2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With methyltriphenylphosphonium tetrahydroborate In dichloromethane Reduction; Heating; | 100% |
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 1h; Reduction; | 100% |
With butyltriphenylphosphonium tetrahydroborate In dichloromethane at 20℃; for 0.0333333h; | 98% |
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 0.58h; Heating; | 92% |
Stage #1: 2-Chlor-4-nitrophenylazid With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction; | 86% |
Conditions | Yield |
---|---|
With ammonium hydroxide; tetrabutylammomium bromide; copper(l) chloride In water at 140℃; under 24002.4 Torr; Reagent/catalyst; Temperature; Pressure; | 99.45% |
With ethanol; ammonia at 210℃; | |
With ammonium hydroxide at 160℃; |
Conditions | Yield |
---|---|
With sulfuric acid; chlorine at 35℃; under 1500.15 Torr; for 2.5h; Temperature; Flow reactor; | 98.4% |
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 98.5% |
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With 4-amino-1,2,4-triazole; potassium tert-butylate In dimethyl sulfoxide for 4h; Ambient temperature; | 91% |
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; | 86% |
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; | 86% |
Conditions | Yield |
---|---|
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In 1,4-dioxane at 20 - 25℃; Solvent; Green chemistry; | A n/a B 50% |
With hydrogenchloride; sodium chlorate In water; acetic acid at 20℃; for 40h; | A 9% B 32% |
Chlorierung; | |
With methanol; chlorine |
3-Chloronitrobenzene
A
2-chloro-6-nitroaniline
B
4-Chloro-2-nitroaniline
C
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 2,4,6-trichlorosulfenamide; potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.333333h; | A 26% B 7% C 38% |
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given; | |
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide at 20℃; Substitution; Amination; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With benzene |
N-chloroacetanilide
4-nitro-aniline
A
Acetanilid
B
2-Chloro-4-nitroaniline
acetic acid-(2,4,N-trichloro-anilide)
4-nitro-aniline
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With chloroform |
2-amino-5-sulhpoamoylnaphthalene-azo-(2'-chloro-4'-nitrobenzene)
A
5,6-Diamino-naphthalene-1-sulfonic acid amide
B
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
In methanol; water Product distribution; potential -300 mV; constant potential coulometry, acid medium; -750 mV in alkaline medium; |
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With hydrogenchloride; chlorine bei Siedetemperatur; |
hydrogenchloride
4-nitro-aniline
A
4-nitro-2,6-dichloroaniline
B
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
at 210℃; |
N-(2-chlorophenyl)acetamide
nitric acid
acetic anhydride
acetic acid
A
N-(2-chloro-6-nitrophenyl)acetanilide
B
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
at -5℃; und Behandeln des danach isolierten Reaktionsprodukts mit wss.-aethanol. Kalilauge; |
Conditions | Yield |
---|---|
at 25℃; Kinetics; |
1-chloro-2,4-dinitrobenzene
ammonia
A
2,4-diaminonitrobenzene
B
2,5-dinitroaniline
C
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
at 100℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water; acetic acid; nitric acid 2: aqueous sulfuric acid View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; water; nitric acid 2: aqueous sulfuric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous acetic acid 2: acetic acid; acetic acid anhydride; nitric acid / Behandeln des Reaktionsprodukts mit wss.-aethanol.Kalilauge View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 80℃; for 6h; Kinetics; Concentration; Temperature; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; sulfur trioxide; nitric acid / water / 30 - 60 °C 2: tetrabutylammomium bromide; copper(l) chloride; ammonium hydroxide / water / 140 °C / 24002.4 Torr View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 0 - 5 °C / Green chemistry 2: ammonia / water / Autoclave; Heating; Green chemistry View Scheme |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction; | 100% |
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 2.5h; Autoclave; | 99.9% |
With hydrazine hydrate In ethanol at 85℃; for 4h; | 99.2% |
2-Chloro-4-nitroaniline
Acetic formic anhydride
2-chloro-4-nitroformanilide
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 3h; | 100% |
di-tert-butyl dicarbonate
2-Chloro-4-nitroaniline
