Product Name

  • Name

    2,6-Dichloro-4-nitroaniline

  • EINECS 202-746-4
  • CAS No. 99-30-9
  • Article Data53
  • CAS DataBase
  • Density 1.624 g/cm3
  • Solubility 1 g/L in water at 60 °C
  • Melting Point 190-192 °C(lit.)
  • Formula C6H4Cl2N2O2
  • Boiling Point 323 °C at 760 mmHg
  • Molecular Weight 207.016
  • Flash Point 149.1 °C
  • Transport Information UN 2811
  • Appearance yellow granular powder and chunks
  • Safety 22-26-36-37/39
  • Risk Codes 33-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 99-30-9 (2,6-Dichloro-4-nitroaniline)
  • Hazard Symbols IrritantXi,HarmfulXn
  • Synonyms Aniline,2,6-dichloro-4-nitro- (6CI,8CI);1-Amino-2,6-dichloro-4-nitrobenzene;2,6-Dichloro-4-nitrobenzenamine;2,6-Dichloro-p-nitroaniline;4-Nitro-2,6-dichloroaniline;AL 50;Allisan;Batran;Bortran;Botran;Botran 75B;Botran 75W;CNA;DCNA;Ditranil;NSC 218;U-2069;
  • PSA 71.84000
  • LogP 3.58820

Synthetic route

4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
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%
2,6-dichloro-p-phenylenediamine
609-20-1

2,6-dichloro-p-phenylenediamine

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;92%
2,6-dichloro-4-aminonitrobenzene
59992-52-8

2,6-dichloro-4-aminonitrobenzene

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
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%
4-nitro-aniline
100-01-6

4-nitro-aniline

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

Conditions
ConditionsYield
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
22134-75-4

4-amino-3,5-dichloro-benzenesulfonamide

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With ammonium nitrate; sulfuric acid at 0 - 5℃; for 0.25h;21%
4-nitro-aniline
100-01-6

4-nitro-aniline

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

C

bis(4-nitrophenyl)diazene
3646-57-9, 89103-79-7

bis(4-nitrophenyl)diazene

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In ethanol at 25℃; for 0.0833333h;A n/a
B 15%
C 9%
diethyl ether
60-29-7

diethyl ether

N,N-dichloro-4-nitro-aniline
408326-80-7

N,N-dichloro-4-nitro-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

4-bromo-2,6-dichloroaniline
697-88-1

4-bromo-2,6-dichloroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With nitric acid; acetic acid
1,3-dichloro-2,5-dinitro-benzene
13633-34-6

1,3-dichloro-2,5-dinitro-benzene

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With ethanol; ammonia in der Kaelte;
N,N-dichloro-4-nitro-aniline
408326-80-7

N,N-dichloro-4-nitro-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether
With diethyl ether
With acetic anhydride
N,N-dichloro-4-nitro-aniline
408326-80-7

N,N-dichloro-4-nitro-aniline

acetic anhydride
108-24-7

acetic anhydride

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With benzene
With acetic acid
With tert-butyl alcohol
acetic acid-(2,4,N-trichloro-anilide)
112160-74-4

acetic acid-(2,4,N-trichloro-anilide)

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With chloroform
2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With hydrogenchloride; chlorine
With hydrogenchloride; dihydrogen peroxide In water at 30 - 40℃; Green chemistry;
2,6-dichloro-N-nitroaniline
54381-76-9

2,6-dichloro-N-nitroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With trifluoroacetic acid-d1 In chloroform-d1 at 30℃; Rate constant; Mechanism; kinetic isotope effect;
hydrogenchloride
7647-01-0

