Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide In water at -8 - 20℃; for 2h; Temperature; Reagent/catalyst; | 99.5% |
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.133333h; Green chemistry; | 99% |
Stage #1: 4-nitro-aniline With hydrogenchloride In water at 63℃; for 0.5h; Stage #2: With chlorine In water for 0.166667h; Temperature; Time; | 98.65% |
Conditions | Yield |
---|---|
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; | 92% |
2,6-dichloro-4-aminonitrobenzene
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; under 37503.8 Torr; for 24h; chemoselective reaction; | 90% |
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 |
4-amino-3,5-dichloro-benzenesulfonamide
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With ammonium nitrate; sulfuric acid at 0 - 5℃; for 0.25h; | 21% |
4-nitro-aniline
A
4-nitro-2,6-dichloroaniline
B
2-Chloro-4-nitroaniline
C
bis(4-nitrophenyl)diazene
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hypochlorite In ethanol at 25℃; for 0.0833333h; | A n/a B 15% C 9% |
Conditions | Yield |
---|---|
With nitric acid; acetic acid |
1,3-dichloro-2,5-dinitro-benzene
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With ethanol; ammonia in der Kaelte; |
N,N-dichloro-4-nitro-aniline
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With hydrogenchloride; diethyl ether | |
With diethyl ether | |
With acetic anhydride |
N,N-dichloro-4-nitro-aniline
acetic anhydride
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With benzene | |
With acetic acid | |
With tert-butyl alcohol |
acetic acid-(2,4,N-trichloro-anilide)
2-Chloro-4-nitroaniline
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With chloroform |
Conditions | Yield |
---|---|
With hydrogenchloride; chlorine | |
With hydrogenchloride; dihydrogen peroxide In water at 30 - 40℃; Green chemistry; |
2,6-dichloro-N-nitroaniline
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
With trifluoroacetic acid-d1 In chloroform-d1 at 30℃; Rate constant; Mechanism; kinetic isotope effect; |
hydrogenchloride
chlorine
2-Chloro-4-nitroaniline
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
bei 2.5-stdg. Behandeln; |
hydrogenchloride
4-nitro-aniline
A
4-nitro-2,6-dichloroaniline
B
2-Chloro-4-nitroaniline
hydrogenchloride
ethanol
dihydrogen peroxide
4-nitro-aniline
A
4-nitro-2,6-dichloroaniline
B
bis(4-nitrophenyl)diazene
4-bromo-2,6-dichloro-N-nitro-aniline
sulfuric acid
acetic acid
4-nitro-2,6-dichloroaniline
hydrogenchloride
diethyl ether
N,N-dichloro-4-nitro-aniline
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
at -20℃; |
N,N-dichloro-4-nitro-aniline
A
4-nitro-2,6-dichloroaniline
B
bis(4-nitrophenyl)diazene
2,4,6-trichloro-N-nitroaniline
A
4-nitro-2,6-dichloroaniline
B
2,4,6-trichloroaniline
Conditions | Yield |
---|---|
With silica gel at 140℃; for 2h; Product distribution; Further Variations:; Reagents; | A n/a B 20 % Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chloroform 2: glacial acetic acid; nitric acid View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 0 - 5 °C / Green chemistry 2: ammonia / water / Autoclave; Heating; Green chemistry 3: hydrogenchloride; dihydrogen peroxide / water / 30 - 40 °C / Green chemistry View Scheme |
4-nitro-2,6-dichloroaniline
3,4,5-trichloronitrobenzen
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite at 50 - 70℃; for 1h; Stage #2: With acetic acid at 5℃; for 1h; Stage #3: With hydrogenchloride; copper(l) chloride In water at 15 - 70℃; for 2h; | 98.5% |
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite at 5 - 70℃; for 0.333333h; Stage #2: With acetic acid for 0.5h; Stage #3: With hydrogenchloride; copper(l) chloride In water at 25 - 70℃; for 1h; | 75% |
With copper(I) chloride; hydrogenchloride; sulfuric acid In acetic acid for 1h; | 47% |
With methyl nitrite; sulfuric acid; acetic acid Diazotization.Behandeln mit Kupfer(I)-chlorid in konz. Salzsaeure; | |
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite at 50℃; for 0.666667h; Sandmeyer Reaction; Stage #2: With acetic acid at 5℃; for 1h; Sandmeyer Reaction; Stage #3: With hydrogenchloride; copper(l) chloride at 15 - 70℃; for 1.83333h; Sandmeyer Reaction; |
4-nitro-2,6-dichloroaniline
