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4-Chloro-3-nitroaniline is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

635-22-3

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635-22-3 Usage

Uses

Intermediate in the manufacture of azo dyes, pharmaceuticals, and other organic compounds.

Hazard

Toxic by ingestion and inhalation.

Safety Profile

Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx and Cl-.

Check Digit Verification of cas no

The CAS Registry Mumber 635-22-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 5 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 635-22:
(5*6)+(4*3)+(3*5)+(2*2)+(1*2)=63
63 % 10 = 3
So 635-22-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClN2O2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H,8H2

635-22-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chloro-3-nitroaniline

1.2 Other means of identification

Product number -
Other names 4-Chloro-3-nitrobenzenamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:635-22-3 SDS

635-22-3Synthetic route

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Conditions
ConditionsYield
With isopropyl alcohol; potassium hydroxide for 0.166667h; Microwave irradiation; regioselective reaction;98%
With isopropyl alcohol; potassium hydroxide for 0.366667h; Microwave irradiation; chemoselective reaction;95%
With potassium hydroxide; nickel-incorporated hexagonal mesoporous aluminophosphate In isopropyl alcohol at 82.84℃; for 3h;88%
4-chloro-aniline
106-47-8

4-chloro-aniline

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Conditions
ConditionsYield
With sodium nitrate; sulfuric acid at 0 - 5℃; for 3h;94%
With sulfuric acid; guanidine nitrate at 0 - 5℃; for 1h;75%
With sulfuric acid; nitric acid
durch Nitrierung;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-azido-3-nitro-4-chlorobenzene
13243-32-8

1-azido-3-nitro-4-chlorobenzene

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

1,1-dimethylethyl 4-chloro-3-nitrophenylcarbamate

1,1-dimethylethyl 4-chloro-3-nitrophenylcarbamate

Conditions
ConditionsYield
With Decaborane; palladium on activated charcoal In methanol at 20℃; for 3h;A 68%
B 30%
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

H2NC6H3(Cl)NO2
6283-25-6

H2NC6H3(Cl)NO2

Conditions
ConditionsYield
With hydrogen; iron; acetic acid; palladium dichloride In ethanol at 20 - 25℃; under 258.6 - 2327.2 Torr;A n/a
B 61%
With benzophenone; triethylamine In isopropyl alcohol for 2h; Product distribution; Irradiation;A 18%
B n/a
With hydrogenchloride; ethanol; tin(ll) chloride
4-chloro-aniline
106-47-8

4-chloro-aniline

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -20℃;
chloroform
67-66-3

chloroform

acetic acid-(2,4,N-trichloro-anilide)
112160-74-4

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

3-nitro-aniline
99-09-2

3-nitro-aniline

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

acetic acid-(2,4,N-trichloro-anilide)
112160-74-4

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

3-nitro-aniline
99-09-2

3-nitro-aniline

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Conditions
ConditionsYield
With chloroform
sulfuric acid
7664-93-9

sulfuric acid

nitric acid
7697-37-2

nitric acid

4-chloro-aniline
106-47-8

4-chloro-aniline

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

acid

acid

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

H2NC6H3(Cl)NO2
6283-25-6

H2NC6H3(Cl)NO2

Conditions
ConditionsYield
Electrolysis;
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

