Conditions | Yield |
---|---|
With pyridine; thionyl chloride In benzene for 3.5h; Heating; | 88% |
With chlorine; acetic acid | |
With chlorine; acetic acid at 95 - 100℃; | 265 g |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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 |
9,10-dimethoxyanthracene
A
2,3-Dichloro-1,4-naphthoquinone
B
2-chloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
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% |
2,3-Dichloro-N-p-tolylsulfonyl-1,4-naphthoquinonemonoimine
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With water | 22% |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide In acetonitrile for 1h; Heating; | 21% |
Conditions | Yield |
---|---|
With chromyl chloride; acetic acid |
ethanol
2,2,3,4,4-pentachloro-1-oxo-1,2,3,4-tetrahydronaphthaline
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
at 120 - 130℃; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With sulfuric acid; chlorine; iron at 10 - 20℃; zuletzt bei 90grad; | |
With sulfuric acid; chlorine; iron(II) sulfate at 10 - 20℃; zuletzt bei 90grad; |
2,2,3,4,4-pentachloro-1-oxo-1,2,3,4-tetrahydronaphthaline
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With ethanol at 120 - 130℃; im Druckrohr; | |
With acetic acid at 120 - 130℃; im Druckrohr; |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium chlorate |
1-hydroxy-2,4-dinitronaphthalene
A
2,3-Dichloro-1,4-naphthoquinone
B
2-chloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With hydrogenchloride; potassium chlorate |
2,3-dichloro-[1]naphthol
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid |
2,3-dichloro-1,2,3,4-tetrahydronaphthalene-1,4-dione
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With sodium acetate; chlorine; acetic acid at 10 - 20℃; zuletzt bei Siedetemperatur; |
[1,4]naphthoquinone-mono-chlorimin
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid at 25 - 30℃; |
2,3-dichloro-5,8-dihydro-naphthalene-1,4-diol
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With chromium(VI) oxide |
2,2,3,4,4-pentachloro-1-oxo-1,2,3,4-tetrahydronaphthaline
acetic acid
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
at 120 - 130℃; |
Conditions | Yield |
---|---|
With sodium hydroxide; D-glucose |
2,6-dichloro-1,4-benzoquinone
2,3-Dichlor-1,4-naphthosemichinon
A
2,3-Dichloro-1,4-naphthoquinone
B
2,6-dichloro-p-benzoquinone anion radical
Conditions | Yield |
---|---|
In gas at 150℃; Rate constant; |
4-chloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)benzenesulfonamide
A
2,3-Dichloro-1,4-naphthoquinone
B
2,2,3,3-Tetrachloro-1,2,3,4-tetrahydronaphthalene-1,4-dione
Conditions | Yield |
---|---|
With water Yield given. Yields of byproduct given; |
2,3-Dichloro-1,4-naphthoquinone
Conditions | Yield |
---|---|
With Tris-HCl buffer; dodecyl-N,N-dimethylamine N-oxide |
Conditions | Yield |
---|---|
In dichloromethane at 21.4℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 21.4℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 23.4℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 21.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 23.4℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 21.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 22.1℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane at 22.1℃; Equilibrium constant; |
morpholine
2,3-Dichloro-1,4-naphthoquinone
2-chloro-3-morpholin-4-yl-[1,4]naphthoquinone
Conditions | Yield |
---|---|
In water at 50℃; for 0.333333h; | 100% |
With water at 50℃; for 0.5h; | 98% |
With triethylamine In diethyl ether at 20℃; for 24h; | 64% |
2,3-Dichloro-1,4-naphthoquinone
aniline
2-chloro-3-(phenylamino)naphthalene-1,4-dione
Conditions | Yield |
---|---|
With water at 50℃; for 0.25h; | 100% |
Stage #1: aniline With triethylamine In water for 0.0833333h; Green chemistry; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In water at 50 - 60℃; Green chemistry; regioselective reaction; | 99% |
In methanol Heating; | 98% |
2,3-Dichloro-1,4-naphthoquinone
1,1-bis-(4-methoxyphenyl)ethylene
2-chloro-3-<2,2-bis(p-methoxyphenyl)ethenyl>-1,4-naphthoquinone
Conditions | Yield |
---|---|
With pyridine In tetrachloromethane for 1h; Quantum yield; Ambient temperature; Irradiation; | 100% |
With pyridine In tetrachloromethane for 0.0166667h; Ambient temperature; Irradiation; | 100% |
2,3-Dichloro-1,4-naphthoquinone
potassium phtalimide
2,2'-(1,4-dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(isoindoline-1,3-dione)
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 3h; Inert atmosphere; Reflux; | 100% |
In acetonitrile at 85℃; for 3h; | 97% |
In acetonitrile at 85℃; for 3h; | 97% |
Conditions | Yield |
---|---|
With potassium hydroxide In pyridine at 90℃; | 100% |
Conditions | Yield |
---|---|
In ethanol for 5h; Heating; | 100% |
In ethanol Reflux; | 60% |
With N,N-diethylaniline Reflux; |
2,3-Dichloro-1,4-naphthoquinone
1-amino-2-propene
2-(2-propenylamino)-3-chloronaphthalene-1,4-dione
Conditions | Yield |
---|---|
