Conditions | Yield |
---|---|
With dinitrogen tetraoxide; ferric nitrate In acetone Ambient temperature; | 99% |
With trichloroisocyanuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h; | 99% |
With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
With nitric acid In sulfuric acid at 25℃; | A 98.9% B 0.6% |
4-bromo-1-methoxy-2-nitrobenzene
A
4-bromo-2-nitrophenol
B
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide for 4h; Heating; | A 95% B n/a |
Conditions | Yield |
---|---|
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h; | 85% |
Stage #1: 2-hydroxynitrobenzene In acetonitrile at 80℃; for 0.166667h; Stage #2: With N-chloro-succinimide In acetonitrile at 80℃; for 8h; regioselective reaction; | 80% |
beim Chlorieren; |
4-chloromethoxybenzene
A
4-chloro-2-nitroanisole
B
p-chloro-o-nitrophenol
C
4-chloro-phenol
Conditions | Yield |
---|---|
With nitric acid In sulfuric acid at 25℃; Rate constant; Product distribution; various acid concentrations, molar ratios; | A 83.4% B 17.5% C 5.4% |
With nitric acid In sulfuric acid at 25℃; | A 65.4% B 28% C 9.2% |
4-chloro-phenol
A
p-chloro-o-nitrophenol
B
4-chloro-4-nitrocyclohexa-2,5-dienone
Conditions | Yield |
---|---|
With nitric acid In chloroform at -60℃; for 0.25h; Title compound not separated from byproducts; | A 20% B 80% |
With nitric acid; trifluoroacetic anhydride In diethyl ether at -78℃; for 1.5h; | A 66% B 9% |
3-Chloronitrobenzene
A
2-chloro-4-nitrophenol
B
p-chloro-o-nitrophenol
C
2-chloro-6-nitrophenol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h; | A 79% B 1% C 3% |
With potassium hydroxide; oxygen In ammonia at -35 - -33℃; for 5h; Product distribution; Mechanism; | A .66 g B n/a C n/a |
With Cumene hydroperoxide; potassium tert-butylate In ammonia at -33℃; for 0.25h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With water In tetrahydrofuran at 25℃; for 2.5h; Schlenk technique; | 62% |
1-(benzyloxy)-4-chloro-2-nitrobenzene
A
5-chloro-2-phenyl-1,3-benzoxazole
B
p-chloro-o-nitrophenol
C
4-chloro-2-nitrophenyl benzoate
D
N-(4-chloro-2-hydroxyphenyl)benzamide
Conditions | Yield |
---|---|
In isopropyl alcohol for 10h; Irradiation; | A 3% B 2% C 2% D 50% |
In isopropyl alcohol for 10h; Product distribution; Mechanism; Irradiation; | A 3% B 3% C 2% D 50% |
4-chloro-2-nitrophenyl 4-methylbenzylether
A
p-chloro-o-nitrophenol
C
2-(4-methylphenyl)-5-chlorobenzoxazole
Conditions | Yield |
---|---|
In isopropyl alcohol for 11h; Irradiation; | A 3% B 41% C 4% |
In isopropyl alcohol for 11h; Product distribution; Mechanism; Irradiation; | A 3% B 41% C 4% |
2-hydroxynitrobenzene
A
p-chloro-o-nitrophenol
B
2,4-dichloro-6-nitrophenol
C
2-chloro-6-nitrophenol
Conditions | Yield |
---|---|
With oxone; potassium chloride In acetonitrile at 20℃; for 48h; | A 39% B 18% C 6% |
bis(4-chloro-1,2-benzoquinone 2-oximato)copper(II)
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere; | 5% |
ethanol
A
1-chloro-4-ethoxybenzene
B
p-chloro-o-nitrophenol
C
chlorobenzene
Conditions | Yield |
---|---|
With aluminium trichloride; sulfuryl dichloride |
4-Fluoro-3-nitroaniline
A
p-chloro-o-nitrophenol
B
2-fluoro-5-chloronitrobenzene
Conditions | Yield |
---|---|
und Zersetzen mit Kupfer und wss.HCl.Diazotization; |
Conditions | Yield |
---|---|
With sodium hydroxide |
3-nitro-4-propoxy-aniline
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With hydrogenchloride Diazotization.Behandlung mit CuCl in wss. HCl, zuletzt bei 60grad, und Kochen des Reaktionsprodukts mit AlCl3 in Benzol; |
p-chloro-o-nitrophenol
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With Nitrite; acetic acid Diazotization.man kocht das Produkt mit CuCl; |
Conditions | Yield |
---|---|
With sulfuric acid at 5℃; Diazotization.Erwaermen der Diazoniumsalz-Loesung mit wss. HNO3; |
Conditions | Yield |
---|---|
bei der Zers. der bei Abwesenheit von Mineralsaeure gewonnenen Diazoverbindung mit CuCl; |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; sodium nitrite |
