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2-Nitroaniline 88-74-4CAS NO.: 88-74-4
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2-Nitroaniline
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88-74-4 Usage

General Description

Orange solid with a musty odor. Sinks and mixes slowly with water.

Safety Profile

A poison. Moderately toxic by ingestion. Mildly toxic by skin contact. Mutation data reported. Mixtures with magnesium are hypergolic on contact with nitric acid. Forms extremely explosive addltion compounds with hexanitroethane. Vigorous reaction with sulfuric acid above 200°C. When heated to decomposition it emits toxic fumes of NOx. See also m- NITROANILINE, p-NITROANILINE, and ANILINE DYES.

Purification Methods

Crystallise the aniline from hot water (charcoal), then from aqueous 50% EtOH, or EtOH, and dry it in a vacuum desiccator. It has also been chromatographed on alumina, then recrystallised from *benzene. [Beilstein 12 IV 1563.]

Reactivity Profile

2-Nitroaniline may be sensitive to prolonged exposure to light. Mixtures of 2-Nitroaniline with magnesium are hypergolic on contact with nitric acid. 2-Nitroaniline forms extremely explosive addition compounds with hexanitroethane. 2-Nitroaniline has a vigorous reaction with sulfuric acid above 392° F. 2-Nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.

Hazard

Explosion risk. Toxic when absorbed by skin.

Environmental fate

Biological. Under aerobic and anaerobic conditions using a sewage inoculum, 2-nitroaniline degraded to 2-methylbenzimidazole and 2-nitroacetanilide (Hallas and Alexander, 1983). A Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 2-nitroaniline as the sole source of carbon. However, in the presence of 4-nitroaniline, approximately 50% of the applied 2-nitroaniline metabolized to nonvolatile products which could not be identified by HPLC (Zeyer and Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976). Plant. 2-Nitroaniline was degraded by tomato cell suspension cultures (Lycopericon lycopersicum). Transformation products identified were 2-nitroanilino-β-D-glucopyranoside, β-(2- amino-3-nitrophenyl)glucopyranoside, and β-(4-amino-3-nitrophenyl)-glucopyranoside (Pogány et al., 1990).

Health Hazard

Inhalation or ingestion causes headache, nausea, methemo- globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

Uses

Dyestuff intermediate.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5688, 1955 DOI: 10.1021/ja01626a066Organic Syntheses, Coll. Vol. 1, p. 388, 1941

Air & Water Reactions

Insoluble in water.

Chemical Properties

orange solid

88-74-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A11055)  2-Nitroaniline, 98%    88-74-4 250g 185.0CNY Detail
Alfa Aesar (A11055)  2-Nitroaniline, 98%    88-74-4 1000g 573.0CNY Detail
Alfa Aesar (A11055)  2-Nitroaniline, 98%    88-74-4 5000g 2284.0CNY Detail
Fluka (72660)  2-Nitroaniline  indicator (in nonaqueous solvents), ≥99.0% 88-74-4 72660-100G 1,199.25CNY Detail
Aldrich (N9780)  2-Nitroaniline  98% 88-74-4 N9780-500MG 134.55CNY Detail
Aldrich (N9780)  2-Nitroaniline  98% 88-74-4 N9780-5G 296.01CNY Detail
Aldrich (N9780)  2-Nitroaniline  98% 88-74-4 N9780-100G 270.27CNY Detail
Aldrich (N9780)  2-Nitroaniline  98% 88-74-4 N9780-500G 5,090.67CNY Detail

88-74-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-nitroaniline

1.2 Other means of identification

Product number -
Other names o-Nitraniline

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:88-74-4 SDS

88-74-4Synthetic route

benzofurazan oxide
480-96-6

benzofurazan oxide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With iron(II) sulfate In water; dimethyl sulfoxide Ambient temperature;100%
With HbO2(2+) In phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4;89 % Chromat.
4-methyl-N-(2-nitrophenyl)benzene sulfonamide
6380-13-8