1-bromo-2,6-dichloro-4-nitrobenzene
Conditions | Yield |
---|---|
With tert.-butylnitrite; copper(I) bromide In acetonitrile at 20℃; for 6h; Cooling with ice; | 97% |
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃; for 10h; Cooling with ice; | 92% |
With hydrogen bromide; acetic acid; sodium nitrite |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20 - 60℃; | 94% |
4-nitro-2,6-dichloroaniline
nitratocarbonylbis(triphenylphosphine)rhodium
Conditions | Yield |
---|---|
With KOH In methanol; acetone to an acetone soln. of Rh complex were added equimolar quantity of nitroaniline (in acetone) and KOH in MeOH; solvents were evpd. in vac., red residue extd. with benzene and filtered from KNO3; solvent removed in vac., crystals pptd. with hexane, filtered, washed with hexane and dried in air; elem. anal.; | 92% |
4-nitro-2,6-dichloroaniline
4-azido-5-fluoro-pyridine-3-carbaldehyde
[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichloro-4-nitrophenyl)-amine
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite In 1,2-dimethoxyethane; water at 0 - 5℃; for 1.25h; Stage #2: phenol With sodium carbonate In water at 0 - 70℃; for 7h; pH=9 - 10; | 84.5% |
4-nitro-2,6-dichloroaniline
Benzophenone-3
1-[2-hydroxy-4-methoxy-5-(2,6-dichloro-4-nitrophenylazo)phenyl]-1-phenylmethanone
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: Benzophenone-3 In water at 0 - 20℃; Alkaline conditions; | 84% |
4-nitro-2,6-dichloroaniline
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With hydrogenchloride In water at 40 - 60℃; for 2h; Stage #2: With sodium nitrite In water at 0℃; for 2h; Stage #3: N-cyclohexyl-2-(phenylamino)-2-(p-tolyl)acetamide With acetic acid In methanol; water at 0 - 20℃; for 24h; | 84% |
cis,trans-2,5-dimethoxytetrahydrofuran
4-nitro-2,6-dichloroaniline
N-(2,6-dichloro-4-nitrophenyl)pyrrole
Conditions | Yield |
---|---|
With acetic acid Heating; | 82% |
4-nitro-2,6-dichloroaniline
2-(2-bromophenyl)-N-cyclohexyl-2-(phenylamino)acetamide
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With hydrogenchloride In water at 40 - 60℃; for 2h; Stage #2: With sodium nitrite In water at 0℃; for 2h; Stage #3: 2-(2-bromophenyl)-N-cyclohexyl-2-(phenylamino)acetamide With acetic acid In methanol; water at 0 - 20℃; for 24h; | 81% |
4-nitro-2,6-dichloroaniline
m-acetylamino-N,N-diethylanilne
N,N-diethyl-4-(2,6-dichloro-4-nitrophenylazo)-3-acetylaminoaniline
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With tert.-butylnitrite; naphthalene-1,5-disulfonate In 1,2-dimethoxyethane at 25℃; for 0.5h; Stage #2: m-acetylamino-N,N-diethylanilne With sodium carbonate; naphthalene-1,5-disulfonate In water at 0℃; for 0.166667h; pH=4 - 6; | 78.77% |
Stage #1: 4-nitro-2,6-dichloroaniline With naphthalene-1,5-disulfonate In ethyl acetate at 50℃; for 0.166667h; Stage #2: With tert.-butylnitrite In ethyl acetate at 25℃; for 0.333333h; Stage #3: m-acetylamino-N,N-diethylanilne With hydrogenchloride In water at 0 - 5℃; for 0.316667h; |
formic acid
4-nitro-2,6-dichloroaniline
N-(2,6-dichloro-4-nitrophenyl)formamide
Conditions | Yield |
---|---|
Stage #1: formic acid With acetic anhydride at 70 - 80℃; for 1h; Stage #2: 4-nitro-2,6-dichloroaniline for 3h; Heating; | 78% |
Stage #1: formic acid With acetic anhydride at 55 - 60℃; for 0.333333h; Stage #2: 4-nitro-2,6-dichloroaniline at 55℃; for 6.33333h; | 65% |
4-nitro-2,6-dichloroaniline
2-(2'-anthraquinonylamino-3'-hydroxy)-4-anilino-6-chloro-s-triazine
C29H17Cl2N7O5
Conditions | Yield |
---|---|
In nitrobenzene at 60 - 65℃; for 5h; | 76% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite In 1,2-dimethoxyethane; water at 0 - 5℃; for 1.25h; Stage #2: α-naphthol With sodium carbonate In water at 0 - 70℃; for 7h; pH=9 - 10; | 75.61% |
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride | 75% |
With ethanol; ammonium chloride; zinc | |
With ethanol; nickel Hydrogenation; |
4-nitro-2,6-dichloroaniline
10-undecenoic acid
Undec-10-enoic acid (2,6-dichloro-4-nitro-phenyl)-amide
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate In dichloromethane | 75% |
4-nitro-2,6-dichloroaniline
β-naphthol
1-(2,6-dichloro-4-nitro-phenylazo)-[2]naphthol