alkali

alkali

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

H2NC6H3(Cl)NO2
6283-25-6

H2NC6H3(Cl)NO2

Conditions
ConditionsYield
Electrolysis;
hydrogenchloride
7647-01-0

hydrogenchloride

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

tin dichloride

tin dichloride

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

2-chloro-6-nitroaniline
769-11-9

2-chloro-6-nitroaniline

methanol
67-56-1

methanol

chlorine
7782-50-5

chlorine

3-nitro-aniline
99-09-2

3-nitro-aniline

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

2,4,6-trichloro-3-nitro-aniline
62406-71-7

2,4,6-trichloro-3-nitro-aniline

C

2-nitro-4-amino-1,5-dichlorobenzene
34033-44-8

2-nitro-4-amino-1,5-dichlorobenzene

acetic acid
64-19-7

acetic acid

3-nitro-aniline
99-09-2

3-nitro-aniline

calcium hypochlorite

calcium hypochlorite

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

2,4,6-trichloro-3-nitro-aniline
62406-71-7

2,4,6-trichloro-3-nitro-aniline

C

2,6-dichloro-3-nitroaniline
13785-48-3

2,6-dichloro-3-nitroaniline

D

2,4-dichloro-3-nitroaniline
129825-24-7

2,4-dichloro-3-nitroaniline

sulfuric acid
7664-93-9

sulfuric acid

nitric acid
7697-37-2

nitric acid

4-chloro-aniline
106-47-8

4-chloro-aniline

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
at -20℃;
3-nitro-aniline
99-09-2

3-nitro-aniline

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

2.4-dichloro-3-nitro-aniline, 2.6-dichloro-3-nitro-aniline and 2.4.6-trichloro-3-nitro-aniline

2.4-dichloro-3-nitro-aniline, 2.6-dichloro-3-nitro-aniline and 2.4.6-trichloro-3-nitro-aniline

Conditions
ConditionsYield
With calcium hypochlorite; acetic acid at 40 - 60℃;
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

4-chloro-1,3-phenylenediamine
5131-60-2

4-chloro-1,3-phenylenediamine

C

H2NC6H3(Cl)NO2
6283-25-6

H2NC6H3(Cl)NO2

D

m-phenylenediamine
108-45-2

m-phenylenediamine

Conditions
ConditionsYield
With hydrogen; Pt/γ-Fe2O3 nanocomposite In methanol at 29.84℃; under 75.0075 Torr; Product distribution;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

N-(4-chloro-3-nitrophenyl)acetamide
5540-60-3

N-(4-chloro-3-nitrophenyl)acetamide

Conditions
ConditionsYield
With acetic anhydride In diethyl ether; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran100%
With acetic anhydride In diethyl ether; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran96%
Acetylieren;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

3-chloro-3-oxopropanoic acid methyl ester
37517-81-0

3-chloro-3-oxopropanoic acid methyl ester

N-(4-chloro-3-nitro-phenyl)-malonamic acid methyl ester
852312-59-5

N-(4-chloro-3-nitro-phenyl)-malonamic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

3-(Trifluoromethyl)benzoyl chloride
2251-65-2

3-(Trifluoromethyl)benzoyl chloride

N-(4-chloro-3-nitrophenyl)-3-(trifluoromethyl)benzamide
1001341-80-5

N-(4-chloro-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 6h;100%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

N-(4-chloro-3-nitrophenyl)cyclohexanecarboxamide
458554-50-2

N-(4-chloro-3-nitrophenyl)cyclohexanecarboxamide

Conditions
ConditionsYield
Stage #1: 4-Chloro-3-nitroaniline; cyclohexanylcarbonyl chloride With pyridine In dichloromethane at 20℃; for 18h;
Stage #2: With hydrogenchloride In dichloromethane; water
100%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

N-(3-amino-4-chlorophenyl)cyclobutanecarboxamide

N-(3-amino-4-chlorophenyl)cyclobutanecarboxamide

Conditions
ConditionsYield
Stage #1: 4-Chloro-3-nitroaniline; Cyclobutanecarbonyl chloride With pyridine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: With potassium carbonate In methanol; water
Stage #3: With hydrogen; Raney nickel In methanol under 760.051 Torr; for 18h;
100%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

C11H11ClN2O3
1286584-86-8

C11H11ClN2O3

Conditions
ConditionsYield
Stage #1: 4-Chloro-3-nitroaniline; Cyclobutanecarbonyl chloride With pyridine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: With potassium carbonate In methanol; water for 0.5h;
100%
With pyridine In dichloromethane at 0 - 20℃; for 1h;
formaldehyd
50-00-0

formaldehyd

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

sodium methylate
124-41-4

sodium methylate

(4-Chloro-3-nitro-phenyl)-methoxymethyl-amine
129367-46-0

(4-Chloro-3-nitro-phenyl)-methoxymethyl-amine

Conditions
ConditionsYield
97%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1,1-dimethylethyl 4-chloro-3-nitrophenylcarbamate