4-methyl-N-(2-nitrophenyl)benzene sulfonamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 5.5h; Inert atmosphere;99%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr;98.6%
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr;98%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;95%
1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With hydrogen at 20℃; under 760.051 Torr; for 1h;98%
With hydrogen; 1-(2-benzimidazolyl)-C(CH3)=NH-NHCSNH2-Pd(II) In tetrahydrofuran at 20℃; for 2h; atmospheric pressure;95%
With triethylamine In water at 80℃; for 2h; Inert atmosphere; Green chemistry; chemoselective reaction;95%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction;97%
With sodium azide; chloroform; sulfuric acid
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 2h, reflux; Yield given. Multistep reaction;
o-nitroacetanilide
552-32-9

o-nitroacetanilide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;95%
With sodium hydroxide In ethanol Reflux;80%
With hydrogenchloride; water for 2h; Reflux;77%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 6h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;95%
Stage #1: 2-nitrophenyl bromide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 24h;
83%
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 70℃; for 24h;78%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Reagent/catalyst;95%
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 20h; pH=11; Green chemistry;86%
With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃;75%
With sodium peroxide
palladium-carbon In triethylene glycol dimethyl ether
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 4h; Catalytic behavior; Reagent/catalyst; Irradiation; chemoselective reaction;
95%
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Heating;94%
Stage #1: o-azidonitrobenzene 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 5h; Inert atmosphere; chemoselective reaction;
94%
N-(2-nitrophenyl)benzanilide
728-90-5

N-(2-nitrophenyl)benzanilide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;95%
With lithium aluminium tetrahydride In diethyl ether at 27℃; for 1h;66 % Turnov.
2-(2-nitrophenoxy)propanamide
58562-47-3

2-(2-nitrophenoxy)propanamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry;95%
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Reagent/catalyst; Smiles Aromatic Rearrangement;92%
With ammonia; water at 160 - 170℃;
With sodium tetrahydroborate In water at 20℃;
2-nitroaniline-4-sulfonic acid
616-84-2

2-nitroaniline-4-sulfonic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With phosphoric acid In sulfolane at 120℃; Reagent/catalyst; Solvent; Temperature;91%
With hydrogenchloride at 170 - 180℃; Erhitzen des Kaliumsalzes;
With sulfuric acid; water
aniline
62-53-3

aniline

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h;A 88%
B 12%
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite In neat (no solvent) for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation;A 86%
B n/a
With Iron(III) nitrate nonahydrate at 84.84℃; for 0.25h; regioselective reaction;A 77%
B 23%
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;87%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 6h; Sealed tube; Inert atmosphere;84%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;82%
2-(trimethylsilanyl)ethanesulfonic acid (2-nitrophenyl)amide
1045771-53-6

2-(trimethylsilanyl)ethanesulfonic acid (2-nitrophenyl)amide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 130℃; for 36h;87%
1-(2-chlorophenyl)-N-(2-nitrophenyl)-1H-tetrazol-5-amine

1-(2-chlorophenyl)-N-(2-nitrophenyl)-1H-tetrazol-5-amine

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h;84%
4-tert-butyl-2-(2-nitrophenylazo)phenol
27959-42-8

4-tert-butyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

N-formyldiethylamine
617-84-5

N-formyldiethylamine

C

2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole
3147-76-0

2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole

D

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;A n/a
B n/a
C 63%
D 82%
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

5-methylbenzo[d]oxazol-2(3H)-one
22876-15-9

5-methylbenzo[d]oxazol-2(3H)-one

C

2-nitro-aniline
88-74-4

2-nitro-aniline

D

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;A n/a
B n/a
C 7%
D 82%
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

(3R,4S)-2,3,4,5-Tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole
55520-53-1, 55520-54-2

(3R,4S)-2,3,4,5-Tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole

A

2-nitro-aniline
88-74-4

2-nitro-aniline

2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide
51849-78-6, 51849-79-7, 64057-39-2, 64057-40-5

2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide

C

C32H27N4O3P

C32H27N4O3P

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;A 20%
B n/a
C 80%
benzofurazan oxide
480-96-6

benzofurazan oxide

thiophenol
108-98-5

thiophenol

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

N-(2-nitrophenyl)benzensulphenamide

N-(2-nitrophenyl)benzensulphenamide

Conditions
ConditionsYield
With iron(II) sulfate In water; dimethyl sulfoxide for 1.5h; Ambient temperature;A 80%
B 20%
2-[(2-nitrophenyl)amino]ethanol
4926-55-0