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With sulfuric acid; sodium nitrite In 1,2-dimethoxyethane; water at 0 - 5℃; for 1.25h; Stage #2: β-naphthol With sodium carbonate In water at 0 - 70℃; for 7h; pH=9 - 10; | 73.28% |
4-nitro-2,6-dichloroaniline
(1R,2R)-N,N-dimethylcyclohexane-1,2-diamine
1,1'-carbonyldiimidazole
C15H20Cl2N4O3
Conditions | Yield |
---|---|
Stage #1: 4-nitro-2,6-dichloroaniline With potassium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1,1'-carbonyldiimidazole In tetrahydrofuran; 1,4-dioxane at 0 - 20℃; Inert atmosphere; Stage #3: (1R,2R)-N,N-dimethylcyclohexane-1,2-diamine In tetrahydrofuran; 1,4-dioxane at 20℃; for 20h; Inert atmosphere; | 73% |
4-nitro-2,6-dichloroaniline
ethyl 2-phenyldiazoacetate
Conditions | Yield |
---|---|
With C43H37Br2CuN3P2(1+)*ClO4(1-) In dichloromethane at 0 - 20℃; for 5h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 71% |
Conditions | Yield |
---|---|
With indium; acetic acid In toluene for 12h; Inert atmosphere; Reflux; | 67% |
The Benzenamine,2,6-dichloro-4-nitro-, with the CAS registry number 99-30-9, is also known as 2,6-Dichloro-4-nitrobenzenamine. It belongs to the product categories of Intermediates of Dyes and Pigments; Pharmaceutical intermediate. Its EINECS number is 202-746-4. This chemical's molecular formula is C6H4Cl2N2O2 and molecular weight is 207.01. What's more, its systematic name is 2,6-dichloro-4-nitroaniline. Its classification codes are: (1)Agricultural Chemical; (2)Fungicide, bactericide, wood preservative; (3)Mutation data; (4)Tumor data. It should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides, strong acids, heat and fire. It should also be prevented from direct sunlight. It is used as dye intermediates.
Physical properties of Benzenamine,2,6-dichloro-4-nitro- are: (1)ACD/LogP: 3.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.54; (4)ACD/LogD (pH 7.4): 3.54; (5)ACD/BCF (pH 5.5): 287.48; (6)ACD/BCF (pH 7.4): 287.48; (7)ACD/KOC (pH 5.5): 2002.05; (8)ACD/KOC (pH 7.4): 2002.05; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49.06 Å2; (13)Index of Refraction: 1.655; (14)Molar Refractivity: 46.82 cm3; (15)Molar Volume: 127.4 cm3; (16)Polarizability: 18.56×10-24cm3; (17)Surface Tension: 63.8 dyne/cm; (18)Density: 1.624 g/cm3; (19)Flash Point: 149.1 °C; (20)Enthalpy of Vaporization: 56.49 kJ/mol; (21)Boiling Point: 323 °C at 760 mmHg; (22)Vapour Pressure: 0.000269 mmHg at 25°C.
Preparation: this chemical can be prepared by paranitroaniline chloridizing in the mixture of hydrochloric acid and glacial acetic acid.
Uses of Benzenamine,2,6-dichloro-4-nitro-: it can be used to produce 1,2,3-trichloro-5-nitro-benzene. It will need reagents conc. aq. HCl, conc. aq. H2SO4, Cu2Cl2 and solvent acetic acid with the reaction time of 1 hour. The yield is about 47%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. It has a danger of cumulative effects. You should not breathe dust. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(cc(Cl)c1N)[N+]([O-])=O
(2)Std. InChI: InChI=1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2
(3)Std. InChIKey: BIXZHMJUSMUDOQ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
duck | LD50 | oral | > 2gm/kg (2000mg/kg) | Pesticide Manual. Vol. 9, Pg. 265, 1991. | |
guinea pig | LD50 | oral | 1450mg/kg (1450mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 343, 1966. | |
mammal (species unspecified) | LD50 | unreported | 1500mg/kg (1500mg/kg) | "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 87, 1971. | |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03022. | |
mouse | LD50 | oral | 1500mg/kg (1500mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 343, 1966. | |
mouse | LD50 | skin | > 5gm/kg (5000mg/kg) | Pesticide Manual. Vol. 9, Pg. 265, 1991. | |
mouse | LD50 | unreported | 4490mg/kg (4490mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(11), Pg. 4, 1989. |
rabbit | LD50 | skin | > 2gm/kg (2000mg/kg) | Pesticide Manual. Vol. 9, Pg. 265, 1991. | |
rat | LC50 | inhalation | > 21600mg/m3/1 (21600mg/m3) | Pesticide Manual. Vol. 9, Pg. 265, 1991. | |
rat | LD50 | oral | 2400mg/kg (2400mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Office of Toxic Substances Report. Vol. OTS. |
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