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88-73-3

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88-73-3 Usage

Chemical Properties

yellow solid with a characteristic odour

Uses

Different sources of media describe the Uses of 88-73-3 differently. You can refer to the following data:
1. Intermediate, especially for dyes.
2. Chemical intermediate in manufacture of dyes, picric acid, lumber preservatives, and diaminophenol hydrochloride (a photographic developer)
3. 1-Chloro-2-nitrobenzene was used in the synthesis of 1-hydroxybenzotriazole derivatives. It is important as a precursor to other compounds due to the two reactive sites present on the molecule.

General Description

Yellow crystals with an aromatic odor. Sinks in water.

Air & Water Reactions

2-Nitrochlorobenzene may be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

O-NITROCHLOROBENZENE is incompatible with strong bases and strong oxidizing agents. 2-Nitrochlorobenzene will react with ammonia.

Health Hazard

INHALATION: Headache, languour, anemia. Irritation of nose and throat, cyanosis, shallow respiration, convulsions, and coma. EYES: Irritation. SKIN: Irritation. INGESTION: Forms methemoglobin giving rise to cyanosis and blood changes.

Flammability and Explosibility

Notclassified

Safety Profile

Suspected carcinogen with experimental carcinogenic and neoplastigenic data. Poison by ingestion, skin contact, and probably inhalation. Combustible when exposed to heat or flame. To fight fire, use water, foam. Potentially explosive reaction with ammonia at 160℃/30 bar. When heated to decomposition it emits toxic fumes of Cl-, NOx, and phosgene. See also other chloronitrobenzene entries and NITRO COMPOUNDS of AROMATIC HYDROCARBONS.

Purification Methods

Crystallise it from EtOH, MeOH or pentane (charcoal). [Beilstein 5 IV 721.]

Check Digit Verification of cas no

The CAS Registry Mumber 88-73-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 88-73:
(4*8)+(3*8)+(2*7)+(1*3)=73
73 % 10 = 3
So 88-73-3 is a valid CAS Registry Number.

88-73-3SDS

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 2-Chloronitrobenzene

1.2 Other means of identification

Product number -
Other names 2-Nitrochlorobenzene

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:88-73-3 SDS

88-73-3Synthetic route

2-Chloroaniline
95-51-2

2-Chloroaniline

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux;78%
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 1h; pH=11; Green chemistry;78%
With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃;65%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With CuCl-alumina In various solvent(s) at 150℃; for 6h;75%
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 36h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;70%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With oxygen; silver carbonate; potassium hydroxide; copper dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130 - 140℃;83%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique;45%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique;45%
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube;35%
2-Chlorobenzeneboronic acid
3900-89-8

2-Chlorobenzeneboronic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With zirconium(IV) oxynitrate hydrate; iodine In toluene at 20℃; for 16h; Inert atmosphere;84%
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere;70%
With nitric acid; trifluoroacetic acid In water at 80℃; for 18h; regioselective reaction;61%
2-nitro-aniline
88-74-4

2-nitro-aniline

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With p-toluenesulfonyl nitrite; copper dichloride In acetonitrile at 25℃; for 0.0166667h;87%
With hydrogenchloride; potassium nitrite; dimethyl sulfoxide In water at 35℃; for 0.5h;73%
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; 10-camphorsulfonic acid In neat (no solvent) Time; Solvent;59%
2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With ammonia at 125℃; under 15001.5 Torr; for 1h; Autoclave;99.85%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With bromine; iodine; chlorine at 140℃; for 2h; Reagent/catalyst; Temperature;86.1%
chlorobenzene
108-90-7

chlorobenzene

A

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

B

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

C

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With dinitrogen tetraoxide; N,N,N,N-tetraethylammonium tetrafluoroborate In sulfolane at 30℃; electrochemical process; Yield given. Yields of byproduct given;
With zeolite H-beta; Nitrogen dioxide at 150℃; Yield given. Yields of byproduct given;
With zeolite FeAl-ZSM-5; Nitrogen dioxide at 150℃; Yield given. Yields of byproduct given;
chlorobenzene
108-90-7

chlorobenzene

A

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

B

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;A 86%
B 14%
With ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating;A 82%
B 16%
With ammonium nitrate; trifluoroacetic anhydride at 25℃; for 2h;A 80%
B 20%
2-nitrobenzenediazonium o-benzenedisulfonamide

2-nitrobenzenediazonium o-benzenedisulfonamide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 60℃; for 0.75h; Substitution;77%
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution;74%
chlorobenzene
108-90-7

chlorobenzene

A

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

B

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

C

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

1-chloro-2,4-dinitro-benzene

Conditions
ConditionsYield
With nitric acid; acetic anhydride at 0 - 20℃; for 0.166667h; Overall yield = 76 %;
2-nitro-benzenediazonium acetate