Conditions | Yield |
---|---|
With methanol; chlorine |
Conditions | Yield |
---|---|
With sodium hydroxide | |
With potassium carbonate | |
With sodium hydroxide In water at 120 - 150℃; Autoclave; |
2.6-dimethylphenol
4-chloro-4-nitrocyclohexa-2,5-dienone
A
2,6-dimethyl-4-nitro phenol
B
p-chloro-o-nitrophenol
C
4-chloro-phenol
Conditions | Yield |
---|---|
In chloroform-d1; chloroform -60 deg C to rt; Yield given. Yields of byproduct given; |
tetranitromethane
4-chloromethoxybenzene
A
4-chloro-2-nitroanisole
B
p-chloro-o-nitrophenol
C
4-chloro-2,6-dinitrophenol
D
4-chloro-2-(trinitromethyl)anisole
Conditions | Yield |
---|---|
In dichloromethane Product distribution; Irradiation; var. solvent, var.temperature; |
3-Chloronitrobenzene
A
2-chloro-4-nitrophenol
B
p-chloro-o-nitrophenol
C
2-chloro-6-nitrophenol
D
3,3'-dichloroazoxybenzene
Conditions | Yield |
---|---|
With potassium hydroxide In ammonia at -35 - -33℃; for 5h; Product distribution; Mechanism; | A .34 g B n/a C n/a D .19 g |
Conditions | Yield |
---|---|
With potassium chloride In 1,4-dioxane; water at 50℃; Rate constant; |
1-acetoxy-6-bromohexane
p-chloro-o-nitrophenol
6-(4-chloro-2-nitrophenoxy)-1-hexanol acetate ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 60 - 90℃; | 100% |
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry; | 99% |
With hydrazine hydrate In ethanol at 70℃; for 0.133333h; | 96% |
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.2h; Catalytic behavior; Sealed tube; chemoselective reaction; | 94% |
p-chloro-o-nitrophenol
2-bromobutyric acid ethyl ester
2-(4-chloro-2-nitro-phenoxy)-butyric acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere; | 99% |
With potassium carbonate In acetone for 48h; Heating; |
p-chloro-o-nitrophenol
ethyl bromoacetate
ethyl 4-chloro-2-nitrophenoxyacetate
Conditions | Yield |
---|---|
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Further stages.; | 99% |
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Inert atmosphere; | 99% |
With tetrabutylammomium bromide; potassium carbonate In acetone at 50℃; for 2h; | 91% |
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 2h; |
Conditions | Yield |
---|---|
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromo-pentanoic acid ethyl ester In N,N-dimethyl-formamide for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-chloro-o-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl 2-phenyl-2-bromoacetate In N,N-dimethyl-formamide for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 98% |
With triethylamine In diethyl ether | |
With triethylamine In diethyl ether |
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With potassium hydroxide In dichloromethane; water | 98% |
formaldehyd
p-chloro-o-nitrophenol
3-Methylpiperidine
4-chloro-6-(3'-methylpiperidin-1'-ylmethyl)-2-nitrophenol
Conditions | Yield |
---|---|
In ethanol at 97℃; Heating; | 97% |
p-chloro-o-nitrophenol
allyl bromide
1-(allyloxy)-4-chloro-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 70℃; for 24h; Schlenk technique; | 97% |
With potassium carbonate In acetone for 6h; Heating; |
p-chloro-o-nitrophenol
isopropyl bromide
4-chloro-2-isopropoxynitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 6h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 97% |
With triethylamine In diethyl ether | |
With triethylamine In diethyl ether | |
With triethylamine In diethyl ether |
methyl 2-bromomethylbenzoate
p-chloro-o-nitrophenol
methyl 2-((4-chloro-2-nitrophenoxy)methyl)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 96% |
p-chloro-o-nitrophenol
3-methoxycarbonylbenzyl bromide
methyl 3-((4-chloro-2-nitrophenoxy)methyl)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 96% |
p-chloro-o-nitrophenol
2-bromo-4-chloro-6-nitro-phenol
Conditions | Yield |
---|---|
With bromine In water at 20℃; for 0.166667h; | 95% |
With bromine; acetic acid at 5 - 20℃; | 90.9% |
With bromine; acetic acid at 5 - 20℃; for 3.5h; | 84% |
