
With hydrogenchloride; sodium chlorate; tetrabutylammomium bromide In ethyl acetate at 50℃; for 20h;73%
With iodine; acetic acid durch Chlorierung;
571-60-8

1,4-Dihydroxynaphthalene

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With pyridine; thionyl chloride In benzene for 3h; Heating;74%
Multi-step reaction with 3 steps
1: 92 percent / SOCl2 / benzene / 2 h / Heating
2: 71 percent / SCl2, S2Cl2, pyridine / benzene / 1.5 h / Heating
3: 88 percent / SOCl2, pyridine / benzene / 3.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 92 percent / SOCl2 / benzene / 2 h / Heating
2: 87 percent / SOCl2, pyridine / benzene / 3.5 h / Heating
View Scheme
2395-97-3

9,10-dimethoxyanthracene

A

117-80-6

2,3-Dichloro-1,4-naphthoquinone

B

1010-60-2

2-chloro-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride; iodosylbenzene; sodium hydrogencarbonate In diethyl ether for 0.5h; Chlorination; oxidation;A 21%
B 67%
With hydrogenchloride; sulfuric acid for 0.5h; Chlorination; oxidation;A 31%
B 36%
139719-08-7

2,3-Dichloro-N-p-tolylsulfonyl-1,4-naphthoquinonemonoimine

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With water22%
3669-52-1

4-acetyl-1-naphthol

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide In acetonitrile for 1h; Heating;21%
91-20-3

naphthalene

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With chromyl chloride; acetic acid
64-17-5

ethanol

2243-28-9

2,2,3,4,4-pentachloro-1-oxo-1,2,3,4-tetrahydronaphthaline

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
at 120 - 130℃;
90-15-3

α-naphthol

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride; potassium chlorate
With sulfuric acid Verduennen mit Wasser, Zusatz von Salzsaeure und Eintragen von KClO3;
With sulfuric acid; chlorine; iron(II) sulfate; acetic acid at 10 - 20℃; zuletzt bei 100-120grad;
durch Sulfurierung und nachf. Behandlung mit Kaliumchlorat und Salzsaeure;
Multi-step reaction with 2 steps
1: glacial acetic acid; chlorine
2: diluted acetic acid / 120 - 130 °C / im Druckrohr
View Scheme
84-86-6

4-amino-1-naphthalenesufonic acid

117-80-6

2,3-Dichloro-1,4-naphthoquinone

Conditions
ConditionsYield
With sulfuric acid; chlorine; iron at 10 - 20℃; zuletzt bei 90grad;
With sulfuric acid; chlorine; iron(II) sulfate at 10 - 20℃; zuletzt bei 90grad;
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  • 2,3-Dichloro-1,4-naphthoquinoneCAS NO.: 117-80-6

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2,3-Dichloro-1,4-naphthoquinone, with the CAS registry number 117-80-6 and EINECS registry number 204-210-5, has the systematic of 2,3-dichloronaphthalene-1,4-dione. And the molecular formula of this chemical is C10H4Cl2O2. It is a kind of yellow fine crystalline powder, and belongs to the product category of Intermediates of Dyes and Pigments. What's more, it is used as agricultural fungicide.

The physical properties of 2,3-Dichloro-1,4-naphthoquinone are as following: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.35; (4)ACD/LogD (pH 7.4): 2.35; (5)ACD/BCF (pH 5.5): 36.07; (6)ACD/BCF (pH 7.4): 36.07; (7)ACD/KOC (pH 5.5): 453.11; (8)ACD/KOC (pH 7.4): 453.11; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.634; (14)Molar Refractivity: 52.57 cm3; (15)Molar Volume: 146.9 cm3; (16)Polarizability: 20.84×10-24cm3; (17)Surface Tension: 55.3 dyne/cm; (18)Density: 1.54 g/cm3; (19)Flash Point: 127.5 °C; (20)Enthalpy of Vaporization: 54.44 kJ/mol; (21)Boiling Point: 304 °C at 760 mmHg; (22)Vapour Pressure: 0.000897 mmHg at 25°C.

Preparation of 2,3-Dichloro-1,4-naphthoquinone: It can be prepared by the chlorination of 1,4 - naphthoquinone. The reaction will need will occur in the alcohols, phenols and hydrocarbons solvent. And the catalyst ferrous powder or iron chloride.

Uses of 2,3-Dichloro-1,4-naphthoquinone: It can react with 5-methyl-benzene-1,3-diol to produce 3-hydroxy-1-methyl-benzo[b]naphtho[2,3-d]furan-6,11-quinone. This reaction will need reagent NaOEt, and the solvent ethanol. And the yield is about 60%.

2,3-Dichloro-1,4-naphthoquinone can react with 5-methyl-benzene-1,3-diol to produce 3-hydroxy-1-methyl-benzo[b]naphtho[2,3-d]furan-6,11-quinone

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful if swallowed. What's more, it is very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: This material and/or its container must be disposed of as hazardous waste; Avoid release to the environment. Refer to special instructions safety data sheet; In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c1c(cccc1)C(=O)C(/Cl)=C2/Cl
(2)InChI: InChI=1/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H
(3)InChIKey: SVPKNMBRVBMTLB-UHFFFAOYAD

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 570, 1983.
mouse LD50 oral 440mg/kg (440mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 47, 1982.
rabbit LD50 skin 500mg/kg (500mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A137, Pg. 1983,
rat LD50 oral 160mg/kg (160mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 16(5), Pg. 52, 1972.