2-[(2-nitrophenyl)amino]ethanol

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 144h;80%
4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With hydrogen bromide; acetic acid; aniline for 19h; Heating;80%
With sodium acetate In ethanol at 30℃; under 600 Torr; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere;74.6%
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 4h; Irradiation;
A 20%
B 80%
1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
Stage #1: 1,2-Dinitrobenzene With sodium tetrahydroborate In water at 20℃; for 0.25h; Inert atmosphere; Green chemistry;
Stage #2: In water at 20℃; for 0.75h; Inert atmosphere; Green chemistry;
A 78%
B 15%
With sodium tetrahydroborate; water at 0 - 20℃; for 24h;A 24%
B 53%
With titanium dioxide In ethanol for 1.5h; Irradiation; Green chemistry;A 55 %Chromat.
B 30 %Chromat.
ammonium hydroxide
1336-21-6

ammonium hydroxide

o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry;78%
N-(2-nitrophenyl)-1-phenyl-1H-tetrazol-5-amine

N-(2-nitrophenyl)-1-phenyl-1H-tetrazol-5-amine

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h;78%
2-nitrobenzamide
610-15-1

2-nitrobenzamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 1h;76%
nitrobenzene
98-95-3

nitrobenzene

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Product distribution; Mechanism; other sulfenamide reagents, other nitroarenes;A 71%
B 14%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;A 71%
B 14%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;A 71%
B 14%
phthalic anhydride
85-44-9

phthalic anhydride

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(o-nitrophenyl)phthalimide
34442-94-9

N-(o-nitrophenyl)phthalimide

Conditions
ConditionsYield
In acetic acid at 20℃; for 36h; Heating / reflux;100%
With acetic acid for 24h; Heating;89%
With N,N-dimethyl-formamide for 0.0666667h; microwave irradiation;84%
2-nitro-aniline
88-74-4

2-nitro-aniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-methyl-N-(2-nitrophenyl)benzene sulfonamide
6380-13-8

4-methyl-N-(2-nitrophenyl)benzene sulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With pyridine In dichloromethane at 20℃; for 48h;90%
With pyridine In dichloromethane at 20℃; for 16h;75%
2-nitro-aniline
88-74-4

2-nitro-aniline

4-iodo-2-nitroaniline
20691-72-9

4-iodo-2-nitroaniline

Conditions
ConditionsYield
With N-iodo-succinimide In acetic acid at 95℃; for 1h;100%
With sodium periodate; potassium iodide; sodium chloride In water; acetic acid at 25℃; for 8h;98%
With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 4h; Reagent/catalyst;98%
2-nitro-aniline
88-74-4

2-nitro-aniline

2-nitrobenzenediazonium tetrafluoroborate
365-33-3

2-nitrobenzenediazonium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With boron trifluoride diethyl etherate In dichloromethane at -15℃; for 0.25h;
Stage #2: With tert.-butylnitrite In dichloromethane at -15 - 0℃; for 1h;
100%
With tert.-butylnitrite; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;95%
With dinitrogen tetraoxide; benzene entsteht das Nitrat;
2-nitro-aniline
88-74-4

2-nitro-aniline

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With hydrazine hydrate at 90℃; for 1.16667h; chemoselective reaction;100%
With hydrazine hydrate In ethanol; water at 80℃; for 3h; chemoselective reaction;100%
With sodium tetrahydroborate In water for 0.116667h; Kinetics; Catalytic behavior; Reagent/catalyst;100%
cyanoacetic acid
372-09-8

cyanoacetic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

2-cyano-N-[2-(nitro)phenyl]acetamide
65372-22-7

2-cyano-N-[2-(nitro)phenyl]acetamide

Conditions
ConditionsYield
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux;
Stage #2: 2-nitro-aniline In dichloromethane for 2h; Reflux;
100%
With dicyclohexyldiimide In N,N-dimethyl-formamide for 1h; Ambient temperature;74%
With phosphorus pentachloride In benzene
methyl trans-3-(4-methoxyphenyl)glycidate
96125-49-4

methyl trans-3-(4-methoxyphenyl)glycidate

2-nitro-aniline
88-74-4

2-nitro-aniline

2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylamino)-propionic acid methyl ester
100597-06-6, 100597-07-7

2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylamino)-propionic acid methyl ester

Conditions
ConditionsYield
zinc(II) iodide In toluene at 22℃; for 21h; Product distribution; various solvents, additives, temperatures, times;100%
zinc(II) iodide In toluene at 22℃; for 21h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-nitro-aniline
88-74-4