With bromine; acetic acid at 20℃; for 4h; Cooling with ice; | 76% |
With bromine; acetic acid |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 95% |
Conditions | Yield |
---|---|
With Au NCs/TiO2 In toluene at 130℃; for 24h; Inert atmosphere; | 95% |
With 1,1'-bis-(diphenylphosphino)ferrocene In toluene at 150℃; for 24h; Inert atmosphere; | 80% |
formaldehyd
p-chloro-o-nitrophenol
dimethyl amine
4-chloro-6-(dimethylaminomethyl)-2-nitrophenol
Conditions | Yield |
---|---|
In ethanol at 97℃; Heating; | 94% |
p-chloro-o-nitrophenol
benzyl bromide
1-(benzyloxy)-4-chloro-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 22h; | 94% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
p-chloro-o-nitrophenol
Conditions | Yield |
---|---|
With potassium iodide; potassium carbonate In butanone | 93% |
p-chloro-o-nitrophenol
glycerol
2-hydroxy-5-chloro-aniline
5-chloro-8-hydroxyquinoline hydrochloride
Conditions | Yield |
---|---|
Stage #1: p-chloro-o-nitrophenol; glycerol; 2-hydroxy-5-chloro-aniline With sulfuric acid; boric acid In water at 120℃; for 5h; Large scale; Stage #2: With hydrogenchloride In water Temperature; Large scale; | 92% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur at 130℃; for 2h; | 92% |
N-chloroacetylmorpholine
p-chloro-o-nitrophenol
2-(4-Chloro-2-nitro-phenoxy)-1-morpholin-4-yl-ethanone
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; | 91% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 91% |
tert-butyl 2-(2-(2-hydroxyethoxy)ethoxy)acetate
p-chloro-o-nitrophenol
{2-[2-(4-chloro-2-nitrophenoxy)ethoxy]ethoxy}acetic acid tert-butyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; | 90% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur at 130℃; for 2h; | 90% |
p-chloro-o-nitrophenol
2,2,2-trifluoroethyl trifluoromethanesulphonate
4-chloro-2-nitro-1-(2,2,2-trifluoroethoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 3h; Inert atmosphere; | 90% |
With potassium carbonate In acetone Inert atmosphere; | 90% |
The IUPAC name of Phenol,4-chloro-2-nitro- is 4-chloro-2-nitrophenol. With the CAS registry number 89-64-5, it is also named as 2-Nitro-4-chlorophenol. The product's categories are Intermediates of Dyes and Pigments; Aromatic Phenols; Phenoles and Thiophenoles; Organic Building Blocks; Oxygen Compounds; Phenols. Besides, it is yellow powder, which is insoluble in water. In addition, its molecular formula is C6H4ClNO3 and molecular weight is 173.56.
The other characteristics of this product can be summarized as: (1)EINECS: 201-927-5; (2)ACD/LogP: 2.75; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.69; (5)ACD/LogD (pH 7.4): 1.64; (6)ACD/BCF (pH 5.5): 62.66; (7)ACD/BCF (pH 7.4): 5.62; (8)ACD/KOC (pH 5.5): 646.62; (9)ACD/KOC (pH 7.4): 57.97; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 39.57 cm3; (15)Molar Volume: 111.6 cm3; (16)Surface Tension: 62.2 dyne/cm; (17)Density: 1.554 g/cm3; (18)Flash Point: 100.4 °C; (19)Melting point: 85-87 °C; (20)Enthalpy of Vaporization: 49.89 kJ/mol; (21)Boiling Point: 242.5 °C at 760 mmHg; (22)Vapour Pressure: 0.0218 mmHg at 25 °C.
Preparation of Phenol,4-chloro-2-nitro-: this chemical can be prepared by the hydrolysis and acidification of 2,5-Dichloronitrobenzene. It also can be produced by 4-Chloro-phenol.
This reaction needs Fe(NO3).1.5N2O4 and Acetone at ambient temperature. The yield is 99 %.
Uses of Phenol,4-chloro-2-nitro-: this chemical can be used as intermediate in organic synthesis and intermediate of dye. Furthermore, it can be used to produce 2-Amino-4-chloro-phenol.
This reaction needs Zinc, Ammonium chloride, H2O and Ethanol for 25 min. The yield is 48 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: Clc1cc([N+]([O-])=O)c(O)cc1
(2)InChI: InChI=1/C6H4ClNO3/c7-4-1-2-6(9)5(3-4)8(10)11/h1-3,9H
(3)InChIKey: NWSIFTLPLKCTSX-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C6H4ClNO3/c7-4-1-2-6(9)5(3-4)8(10)11/h1-3,9H
(5)Std. InChIKey: NWSIFTLPLKCTSX-UHFFFAOYSA-N
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