hydrogenchloride

chlorine
7782-50-5

chlorine

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

4-nitro-aniline
100-01-6

4-nitro-aniline

benzene
71-43-2

benzene

aqueous sodium hypochlorite

aqueous sodium hypochlorite

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

bis-(2,6-dichloro-4-nitro-phenyl)-diazene-N-oxide

bis-(2,6-dichloro-4-nitro-phenyl)-diazene-N-oxide

Conditions
ConditionsYield
bei 2.5-stdg. Behandeln;
hydrogenchloride
7647-01-0

hydrogenchloride

4-nitro-aniline
100-01-6

4-nitro-aniline

potassium chlorate

potassium chlorate

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

4-nitro-aniline
100-01-6

4-nitro-aniline

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

bis(4-nitrophenyl)diazene
3646-57-9, 89103-79-7

bis(4-nitrophenyl)diazene

4-bromo-2,6-dichloro-N-nitro-aniline
71756-91-7

4-bromo-2,6-dichloro-N-nitro-aniline

sulfuric acid
7664-93-9

sulfuric acid

acetic acid
64-19-7

acetic acid

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

1,3-dichloro-2,5-dinitro-benzene
13633-34-6

1,3-dichloro-2,5-dinitro-benzene

ammonia
7664-41-7

ammonia

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

hydrogenchloride
7647-01-0

hydrogenchloride

diethyl ether
60-29-7

diethyl ether

N,N-dichloro-4-nitro-aniline
408326-80-7

N,N-dichloro-4-nitro-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
at -20℃;
N,N-dichloro-4-nitro-aniline
408326-80-7

N,N-dichloro-4-nitro-aniline

petroleum ether

petroleum ether

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

bis(4-nitrophenyl)diazene
3646-57-9, 89103-79-7

bis(4-nitrophenyl)diazene

2,4,6-trichloro-N-nitroaniline
71756-89-3

2,4,6-trichloro-N-nitroaniline

A

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

B

2,4,6-trichloroaniline
634-93-5

2,4,6-trichloroaniline

Conditions
ConditionsYield
With silica gel at 140℃; for 2h; Product distribution; Further Variations:; Reagents;A n/a
B 20 % Chromat.
4-bromo-aniline
106-40-1

4-bromo-aniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform
2: glacial acetic acid; nitric acid
View Scheme
2-bromo-4,6-dinitroaniline
1817-73-8

2-bromo-4,6-dinitroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

2,6-Dichloroaniline
608-31-1

2,6-Dichloroaniline

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With sulfuric acid; nitric acid Heating;
1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

3,4,5-trichloronitrobenzen
20098-48-0

3,4,5-trichloronitrobenzen

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

1-bromo-2,6-dichloro-4-nitrobenzene
98137-94-1

1-bromo-2,6-dichloro-4-nitrobenzene

Conditions
ConditionsYield
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
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromo-N-(2,6-dichloro-4-nitrophenyl)acetamide

2-bromo-N-(2,6-dichloro-4-nitrophenyl)acetamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 60℃;94%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

nitratocarbonylbis(triphenylphosphine)rhodium
22654-78-0, 99664-53-6

nitratocarbonylbis(triphenylphosphine)rhodium

RhCO(P(C6H5)3)2HNC6H2Cl2NO2

RhCO(P(C6H5)3)2HNC6H2Cl2NO2

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

4-azido-5-fluoro-pyridine-3-carbaldehyde
1378039-78-1

4-azido-5-fluoro-pyridine-3-carbaldehyde

[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichloro-4-nitrophenyl)-amine
1378040-29-9

[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichloro-4-nitrophenyl)-amine

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;92%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

phenol
108-95-2

phenol

C12H7Cl2N3O3

C12H7Cl2N3O3

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

Benzophenone-3
131-57-7

Benzophenone-3

1-[2-hydroxy-4-methoxy-5-(2,6-dichloro-4-nitrophenylazo)phenyl]-1-phenylmethanone
1243203-32-8

1-[2-hydroxy-4-methoxy-5-(2,6-dichloro-4-nitrophenylazo)phenyl]-1-phenylmethanone

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

N-cyclohexyl-2-(phenylamino)-2-(p-tolyl)acetamide

N-cyclohexyl-2-(phenylamino)-2-(p-tolyl)acetamide

(E)-N-cyclohexyl-2-((4-((2,6-dichloro-4-nitrophenyl)diazenyl)phenyl)amino)-2-(p-tolyl)acetamide

(E)-N-cyclohexyl-2-((4-((2,6-dichloro-4-nitrophenyl)diazenyl)phenyl)amino)-2-(p-tolyl)acetamide

Conditions
ConditionsYield
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
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