2-nitro-aniline

(2-nitro-phenyl)-carbamic acid tert-butyl ester
54614-93-6

(2-nitro-phenyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 1h;
100%
With 12-TPA/SBA 15 at 20℃; for 0.1h; Neat (no solvent);97%
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 2h;
96%
2-nitro-aniline
88-74-4

2-nitro-aniline

p-tert-butyl benzoyl chloride
1710-98-1

p-tert-butyl benzoyl chloride

N-(2-nitrophenyl)-4-(1,1-dimethylethyl)-benzamide
219492-27-0

N-(2-nitrophenyl)-4-(1,1-dimethylethyl)-benzamide

Conditions
ConditionsYield
With pyridine Acylation;100%
With pyridine In dichloromethane Acylation;
acetic acid
64-19-7

acetic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

Conditions
ConditionsYield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;100%
With hydrogenchloride; iron In water at 70 - 100℃;
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine
74002-26-9

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 24h; Buchwald-Hartwig coupling; Inert atmosphere;100%
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Buchwald-Hartwig reaction;99%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; Inert atmosphere;86%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 30h;65%
2-nitro-aniline
88-74-4

2-nitro-aniline

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-Trifluoromethylbenzimidazole
312-73-2

2-Trifluoromethylbenzimidazole

Conditions
ConditionsYield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-nitro-aniline
88-74-4

2-nitro-aniline

2-nitrophenyl isocyanate
3320-86-3

2-nitrophenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In toluene for 3h; Heating;
In dichloromethane at 0℃; for 0.5h;
Cyclopentane
287-92-3

Cyclopentane

carbon monoxide
201230-82-2

carbon monoxide

2-nitro-aniline
88-74-4

2-nitro-aniline

C6H9ONHC6H4NO2

C6H9ONHC6H4NO2

Conditions
ConditionsYield
With aluminum tri-bromide at -20℃;100%
Stage #1: Cyclopentane; carbon monoxide With aluminum tri-bromide; carbon tetrabromide In various solvent(s) at 0℃; under 760.051 Torr; for 4h;
Stage #2: 2-nitro-aniline In various solvent(s) at -20 - 20℃; under 760.051 Torr; Further stages.;
100 % Chromat.
Stage #1: Cyclopentane; carbon monoxide With 2AlBr3*CBr4 In dibromomethane
Stage #2: 2-nitro-aniline In dibromomethane at 0℃; for 2h; chemoselective reaction;
97 %Chromat.
2-thienylacetic acid chloride
39098-97-0

2-thienylacetic acid chloride

2-nitro-aniline
88-74-4

2-nitro-aniline

C12H10N2O3S

C12H10N2O3S

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

2-nitro-aniline
88-74-4

2-nitro-aniline

2,2-dimethyl-5-((2-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione
25063-47-2

2,2-dimethyl-5-((2-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
2-nitro-aniline
88-74-4

2-nitro-aniline

benzyl alcohol
100-51-6

benzyl alcohol

2-phenyl-1H-benzoimidazole
716-79-0

2-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With palladium with copper supported on alumina In water at 179.84℃; under 26252.6 Torr; for 12h; Autoclave;100%
With JRC-TIO-7-supported iridium catalyst In 1,3,5-trimethyl-benzene at 80℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 160℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;97%
2-nitro-aniline
88-74-4

2-nitro-aniline

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

C12H12N2O6

C12H12N2O6

Conditions
ConditionsYield
at 20℃; for 0.133333h; Milling; Inert atmosphere;100%
2-nitro-aniline
88-74-4

2-nitro-aniline

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry;99.2%
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction;85%
With N-chloro-succinimide In acetonitrile for 10h; Heating;57%
Multi-step reaction with 2 steps
1: diethyl ether; hypochlorous acid / 20 °C
2: hydrochloric acid; diethyl ether / -20 °C
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(2-nitrophenyl)benzanilide
728-90-5

N-(2-nitrophenyl)benzanilide

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 18h;99%
With pyridine at 25℃; for 15h;97%
With pyridine; dmap93%
2-nitro-aniline
88-74-4