2-nitro-benzenediazonium acetate

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With hydrogenchloride; copper(l) chloride at 0 - 5℃; oder bei 100-105grad;
<2-chloro-phenyl>-mercury acetate

<2-chloro-phenyl>-mercury acetate

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With nitric acid at 65℃;
1-(2-nitro-phenyl)-2-phenoxy-ethanol

1-(2-nitro-phenyl)-2-phenoxy-ethanol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 36h; Autoclave;62 %Chromat.
2-Nitrobenzyl alcohol
612-25-9

2-Nitrobenzyl alcohol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave;96 %Chromat.
2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave;95 %Chromat.
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Reagent/catalyst; Solvent; Time; Autoclave;87 %Chromat.
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Reagent/catalyst; Autoclave; Molecular sieve;84 %Chromat.
2-(1-Hydroxypropyl)nitrobenzene
90972-31-9

2-(1-Hydroxypropyl)nitrobenzene

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave;92 %Chromat.
2-bromo-1-(2-nitro-phenyl)-ethanol
88057-15-2

2-bromo-1-(2-nitro-phenyl)-ethanol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 36h; Autoclave;98 %Chromat.
chlorobenzene
108-90-7

chlorobenzene

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

A

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

B

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With gold at -256.16℃;
chlorobenzene
108-90-7

chlorobenzene

A

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

B

4-chloro-2,6-dinitrophenol
88-87-9

4-chloro-2,6-dinitrophenol

C

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

D

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With oxygen; Nitrogen dioxide; iron(III)-acetylacetonate In 1,2-dichloro-ethane at 0℃; for 36h; Yield given. Yields of byproduct given;
1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
Stage #1: 1,2-Dinitrobenzene With perchloric acid; sulfuric acid; sodium nitrite In water; ethyl acetate Electrochemical reaction;
Stage #2: With hydrogenchloride; copper In water Sandmeyer Reaction; Electrochemical reaction;
63%
2-chloro-benzenediazonium-(1)-tetrafluoroborate

2-chloro-benzenediazonium-(1)-tetrafluoroborate

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With water; copper; sodium nitrite
2-nitro-benzenediazonium-(1)-sulfate

2-nitro-benzenediazonium-(1)-sulfate

A

1-nitro-2-(2-nitrophenyl)benzene
2436-96-6

1-nitro-2-(2-nitrophenyl)benzene

B

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With hydrogen bromide; copper(l) chloride
aniline hydrochloride
142-04-1

aniline hydrochloride

A

2,4-dichloronitrobenzene
611-06-3

2,4-dichloronitrobenzene

B

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

C

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 20℃;A 12%
B 36%
C 23%
2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); copper acetylacetonate; copper(l) cyanide; sodium carbonate In 1,4-dioxane at 130℃; for 24h; Sealed tube; Air;
chlorobenzene
108-90-7

chlorobenzene

A

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

B

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With poly(4-vinylpyridine)-nitrating mixture complex In dichloromethane at 20℃; for 2h; Green chemistry; Overall yield = 81 %;
methoxybenzene
100-66-3

methoxybenzene

A

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

B

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

C

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

Conditions
ConditionsYield
With N-nitro-2,4,6-trimethylpyridinium tetrafluoroborate In nitromethane at 25℃; Rate constant; competitive nitration with benzene;
morpholine
110-91-8

morpholine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-(2-nitrophenyl)morpholine
5320-98-9

N-(2-nitrophenyl)morpholine

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;99%
With potassium phosphate; Al2O3#dotCo(2+) In water at 100℃; for 7h;90%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-Chloroaniline
95-51-2

2-Chloroaniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
With [1-butyl-2,3-dimethylimidazolium][tppm] stabilized rhodium nanoarticles at 50℃; under 22502.3 Torr; for 5h; Ionic liquid; Autoclave; chemoselective reaction;100%
With hydrogen at 50℃; under 22502.3 Torr; for 5h; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction;100%
pyrrolidine
123-75-1

pyrrolidine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-(2-nitrophenyl)pyrrolidine
40832-79-9

1-(2-nitrophenyl)pyrrolidine

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; under 6375510 Torr; for 20h;100%
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;100%
at 108℃; for 2h; Neat (no solvent);98%
dibromodifluoromethane
75-61-6

dibromodifluoromethane

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-nitrobenzotrifluoride
384-22-5

2-nitrobenzotrifluoride

Conditions
ConditionsYield
With ISOPROPYLAMIDE; copper at 100℃; for 16h;100%
With copper In N,N-dimethyl acetamide at 100℃; for 4h; Product distribution; with or without charcoal;89%
With copper; pyrographite In N,N-dimethyl acetamide at 100℃; for 2h;89 % Turnov.
With copper In N,N-dimethyl acetamide at 100℃; for 8h;59 % Chromat.
2,4-dimethyl-thiophenol
13616-82-5