1,1-dimethylethyl 4-chloro-3-nitrophenylcarbamate

Conditions
ConditionsYield
In ethanol at 50℃; for 72h;96%
In tetrahydrofuran for 12h; Reflux;78%
In tetrahydrofuran for 20h; Reflux;78%
NH-pyrazole
288-13-1

NH-pyrazole

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

3-nitro-4-(1H-pyrazol-1-yl)aniline

3-nitro-4-(1H-pyrazol-1-yl)aniline

Conditions
ConditionsYield
With D-galacturonic acid; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 80 - 100℃; Inert atmosphere; Green chemistry;96%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

acetic anhydride
108-24-7

acetic anhydride

N-(4-chloro-3-nitrophenyl)acetamide
5540-60-3

N-(4-chloro-3-nitrophenyl)acetamide

Conditions
ConditionsYield
With nickel dichloride at 20℃; for 0.166667h; Neat (no solvent);95%
With sulfuric acid for 2h; Heating;81%
In dichloromethane at 20℃; for 2h;80%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

N-(4-chloro-3-nitro-phenyl)-oxalamic acid ethyl ester

N-(4-chloro-3-nitro-phenyl)-oxalamic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane95%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

4-chloro-1,3-phenylenediamine
5131-60-2

4-chloro-1,3-phenylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 20℃; for 0.0333333h; Catalytic behavior;95%
With sodium tetrahydroborate In water at 20℃; for 0.5h; chemoselective reaction;91%
With sodium tetrahydroborate; water; nickel at 20℃; for 2.5h;90%
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 7h; Catalytic behavior; chemoselective reaction;
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

2-acetyl-5-chlorothiophene
6310-09-4

2-acetyl-5-chlorothiophene

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

C17H12Cl2N2O3S2
1037752-15-0

C17H12Cl2N2O3S2

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;94.2%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

para-chloroacetophenone
99-91-2

para-chloroacetophenone

benzaldehyde
100-52-7

benzaldehyde

MWW6021

MWW6021

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;94.1%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

sodium methansulfinate
20277-69-4

sodium methansulfinate

1-(4-chloro-3-nitrophenyl)-2-(methylsulfonyl)diazene

1-(4-chloro-3-nitrophenyl)-2-(methylsulfonyl)diazene

Conditions
ConditionsYield
Stage #1: 4-Chloro-3-nitroaniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1.08333h;
Stage #2: sodium methansulfinate In dichloromethane at 0 - 20℃;
94%
Stage #1: 4-Chloro-3-nitroaniline With tetrafluoroboric acid In water for 0.25h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5h;
Stage #3: sodium methansulfinate In dichloromethane at 0 - 20℃;
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

2-Acetyl-5-bromothiophene
5370-25-2

2-Acetyl-5-bromothiophene

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

C17H12BrClN2O3S2
1037752-13-8

C17H12BrClN2O3S2

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;92.6%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(4-chloro-3-nitrophenyl)methanesulfonamide
135937-15-4

N-(4-chloro-3-nitrophenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 24h;92%
With pyridine In tetrahydrofuran for 24h;92%
With pyridine for 4h; Ambient temperature;
With pyridine In tetrahydrofuran at 20℃; for 12h;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

chloroacetyl chloride
79-04-9

chloroacetyl chloride

α-chloro-N-(m-nitro-p-chlorophenyl)acetamide

α-chloro-N-(m-nitro-p-chlorophenyl)acetamide

Conditions
ConditionsYield
In toluene for 3h; Heating;92%
With triethylamine In dichloromethane at 0 - 20℃;80%
With triethylamine In dichloromethane at 0 - 20℃;80%
With triethylamine In dichloromethane at 0 - 20℃; for 20h;
With triethylamine In ethanol at 0 - 90℃; for 3h;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

4-sulfanylphenol
637-89-8

4-sulfanylphenol

4-(4-amino-2-nitro-phenylsulfanyl)-phenol
530135-26-3

4-(4-amino-2-nitro-phenylsulfanyl)-phenol

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 16h;92%
With potassium carbonate In ethanol for 6h; Heating;5%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

benzaldehyde
100-52-7

benzaldehyde

C21H16ClFN2O3
1037752-06-9

C21H16ClFN2O3

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;91.5%
2-Acetyl-5-bromothiophene
5370-25-2