2-nitro-aniline

acetyl chloride
75-36-5

acetyl chloride

o-nitroacetanilide
552-32-9

o-nitroacetanilide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;99%
With montmorillonite K-10 In dichloromethane for 1.5h; Ambient temperature;98%
With carbon-silica composite from starch (7.5 molpercent SO3H) at 60℃; for 0.75h; solvent-free conditions;95%
2-nitro-aniline
88-74-4

2-nitro-aniline

4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In methanol at 0 - 20℃; for 12h;99%
With HMTAB In dichloromethane at 20℃; for 0.5h;98%
With 1-butyl-3-methylpyridinium tribromide at 20℃;98%
2-nitro-aniline
88-74-4

2-nitro-aniline

2,4-dibromo-6-nitroaniline
827-23-6

2,4-dibromo-6-nitroaniline

Conditions
ConditionsYield
With bromine In methanol; dichloromethane at 20℃; for 1h;99%
With bromine; acetic acid at 45℃; for 4h;98%
With bromine; acetic acid at 45℃; for 4h;98%
3-methylbutyric acid trimethylsilyl ester
55557-13-6

3-methylbutyric acid trimethylsilyl ester

2-nitro-aniline
88-74-4

2-nitro-aniline

3-methyl-2'-nitrobutananilide
150783-30-5

3-methyl-2'-nitrobutananilide

Conditions
ConditionsYield
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-nitro-aniline
88-74-4

2-nitro-aniline

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

bis(2-nitrophenyl)amine
18264-71-6

bis(2-nitrophenyl)amine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h;99%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h; Inert atmosphere;95%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 20h; Inert atmosphere; Schlenk technique;94%
2-nitro-aniline
88-74-4

2-nitro-aniline

acetylacetone
123-54-6

acetylacetone

3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione
24756-10-3

3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite
Stage #2: acetylacetone With sodium hydroxide; sodium acetate In methanol; water at 0 - 20℃; for 1h; Further stages.;
99%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: acetylacetone With sodium acetate In methanol; water at 20℃;
87%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium hydroxide; sodium nitrite In water at -0.16℃;
Stage #2: acetylacetone In water at -0.16℃; for 1h;
79%
With hydrogenchloride; sodium acetate; sodium nitrite 1.) water, 0 deg C, 2.) acetone, 6 h; Multistep reaction;
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite at 0℃; for 0.5h;
Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 3h; Further stages.;
2-nitro-aniline
88-74-4

2-nitro-aniline

β-naphthol
135-19-3

β-naphthol

1-[(2-nitrophenyl)azo]-2-naphthalenol
6410-09-9

1-[(2-nitrophenyl)azo]-2-naphthalenol

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With sulfuric acid; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: β-naphthol In water at 20℃; for 2h;
99%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 4.25h;
Stage #2: With aminosulfonic acid In water at 0℃; for 1h;
Stage #3: β-naphthol In ethanol; water at 20℃; for 19.5h;
93%
Stage #1: 2-nitro-aniline With sodium nitrite In water at 20℃; Milling; Green chemistry;
Stage #2: β-naphthol In water at 20℃; for 0.5h; Milling; Green chemistry;
83%
2-nitro-aniline
88-74-4

2-nitro-aniline

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

(E)-methyl 2-nitrocinnamate
39228-29-0

(E)-methyl 2-nitrocinnamate

Conditions
ConditionsYield
With tert.-butylnitrite; methanesulfonic acid; palladium diacetate; methoxybenzene In methanol at 0 - 25℃; for 48h; Reagent/catalyst; Heck Reaction;99%
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h;
Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; Heck-Matsuda reaction;
98%
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Heck-Matsuda reaction;
Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; for 48h; Heck-Matsuda reaction;
98%
benzaldehyde
100-52-7

benzaldehyde

2-nitro-aniline
88-74-4

2-nitro-aniline

2-phenyl-1H-benzoimidazole
716-79-0

2-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With hydrogen In ethyl acetate at 20℃; under 7500.75 Torr; for 20h; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature; Autoclave; Green chemistry;99%
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Reagent/catalyst; Solvent; Pressure; Time; Temperature;99%
Stage #1: benzaldehyde; 2-nitro-aniline In 1,4-dioxane; water at 90℃; for 0.0833333h;
Stage #2: With formic acid In 1,4-dioxane; water at 90℃; for 8h; Temperature; Sealed tube;
96%

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