2,4-dimethyl-thiophenol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2,4-dimethyl-1-[(2-nitro-phenyl)-sulfanyl]-benzene

2,4-dimethyl-1-[(2-nitro-phenyl)-sulfanyl]-benzene

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 50℃; for 5h;100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2.5h; Inert atmosphere;99.79%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;97%
3,5-Difluoro-4-methoxybenzylamine
105969-16-2

3,5-Difluoro-4-methoxybenzylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-(3,5-difluoro-4-methoxybenzyl)-2-nitroaniline
105969-11-7

N-(3,5-difluoro-4-methoxybenzyl)-2-nitroaniline

Conditions
ConditionsYield
With ammonium acetate at 100℃; for 24h;100%
acetic anhydride
108-24-7

acetic anhydride

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-(2-chlorophenyl)acetamide
533-17-5

N-(2-chlorophenyl)acetamide

Conditions
ConditionsYield
With indium; acetic acid In methanol at 20℃; for 1.5h;100%
With samarium; acetic acid In methanol at 20℃; for 1.5h;80%
With aluminum oxide; zinc In dichloromethane at 20℃; for 12h; Acetylation; reduction;75%
4-dibenzothiophene boronic acid
108847-20-7

4-dibenzothiophene boronic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

4-(2-nitrophenyl)dibenzo[b,d]thiophene
530403-00-0

4-(2-nitrophenyl)dibenzo[b,d]thiophene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; benzene at 70℃; for 7h;100%
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;87%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

dibenzoselenophene-4-boronic acid
530403-10-2

dibenzoselenophene-4-boronic acid

4-(2-nitrophenyl)dibenzoselenophene
530403-13-5

4-(2-nitrophenyl)dibenzoselenophene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; benzene at 70℃;100%
thiophenol
108-98-5

thiophenol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-nitrophenyl phenyl sulfide
4171-83-9

2-nitrophenyl phenyl sulfide

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide 1.) between -3 and +2 deg C, 40 min, 2.) 80 deg C, 1 h;99.9%
With C40H30Cl2N2NiO2S2; sodium hydroxide In N,N-dimethyl-formamide at 70℃; for 2h;96%
With potassium fluoride impregnated on clinoptilolite; air In dimethyl sulfoxide at 115 - 120℃; for 4h;95%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

methylamine
74-89-5

methylamine

2-nitro-N-methylaniline
612-28-2

2-nitro-N-methylaniline

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;99.3%
In water at 130℃; for 24h; Autoclave;99%
With copper In water at 100℃; for 8h; Sealed tube;95%
cyclohexylamine
108-91-8

cyclohexylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-cyclohexyl-2-nitroaniline
6373-71-3

N-cyclohexyl-2-nitroaniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;99%
With potassium carbonate; Cu/Al-HTB at 100℃; for 8h;91%
With 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide; caesium carbonate; copper(I) bromide at 115℃; for 24h; Inert atmosphere; Schlenk technique;81%
With ethanol at 150℃;
With potassium carbonate In dimethyl sulfoxide at 60℃; for 17h;
ethylamine
75-04-7

ethylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-Ethyl-2-nitroaniline
10112-15-9

N-Ethyl-2-nitroaniline

Conditions
ConditionsYield
In water at 105℃; for 24h; Sealed vessel;99%
In dimethyl sulfoxide85%
With ethanol at 170℃;
3-Pyrroline
109-96-6

3-Pyrroline

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-(2-Nitro-phenyl)-2,5-dihydro-1H-pyrrole
113342-92-0

1-(2-Nitro-phenyl)-2,5-dihydro-1H-pyrrole

Conditions
ConditionsYield
at 70℃; for 0.75h;99%
n-Dodecylamine
124-22-1

n-Dodecylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-Monododecyl-o-nitraniline
94208-22-7

N-Monododecyl-o-nitraniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;95%
In nitrobenzene at 190 - 200℃; for 6h;46%
n-Octylamine
111-86-4

n-Octylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-Monooctyl-o-nitraniline
22100-61-4

N-Monooctyl-o-nitraniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;99%
In nitrobenzene at 190 - 200℃; for 6h;64%
chloromethyl phenyl sulfone
7205-98-3

chloromethyl phenyl sulfone

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-benzenesulfonylmethyl-3-chloro-2-nitro-benzene
86434-29-9

1-benzenesulfonylmethyl-3-chloro-2-nitro-benzene

Conditions
ConditionsYield
With potassium tert-butylate; acetic acid In tetrahydrofuran at -50 - 20℃; for 0.5h;99%
α-phenoxy-α-phenylacetonitrile
32121-27-0