N-(2,6-dichloro-4-nitrophenyl)pyrrole
93516-62-2

N-(2,6-dichloro-4-nitrophenyl)pyrrole

Conditions
ConditionsYield
With acetic acid Heating;82%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

2-(2-bromophenyl)-N-cyclohexyl-2-(phenylamino)acetamide
1383479-59-1

2-(2-bromophenyl)-N-cyclohexyl-2-(phenylamino)acetamide

(E)-2-(2-bromophenyl)-N-cyclohexyl-2-((4-((2,6-dichloro-4-nitrophenyl)diazenyl)phenyl)amino)acetamide

(E)-2-(2-bromophenyl)-N-cyclohexyl-2-((4-((2,6-dichloro-4-nitrophenyl)diazenyl)phenyl)amino)acetamide

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

m-acetylamino-N,N-diethylanilne
6375-46-8

m-acetylamino-N,N-diethylanilne

N,N-diethyl-4-(2,6-dichloro-4-nitrophenylazo)-3-acetylaminoaniline
88458-16-6

N,N-diethyl-4-(2,6-dichloro-4-nitrophenylazo)-3-acetylaminoaniline

Conditions
ConditionsYield
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
64-18-6

formic acid

4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

N-(2,6-dichloro-4-nitrophenyl)formamide
70106-94-4

N-(2,6-dichloro-4-nitrophenyl)formamide

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

2-(2'-anthraquinonylamino-3'-hydroxy)-4-anilino-6-chloro-s-triazine
1395499-28-1

2-(2'-anthraquinonylamino-3'-hydroxy)-4-anilino-6-chloro-s-triazine

C29H17Cl2N7O5
1395499-25-8

C29H17Cl2N7O5

Conditions
ConditionsYield
In nitrobenzene at 60 - 65℃; for 5h;76%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

α-naphthol
90-15-3

α-naphthol

C16H9Cl2N3O3

C16H9Cl2N3O3

Conditions
ConditionsYield
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%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

2,6-dichloro-p-phenylenediamine
609-20-1

2,6-dichloro-p-phenylenediamine

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride75%
With ethanol; ammonium chloride; zinc
With ethanol; nickel Hydrogenation;
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

10-undecenoic acid
112-38-9

10-undecenoic acid

Undec-10-enoic acid (2,6-dichloro-4-nitro-phenyl)-amide
76691-53-7

Undec-10-enoic acid (2,6-dichloro-4-nitro-phenyl)-amide

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In dichloromethane75%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

β-naphthol
135-19-3

β-naphthol

1-(2,6-dichloro-4-nitro-phenylazo)-[2]naphthol
23648-85-3

1-(2,6-dichloro-4-nitro-phenylazo)-[2]naphthol

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

(1R,2R)-N,N-dimethylcyclohexane-1,2-diamine
320778-92-5

(1R,2R)-N,N-dimethylcyclohexane-1,2-diamine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

C15H20Cl2N4O3
1365611-35-3

C15H20Cl2N4O3

Conditions
ConditionsYield
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
99-30-9

4-nitro-2,6-dichloroaniline

ethyl 2-phenyldiazoacetate
22065-57-2

ethyl 2-phenyldiazoacetate

ethyl 2-((2,6-dichloro-4-nitrophenyl)amino)-2-phenylacetate

ethyl 2-((2,6-dichloro-4-nitrophenyl)amino)-2-phenylacetate

Conditions
ConditionsYield
With C43H37Br2CuN3P2(1+)*ClO4(1-) In dichloromethane at 0 - 20℃; for 5h; Schlenk technique; Inert atmosphere; chemoselective reaction;71%
4-nitro-2,6-dichloroaniline
99-30-9

4-nitro-2,6-dichloroaniline

1-phenylpentane-1,4-dione
583-05-1

1-phenylpentane-1,4-dione

2,6-dichloro-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)aniline

2,6-dichloro-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)aniline

Conditions
ConditionsYield
With indium; acetic acid In toluene for 12h; Inert atmosphere; Reflux;67%

2,6-Dichloro-4-nitroaniline Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

2,6-Dichloro-4-nitroaniline Specification

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%.

Benzenamine,2,6-dichloro-4-nitro- can be used to produce 1,2,3-trichloro-5-nitro-benzene

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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