tert-butyl N-[(tert-butoxy)carbonyl]-N-(2-chloro-4-nitrophenyl)carbamate
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 25℃; for 3h; | 100% |
With dmap In tetrahydrofuran at 20℃; | 100% |
With dmap In tetrahydrofuran at 20℃; for 16h; | |
With dmap In tetrahydrofuran for 1h; Reflux; | |
With dmap In tetrahydrofuran for 1h; Reflux; |
4-methoxy-6-hydroxybenzofuran-5-carboxylic acid
2-Chloro-4-nitroaniline
6-hydroxy-4-methoxy-benzofuran-5-carboxylic acid (2-chloro-4-nitro-phenyl)-amide
Conditions | Yield |
---|---|
With phosphorus trichloride In chlorobenzene for 3h; Heating; | 100% |
Conditions | Yield |
---|---|
With magnesium oxide In acetonitrile for 24h; Heating / reflux; | 100% |
trimethylsilyl ester of hydrocinnamic acid
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 99% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 99% |
2-Chloro-4-nitroaniline
β-naphthol
1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: β-naphthol In water at 20℃; for 0.666667h; | 99% |
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry; Stage #2: β-naphthol In water at 20℃; for 0.166667h; Green chemistry; | 99% |
With hydrogenchloride; sodium nitrite 1.) H2O; Multistep reaction; | |
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 70℃; for 1h; Stage #2: With sodium nitrite In water for 1.5h; Stage #3: β-naphthol Further stages; |
2-Chloro-4-nitroaniline
1,2-dibromo-3-chloro-5-nitro-benzene
Conditions | Yield |
---|---|
With tert.-butylnitrite; bromine; copper(ll) bromide In acetonitrile at 50℃; for 0.5h; | 99% |
Multi-step reaction with 2 steps 1: durch Bromierung View Scheme |
2-Chloro-4-nitroaniline
1,2-bis(2-chloro-4-nitrophenyl)disulfane
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With tetrafluoroboric acid; sodium nitrite In water; acetone at -20 - 0℃; for 0.333333h; Stage #2: With carbon disulfide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In dimethyl sulfoxide at 20℃; for 6h; Concentration; Irradiation; | 99% |
Multi-step reaction with 2 steps 1: (i) (diazotization), (ii) aq. AcOH, SO2, CuCl2, NaNO3 2: aq. HI View Scheme | |
Multi-step reaction with 2 steps 1: aqueous H2SO4 / Diazotization.Behandlung der Diazoniumsalz-Loesung mit Kaliumthiocyanat und FeCl3 2: ethanolic (NH4)2 S View Scheme |
trimethylsilyl isobutyrate
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 98% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 98% |
3-methylbutyric acid trimethylsilyl ester
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 98% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With acetic acid; isopentyl nitrite at 0 - 5℃; | 98% |
N,N-dimethyl-aniline
2-Chloro-4-nitroaniline
N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 5℃; for 0.0833333h; Stage #2: N,N-dimethyl-aniline In water for 0.0833333h; | 98% |
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 20℃; for 0.166667h; Stage #2: N,N-dimethyl-aniline In water at 0 - 5℃; for 0.166667h; | 86% |
Conditions | Yield |
---|---|
With sodium chlorate; sulfuric acid; hydrogen bromide In water at 35 - 65℃; | 97.62% |
With acetic acid; potassium bromide In water at 30℃; for 1h; | 95% |
durch Bromierung; |
trimethylsilyl 2,2-dimethylpropionate
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 97% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2.75h; Stage #2: aniline With sodium hydroxide In water at 0 - 5℃; for 3h; pH=6; Concentration; Solvent; | 95.7% |
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2.5h; Stage #2: aniline With sodium hydroxide In water at 0 - 5℃; for 3h; pH=6; | 94.2% |
trimethylsilyl acetate
2-Chloro-4-nitroaniline
N-(2-chloro-4-nitrophenyl)acetamide
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 95% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 95% |
trimethylsilyl 2-methylbenzoate
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 95% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; ytterbium(III) triflate In dichloromethane; water for 6h; Heating; | 95% |
N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; urea; sodium nitrite In 1,4-dioxane; water at 0 - 5℃; for 2h; Stage #2: N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine In 1,4-dioxane at 0 - 5℃; for 3h; pH=6; Solvent; | 94.19% |
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 5℃; for 2.5h; Sonication; Stage #2: urea In water for 0.25h; Stage #3: 1-amino-3-methylbenzene With sodium hydroxide In water at 0 - 5℃; for 4h; pH=6; | 92.25% |
diethyl 2-ethoxymethylenemalonate
2-Chloro-4-nitroaniline