2-Acetyl-5-bromothiophene

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

benzaldehyde
100-52-7

benzaldehyde

C19H14BrClN2O3S
1037751-94-2

C19H14BrClN2O3S

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;91%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

4-(pyridin-4-yl)benzaldehyde
99163-12-9

4-(pyridin-4-yl)benzaldehyde

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (4-chloro-3-nitrophenylamino)(4-(pyridine-4-yl)phenyl)methylphosphonate
1356925-26-2

diethyl (4-chloro-3-nitrophenylamino)(4-(pyridine-4-yl)phenyl)methylphosphonate

Conditions
ConditionsYield
With poly(ethylene glycol)sulfonic acid In toluene at 40 - 50℃; for 2.5h; Kabachnik-Fields reaction;91%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

4-chloro-6-(pentylthio)-1H-pyrazolo[3,4-d]pyrimidine

4-chloro-6-(pentylthio)-1H-pyrazolo[3,4-d]pyrimidine

N-(4-chloro-3-nitrophenyl)-6-(pentylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

N-(4-chloro-3-nitrophenyl)-6-(pentylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
In ethanol at 80℃; for 2h;91%
In ethanol at 80℃; for 2h;
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

thiophene-2-carbonyl isothiocyanate
68967-37-3

thiophene-2-carbonyl isothiocyanate

N-(4-chloro-3-nitrophenyl)-N'-(thiophene-2-carbonyl)thiocarbamide

N-(4-chloro-3-nitrophenyl)-N'-(thiophene-2-carbonyl)thiocarbamide

Conditions
ConditionsYield
at 27℃; for 2h;91%
furfural
98-01-1

furfural

2-Acetyl-5-bromothiophene
5370-25-2

2-Acetyl-5-bromothiophene

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

C17H12BrClN2O4S
1037752-22-9

C17H12BrClN2O4S

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;90%
furfural
98-01-1

furfural

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

C19H14ClFN2O4
1037752-07-0

C19H14ClFN2O4

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 50℃; Mannich reaction;90%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

2,3-dihydro-1,4-benzodioxin-6-carboxylic acid
4442-54-0

2,3-dihydro-1,4-benzodioxin-6-carboxylic acid

N-(4-chloro-3-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

N-(4-chloro-3-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: 4-Chloro-3-nitroaniline With pyridine In dichloromethane at 20℃; for 3h;
90%
4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

potassium thioacyanate
333-20-0

potassium thioacyanate

acetyl chloride
75-36-5

acetyl chloride

1-acetyl-3-(4-chloro-3-nitrophenyl)thiourea

1-acetyl-3-(4-chloro-3-nitrophenyl)thiourea

Conditions
ConditionsYield
Stage #1: potassium thioacyanate; acetyl chloride In water; acetone for 3h;
Stage #2: 4-Chloro-3-nitroaniline In water; acetone for 5h; Reflux;
90%

635-22-3Relevant academic research and scientific papers

Biomass Sucrose-Derived Cobalt@Nitrogen-Doped Carbon for Catalytic Transfer Hydrogenation of Nitroarenes with Formic Acid

Yuan, Man,Long, Yu,Yang, Jin,Hu, Xiwei,Xu, Dan,Zhu, Yangyang,Dong, Zhengping

, p. 4156 - 4165 (2018/11/01)