α-phenoxy-α-phenylacetonitrile

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

α-(3-Chloro-4-nitrophenyl)phenylacetonitrile
89278-13-7

α-(3-Chloro-4-nitrophenyl)phenylacetonitrile

Conditions
ConditionsYield
Stage #1: α-phenoxy-α-phenylacetonitrile; 2-Chloronitrobenzene With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -78℃; for 0.25h;
Stage #2: With hydrogenchloride In water at -78℃;
99%
With sodium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature;55%
3,5-difluorobenzylamine
90390-27-5

3,5-difluorobenzylamine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

N-(3,5-difluorobenzyl)-2-nitroaniline
105969-13-9

N-(3,5-difluorobenzyl)-2-nitroaniline

Conditions
ConditionsYield
With ammonium acetate at 100℃; for 24h;99%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

phenylboronic acid
98-80-6

phenylboronic acid

2-nitrobiphenyl
86-00-0

2-nitrobiphenyl

Conditions
ConditionsYield
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 1h; Suzuki-Miyaura coupling; Heating;99%
With C12H10N3OPol; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 100℃; for 15h; Suzuki-Miyaura reaction;99%
With potassium carbonate In water; isopropyl alcohol at 100℃; for 18h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere;99%
1H-imidazole
288-32-4

1H-imidazole

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-(2-nitrophenyl)-1H-imidazole
23309-16-2

1-(2-nitrophenyl)-1H-imidazole

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃;99%
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry;99%
With potassium carbonate; bis(μ-iodo)bis[(-)-sparteine]dicopper(I) In dimethyl sulfoxide at 125℃; for 12h;92%
trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

(E)-2-nitrostilbene
4264-29-3

(E)-2-nitrostilbene

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In 1,4-dioxane for 1h; Suzuki-Miyaura cross-coupling; Heating;99%
S-methyl-S-phenylsulfoximine
4381-25-3

S-methyl-S-phenylsulfoximine

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

rac-N-[2-(nitro)phenyl]-S-methyl-S-phenylsulfoximine

rac-N-[2-(nitro)phenyl]-S-methyl-S-phenylsulfoximine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos In toluene at 135℃; for 24h; Buchward-Hartwig coupling;99%
3-methyl-phenol
108-39-4

3-methyl-phenol

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-(3'-methylphenoxy)nitrobenzene
54495-62-4

2-(3'-methylphenoxy)nitrobenzene

Conditions
ConditionsYield
With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry;99%
Stage #1: 3-methyl-phenol With potassium hydroxide at 90℃; for 0.25h;
Stage #2: 2-Chloronitrobenzene at 150℃; for 2h;
formic acid
64-18-6

formic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-chloro-2-(dimethylamino)benzene
698-01-1

1-chloro-2-(dimethylamino)benzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)platinum; phenylsilane; C30H51Cl3Mo3N6PPtS4(1+)*BF4(1-) In tetrahydrofuran at 70℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
sodium methylate
124-41-4

sodium methylate

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-Nitroanisole
91-23-6

2-Nitroanisole

Conditions
ConditionsYield
In methanol at 48 - 65℃; for 1h; Temperature; Large scale;98.9%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

4'-chloro-2-nitrobiphenyl
6271-80-3

4'-chloro-2-nitrobiphenyl

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;98%
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling;98%
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling;98%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

bis(2-nitrophenyl)ether
2217-65-4

bis(2-nitrophenyl)ether

Conditions
ConditionsYield
With sodium ethanolate In methanol at 45 - 80℃; for 1.25h; Solvent; Temperature; Large scale;98.9%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; water; caesium carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(pinacol)diborane In N,N-dimethyl-formamide at 140℃; for 24h; Schlenk technique; chemoselective reaction;73%

88-73-3Relevant articles and documents

Nitration of deactivated aromatic compounds via mechanochemical reaction

Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin

supporting information, (2021/05/05)

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Synthesis method of metolachlor intermediate

-

Paragraph 0078-0084; 0097-0103, (2021/09/21)

The synthesis method comprises the following steps: S1) nitration reaction of chlorobenzene in a nitration reagent to obtain a mixture of o-chloronitrobenzene and p-chloronitrobenzene without separation. S2) The mixture of o-chloronitrobenzene and p-chloronitrobenzene is subjected to catalytic hydrogenation reaction to obtain the mixture of o-chloroaniline and p-chloroaniline, and the product does not need to be separated. S3) The mixture of o-chloroaniline and chloroaniline is subjected to diazotization reaction to obtain the mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine, and the product does not need to be separated. S4) The mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine and aldehyde are subjected to a condensation reaction to obtain a triazole ring mixture of Formulae I through a and I through b. S5) The triazole ring mixture is subjected to chlorination reaction to obtain the metolachlor intermediate shown in the formula I. 2, 4 - Dichloroaniline is used as a raw material, the production cost of the metolachlor is reduced, and the supply limitation of the raw material is avoided.

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi

, p. 18040 - 18049 (2021/05/29)

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.