2-[(2-Chloro-4-nitro-phenylamino)-methylene]-malonic acid diethyl ester
Conditions | Yield |
---|---|
for 1h; Heating; | 92% |
Conditions | Yield |
---|---|
With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide at 30℃; for 1h; Green chemistry; | 92% |
Stage #1: 2-Chloro-4-nitroaniline With Nitrogen dioxide In acetonitrile at -20℃; Diazotization; Stage #2: With calcium bis(hypophosphite); Fe2SO4*7H2O In methanol; acetonitrile at 20℃; Dediazonation; | 87% |
With sulfuric acid; ethyl acetate; sodium nitrite In water at 50 - 55℃; for 0.5h; | 50% |
Multi-step reaction with 3 steps 1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 91 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 9 percent / aq. HBr / acetonitrile / 0.5 h / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 91 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 2 percent / aq. HI; HBF4 / acetonitrile / 0.5 h / 60 °C View Scheme |
2-Chloro-4-nitroaniline
cyclohexanecarbaldehyde
N-(2-chloro-4-nitrophenyl)cyclohexanecarboxamide
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-4-nitroaniline With tert.-butylnitrite; trimethylsilylazide In tetrahydrofuran at 0℃; Stage #2: cyclohexanecarbaldehyde With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; sodium t-butanolate In tetrahydrofuran at -25℃; | 92% |
4,6-dihydroxy-2-mercaptopyrimidine
orthoformic acid triethyl ester
2-Chloro-4-nitroaniline
Conditions | Yield |
---|---|
In butan-1-ol for 4h; Reflux; | 91% |
4-nitro-benzoyl chloride
2-Chloro-4-nitroaniline
N-(2-chloro-4-nitrophenyl)-4-nitrobenzamide
Conditions | Yield |
---|---|
In chlorobenzene at 130 - 132℃; for 2.5h; | 90% |
With N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 0.5h; Microwave irradiation; | 71% |
The IUPAC name of this product is 2-chloro-4-nitroaniline. With the CAS registry number 121-87-9, it is also named as 1-Amino-2-chloro-4-nitrobenzene; 4-12-00-01675 (Beilstein Handbook Reference); Aniline, 2-chloro-4-nitro-; BRN 0638657; Benzenamine, 2-chloro-4-nitro-; CCRIS 2648; ortho-Chloro-para-nitroaniline. The product's categories are intermediates of dyes and pigments, pharmacetical, functional materials and organic nonlinear optical materials.
The 2-Chloro-4-nitroaniline is yellow crystalline powder which is soluble in ethanol, ether and benzene, slightly soluble in water and acid, insoluble in crude petrol. It is stable and incompatible with strong oxidizing agents, strong bases, strong acids. This chemical is used in organic synthesis, also used as dye intermediates.
The 2-Chloro-4-nitroaniline is harmful if swallowed. Inhalation, ingestion or skin contact with material may cause severe injury or death. So people must avoid any skin contact and not breathe dust. Fire may produce irritating, corrosive and/or toxic gases. This product may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.46; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.46; (4)ACD/LogD (pH 7.4): 2.46; (5)ACD/BCF (pH 5.5): 43.43; (6)ACD/BCF (pH 7.4): 43.43; (7)ACD/KOC (pH 5.5): 517.54; (8)ACD/KOC (pH 7.4): 517.54; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.646; (13)Molar Refractivity: 41.92 cm3; (14)Molar Volume: 115.5 cm3; (15)Polarizability: 16.62×10-24 cm3; (16)Surface Tension: 62.2 dyne/cm; (17)Enthalpy of Vaporization: 56.84 kJ/mol; (18)Vapour Pressure: 0.000219 mmHg at 25°C; (19)Exact Mass: 172.003955; (20)MonoIsotopic Mass: 172.003955; (21)Topological Polar Surface Area: 71.8; (22)Heavy Atom Count: 11.
People can use the following data to convert to the molecule structure. SMILES: Clc1cc([N+]([O-])=O)ccc1N; InChI: InChI=1/C6H5ClN2O2/c7-5-3-4(9(10)11)1-2-6(5)8/h1-3H,8H2; InChIKey: LOCWBQIWHWIRGN-UHFFFAOYAC. 2-Chloro-4-nitroaniline has many suppliers, such as Hanghzou Fayer Chemicals Co., Ltd., Hebei Yongtai-Create Chemicals Co., Ltd. and Jiangsu International Economic-Technical Cooperation Corp..
The following is the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 1800mg/kg (1800mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC | National Technical Information Service. Vol. OTS0536149, |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 138, 1954. | |
mouse | LD50 | oral | 1250mg/kg (1250mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981. | |
mouse | LDLo | intraperitoneal | 500mg/kg (500mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 5, Pg. 337, 1953. |
rat | LD50 | oral | 6430mg/kg (6430mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981. |
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