Fabrication of non-noble metal-based heterogeneous catalysts by a facile and cost-effective strategy for ecofriendly catalytic transfer hydrogenation (CTH) is of great significance for organic transformations. A cobalt@nitrogen-doped carbon (Co@NC) catalyst was prepared from renewable biomass-derived sucrose, harmless melamine, and earth-abundant Co(AcO)2 as the precursor materials by hydrothermal treatment and carbonization. Co nanoparticles (NPs) were coated with NC shells and uniformly embedded in the NC framework. The as-obtained Co@NC-600 (carbonized at 600 °C) catalyst exhibited excellent catalytic efficiency for CTH of various functionalized nitroarenes with formic acid (FA) as hydrogen donor in aqueous solution. The uniformly incorporated N atoms in the C matrix and the encapsulated Co NPs showed synergistic effects in the CTH reactions. A mechanistic analysis indicated that the protons from FA were activated by Co sites after being captured by N atoms, and then reacted with nitroarenes adsorbed on the surface of the catalysts to generate the corresponding aromatic amines. Moreover, the catalyst showed excellent durability and reusability without obvious decrease in activity even after five reaction cycles. Thus, the study reported herein provides a cost-effective, sustainable strategy for fabrication of biomass-derived non-noble metal-based catalysts for green and efficient catalytic transformations.

Catalytic Materials Based on Surface Coating with Poly(ethyleneimine)-Stabilized Gold Nanoparticles

Ortega-Mu?oz, Mariano,Blanco, Victor,Hernandez-Mateo, Fernando,Lopez-Jaramillo, F. Javier,Santoyo-Gonzalez, Francisco

, p. 3965 - 3973 (2017/09/14)

Gold nanoparticles (AuNPs) can be obtained from HAuCl4 by using poly(ethyleneimine) (PEI) as both reductant and stabilizing agent. However, the known affinity of PEI for different materials has not been exploited to coat them and turn their surface catalytic. We demonstrate that the irradiation of a solution of HAuCl4 and branched PEI 1800 (bPEI2K) with microwave (MW) yields PEI-stabilized AuNPs (MW-PEI@AuNPs) with an average size of 7.6 nm that are catalytically active in the reduction with NaBH4 of different nitroarenes functionalized with a variety of functional groups. Moreover, the as-prepared MW-PE@-AuNPs show affinity for different materials such as polystyrene (standard spectrophotometry disposal cuvettes), polypropylene (Falcon-type tubes), and silica (Silica gel 60), turning their surface catalytic without any additional synthetic step. This feature was exploited to transform standard tubing (Tygon, poly(ether ether ketone), and stainless steel) into flow reactors by simple passage of a solution of MW-PEI@AuNPs. This straightforward functionalization is especially appealing in the case of the stainless-steel tubing, one of the materials more widely used in HPLC, which is of interest for flow nanocatalysis.

Platinum nanoparticles onto pegylated poly(lactic acid) stereocomplex for highly selective hydrogenation of aromatic nitrocompounds to anilines

Oberhauser, Werner,Evangelisti, Claudio,Tiozzo, Cristina,Bartoli, Mattia,Frediani, Marco,Passaglia, Elisa,Rosi, Luca

, p. 50 - 58 (2017/03/16)

A stereocomplexed poly(lactic acid)-polyethyleneglycol copolymer was synthesized and successfully used as recyclable support for Pt nanoparticles, generated by the metal vapor synthesis technique. The confinement of the Pt nanoparticles were determined by thermal analysis. Hydrogenation reactions of chlorinated aromatic nitro compounds, containing other reducible functional groups, to the corresponding anilines occurred with the latter supported Pt nanoparticles in MeOH under very mild reaction conditions (i.e. 30?°C, p(H2)?=?5.0?bar). The covalently attached polyethyleneglycol polymer significantly increased the catalytic activity of the supported Pt nanoparticles compared to an analogous catalytic system which did not contain polyethyleneglycol but the same sized Pt nanoparticles.

Structure and Catalytic Activity of Cr-Doped BaTiO3 Nanocatalysts Synthesized by Conventional Oxalate and Microwave Assisted Hydrothermal Methods

Srilakshmi, Chilukoti,Saraf, Rohit,Prashanth,Rao, G. Mohan,Shivakumara

, p. 4795 - 4805 (2016/06/09)