In water at 20℃; for 0.5h; | 100% |
In ethanol for 6h; | 95% |
In ethanol at 20℃; for 60h; | 80% |
2,3-Dichloro-1,4-naphthoquinone
2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at -23℃; for 3h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2,3-Dichloro-1,4-naphthoquinone With sodium azide In ethanol at 20℃; for 1h; Substitution; Stage #2: tri(4-chlorophenyl)phosphine Cyclization; | 100% |
2,3-Dichloro-1,4-naphthoquinone
4-methoxyphenylboronic acid
2,3-bis(4-methoxyphenyl)naphthalene-1,4-dione
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; benzene for 4h; Suzuki coupling; Heating; | 100% |
2,3-Dichloro-1,4-naphthoquinone
ethyl 2-sulfanylacetate
ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetate
Conditions | Yield |
---|---|
With water at 50℃; for 2h; | 100% |
In water at 50℃; for 2h; | 100% |
In ethanol at 80 - 90℃; | 97% |
2,3-Dichloro-1,4-naphthoquinone
3-nitrophenylsulfonamide
N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-3-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Sealed tube; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate In ethanol at 20℃; | 99% |
In water Reflux; Green chemistry; | 98% |
In water Reflux; | 98% |
Conditions | Yield |
---|---|
In ethanol at 20 - 60℃; for 16h; | 99% |
In methanol at 20℃; for 10h; | 97% |
Stage #1: 4-amino-phenol With triethylamine In water for 0.0833333h; Green chemistry; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In water at 50 - 60℃; Green chemistry; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; benzene for 6h; Suzuki coupling; Heating; | 99% |
2,3-Dichloro-1,4-naphthoquinone
2-Thioxo-1,3,4,11-tetrathia-cyclopenta[b]anthracene-5,10-dione
Conditions | Yield |
---|---|
In acetone at 20℃; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-cresol With laundry detergent (Ariel) In water for 0.0833333h; Micellar solution; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In water at 60℃; for 0.5h; Micellar solution; chemoselective reaction; | 99% |
Stage #1: p-cresol With Ariel laundry detergent In water for 0.0833333h; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In water at 60℃; for 0.5h; chemoselective reaction; | 99% |
With caesium carbonate In tetrahydrofuran at 20℃; for 76h; | 95% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; | 99% |
In water at 20℃; for 0.166667h; | 99% |
2,3-Dichloro-1,4-naphthoquinone
3-amino-N-ethylbenzenesulfonamide
C18H15ClN2O4S
Conditions | Yield |
---|---|
In ethanol; water at 120℃; for 72h; | 99% |
2,3-Dichloro-1,4-naphthoquinone
N,N'-dimesitylformamidine
Conditions | Yield |
---|---|
Stage #1: 2,3-Dichloro-1,4-naphthoquinone; N,N'-dimesitylformamidine In acetonitrile at 110℃; for 48h; Sealed; Stage #2: With sodium hydrogencarbonate at 20 - 60℃; for 16h; | 99% |
2,3-Dichloro-1,4-naphthoquinone
phenethylamine
2-chloro-3-(phenethylamino)naphthalene-1,4-dione
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 1.5h; | 99% |
In ethanol at 20℃; | 76% |
In ethanol Reflux; | 62% |
In ethanol at 20℃; for 3h; | 48.4% |
2,3-Dichloro-1,4-naphthoquinone
cyclohexylamine
2-chloro-3-(cyclohexylamino)naphthalene-1,4-dione
Conditions | Yield |
---|---|
In ethanol at 20℃; for 6h; chemoselective reaction; | 99% |
In acetonitrile at 20℃; for 1.5h; | 98% |
With triethylamine In diethyl ether at 20℃; for 24h; | 75% |
piperidine
2,3-Dichloro-1,4-naphthoquinone
2-chloro-3-piperidyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; | 98% |
In water at 20℃; for 0.166667h; | 98% |
With triethylamine In diethyl ether at 20℃; for 24h; | 75% |
With ethanol |
2,3-Dichloro-1,4-naphthoquinone
sulfanilamide
4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
Conditions | Yield |
---|---|
In water for 3h; Reflux; | 98% |
In ethanol at 115℃; for 72h; | 38.9% |
With acetic acid; N,N-diethylaniline | |
In ethanol Reflux; |
2,3-Dichloro-1,4-naphthoquinone
1,4-phenylenediamine
2-(4-amino-anilino)-3-chloro-[1,4]naphthoquinone
Conditions | Yield |
---|---|
In DMF (N,N-dimethyl-formamide) at 20℃; for 2h; | 98% |
With ethanol | |
In water; N,N-dimethyl-formamide | |
In ethanol Reflux; |
2,3-Dichloro-1,4-naphthoquinone
4,5-diaminopyridine-6<1H>-thione
11-amino-6-chlorobenzo-8,10-diazaphenothiazin-5-one
Conditions | Yield |
---|---|
With sodium carbonate In chloroform for 3.5h; Heating; | 98% |
2,3-Dichloro-1,4-naphthoquinone
4-amino-N,N-dimethylaniline
2-chloro-3-(4-N,N-dimethylaminoanilino)-1,4-naphthoquinone
Conditions | Yield |
---|---|
In ethanol at 20℃; for 5h; | 98% |
Conditions | Yield |
---|---|
In methanol Reflux; | 98% |
With cerium(III) chloride In ethanol at 65 - 70℃; | 95% |
With sodium carbonate In ethanol at 20℃; for 6h; | 88.7% |
Conditions | Yield |
---|---|
In water at 20℃; for 1h; | 98% |
In ethanol at 80 - 90℃; |
Conditions | Yield |
---|---|
With caesium carbonate In tetrahydrofuran at 20℃; for 20h; | 98% |
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%.
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. |
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