In the present study synthesis of BaTi1-xCrxO3 nanocatalysts (x = 0.0 ≤ x ≤ 0.05) by conventional oxalate and microwave assisted hydrothermal synthesis methods was carried out to investigate the effect of synthesis methods on the physicochemical and catalytic properties of nanocatalysts. These catalysts were thoroughly characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), N2 physisortion, and total acidity by pyridine adsorption method. Their catalytic performance was evaluated for the reduction of nitrobenzene using hydrazine hydrate as the hydrogen source. Structural parameters refined by Rietveld analysis using XRD powder data indicate that BaTi1-xCrxO3 conventional catalysts were crystallized in the tetragonal BaTiO3 structure with space group P4mm, and microwave catalysts crystallized in pure cubic BaTiO3 structure with space group Pm3μm. TEM analysis of the catalysts reveal spherical morphology of the particles, and these are uniformly dispersed in microwave catalysts whereas agglomeration of the particles was observed in conventional catalysts. Particle size of the microwave catalysts is found to be 20-35 nm compared to conventional catalysts (30-48 nm). XPS studies reveal that Cr is present in the 3+ and 6+ mixed valence state in all the catalysts. Microwave synthesized catalysts showed a 4-10-fold increase in surface area and pore volume compared to conventional catalysts. Acidity of the BaTiO3 catalysts improved with Cr dopant in the catalysts, and this could be due to an increase in the number of Lewis acid sites with an increase in Cr content of all the catalysts. Catalytic reduction of nitrobenzene to aniline studies reveals that BaTiO3 synthesized by microwave is very active and showed 99.3% nitrobenzene conversion with 98.2% aniline yield. The presence of Cr in the catalysts facilitates a faster reduction reaction in all the catalysts, and its effect is particularly notable in conventional synthesized catalysts.

Gold supported on titania for specific monohydrogenation of dinitroaromatics in the liquid phase

Liu, Shuang-Shuang,Liu, Xiang,Yu, Lei,Liu, Yong-Mei,He, He-Yong,Cao, Yong

, p. 4162 - 4169 (2014/09/29)

Liquid-phase selective monohydrogenation of various substituted dinitroaromatics to the corresponding valuable nitroanilines was investigated on gold-based catalysts. Special attention was paid to the effect of Au particle size on this monoreduction reaction. Interestingly, TiO2 supported gold catalysts containing a relatively larger mean Au particle size (>5 nm) showed far superior chemoselectivity for specific mono-hydrogenation of dinitroaromatics, with the highest performance attainable for the catalyst bearing Au particles of ca. 7.5 nm. Results in the intermolecular competitive hydrogenation showed that the intrinsic higher accumulation rates of the desired nitroanilines associated with the catalyst possessing larger Au particles were responsible for the high chemoselectivity observed. the Partner Organisations 2014.

Perovskite-type ferromagnetic BiFeO3 nanopowder: A new magnetically recoverable heterogeneous nanocatalyst for efficient and selective transfer hydrogenation of aromatic nitro compounds into aromatic amines under microwave heating

Farhadi,Rashidi

, p. 1021 - 1031 (2013/02/23)

Perovskite-type ferromagnetic BiFeO3 nanopowder was readily synthesized via thermal decomposition of Bi[Fe(CN)6].5H2O complex and characterized using thermal analysis (TGA/DSC), X-ray diffraction (XRD), Fourier-transformed infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), magnetic measurement and Brunauer-Emmett- Teller (BET) specific surface area measurements. The magnetic measurements show a ferromagnetic behavior for the BiFeO3 nanoparticles at room temperature. This nanosized ferromagnetic oxide with an average particle size of approximately 20 nm and a specific surface area of 48.5 m2/g was used as a new magnetically recoverable heterogeneous nanocatalyst for the highly efficient and selective reduction of aromatic nitro compounds into their corresponding amines by using propan-2-ol as the hydrogen donor under microwave irradiation. This method is regio- and chemoselective, clean, inexpensive and compatible with the substrates having hydrogenlyzable or reducible functional groups. As compared with conventional heating, this method is very fast and suitable for the large-scale preparation of different substituted anilines as well as other arylamines. The catalyst can also be reused without loss of activity. Iranian Chemical Society 2012.

Perovskite-type LaFeO3 nanoparticles prepared by thermal decomposition of the La[Fe(CN)6]·5H2O complex: A new reusable catalyst for rapid and efficient reduction of aromatic nitro compounds to arylamines with propan-2-ol under microwave irradiation

Farhadi, Saeid,Siadatnasab, Firouzeh

experimental part, p. 108 - 116 (2011/05/19)

Perovskite-type LaFeO3 nanoparticles were readily synthesized via thermal decomposition of the La[Fe(CN)6]·5H2O complex and characterized by using thermal analysis (TGA), X-ray diffraction (XRD), Fourier-transformed infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM) and BET specific surface area measurement. This nanosized perovskite-type oxide with an average particle size of 35 nm and a specific surface area 38.5 m2/g was used as a new reusable heterogeneous catalyst for highly efficient and selective reduction of aromatic nitro compounds into their corresponding amines by using propan-2-ol as the hydrogen donor under microwave irradiation. This method is regio- and chemoselective, clean, inexpensive and compatible with the substrates having hydrogenlysable or reducible functional groups. As compared with conventional heating, this method is very fast and suitable for large scale preparation of different substituted anilines as well as other arylamines. The catalyst can also be reused without observable loss of its activity.

Microwave-assisted rapid and efficient reduction of aromatic nitro compounds to amines with propan-2-ol over Nanosized perovskite-type SmFeO 3 powder as a new recyclable heterogeneous catalyst

Farhadi, Saeid,Siadatnasab, Firouzeh,Kazem, Maryam

experimental part, p. 104 - 108 (2011/06/27)

Nanosized perovskite-type SmFeO3 powder, prepared through the thermal decomposition of Sm[Fe(CN)6].4H2O with an average particle diameter of 28 nm and a specific surface area of 42 m2 g-1, was used as a recyclable heterogeneous catalyst for the efficient and selective reduction of aromatic nitro compounds into the corresponding amines by using propan-2-ol as a hydrogen donor (reducing agent) and KOH as a promoter under microwave irradiation. This highly regio-and chemoselective catalytic method is fast, clean, inexpensive, high yielding and also compatible with the substrates containing easily reducible functional groups. In addition, the nanosized SmFeO3 catalyst can be reused without loss of activity.

Highly chemo-and regioselective transfer reduction of aromatic nitro compounds using ammonium formate catalyzed by supported gold nanoparticles

Lou, Xia-Bing,He, Lin,Qian, Yue,Liu, Yong-Mei,Cao, Yong,Fan, Kang-Nian

supporting information; experimental part, p. 281 - 286 (2011/04/16)

A highly chemo-and regioselective reduction of a wide diversity of aromatic nitro compounds to the corresponding amines has been achieved by a combination of gold nanoparticles supported on titania and ammonium formate (HCOONH 4) in ethanol at room temperature. Furthermore, a direct and mild route to formanilides from aromatic nitro compounds bearing different functional groups by reductive N-formylation using the gold-mediated transfer reduction protocol is also established.

NiO nanoparticles prepared via thermal decomposition of the bis(dimethylglyoximato)nickel(II) complex: A novel reusable heterogeneous catalyst for fast and efficient microwave-assisted reduction of nitroarenes with ethanol

Farhadi, Saeid,Kazem, Maryam,Siadatnasab, Firouzeh

scheme or table, p. 606 - 613 (2011/04/16)

NiO nanoparticles with an average size of 12 nm and a high specific surface area of 88.5 m2/g were easily prepared via the thermal decomposition of the complex Ni(dmgH)2 and were characterized by TGA, XRD, FT-IR, TEM and BET surface area measurement. This nanosized transition metal oxide was used as a new heterogeneous catalyst for the reduction of nitroarenes under microwave irradiation. The efficient and selective reduction of aromatic nitro compounds into their corresponding amines was observed by using ethanol as a hydrogen donor (reducing agent) and KOH as a promoter under microwave irradiation. This highly regio-and chemoselective method is fast, simple, inexpensive, high yielding, clean and compatible with several sensitive functionalities, such as halogens,-OH,-OCH3,-CHO,-COCH 3,-COOH,-COOEt,-CONH2,-CN,-CHCH2 and-NHCOCH3. This method is suitable for the large scale preparation of different substituted anilines as well as other arylamines. In addition, the catalytic activity of nanosized NiO is higher than that of the bulk sample.

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