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88-72-2

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88-72-2 Usage

Overview

O-nitrotoluene is also known as 2-nitrotoluene or 1-methyl-2-nitrobenzene,and is yellow oily transparent liquid. It has the smell of nitrobenzene. The relative density is 1.1629. The melting point is-2.9℃ (α-type, stable type),-9.5℃ (β-type, non-stable type). The boiling point is 221.7 °C, 118 °C (2.133×103Pa) and 50.0 °C (0.133×103Pa). The flash point is 106.1 °C (closed system). The refractive index is 1.5450. The viscosity is 0.0262 mPa?s (15℃). The vapor pressure (×103 Pa) is 10.906 (5℃), 12.639 (10℃), 14.612 (20℃), 15.892 (30℃). It is slightly soluble in water (0.061 at 30°C), soluble in benzene, chloroform and petroleum ether and immiscible with ethanol and ether. It can evaporate together with water vapor. Due to the strong electron-withdrawing ability of nitro group, the methyl of is easy to be oxidized to form o-nitrobenzaldehyde or o-nitrobenzoic acid according to oxidation conditions. And o-nitrotoluene can be reduced in the presence of catalyst to generate o-toluidine, which can generate 2,4 or 2,6 dinitrotoluene after further nitration. O-nitrotoluene can also be chlorinated to generate nitrobenzyl chloride. In addition, o-nitrotoluene can also generate azo compounds. LD50 (rat oral) is 801mg/kg. O-nitrotoluene is mainly used as the raw material of dyestuffs to prepare 4-chloro-2-nitrotoluene, 6-chloro-2-nitrotoluene, o-toluidine, o-tolidine, 2,6-dichlorobenzaldehyde and other dyestuffs intermediates, in which 4-chloro-2-nitrotoluene is a pharmaceutical raw material and o-toluidine is the raw material of pesticide fungicides and spices. O-nitrotoluene is a pharmaceutical raw material to prepare 2,2'-dinitrobenzene, o-nitrobenzyl bromide, bromine alkane and other medicines, and is also the raw material to prepare indole to be used as amino acids and plant growth regulators. O-nitrotoluene is the raw material to prepare dinitrotoluene to be used as powder. O-toluidine can also be used as vulcanization accelerator and to prepare o-nitrobenzoic acid as pharmaceutical raw material.

Chemical Properties

Different sources of media describe the Chemical Properties of 88-72-2 differently. You can refer to the following data:
1. Yellow flammable liquid; insoluble in water; soluble in chloroform and benzene; immiscible with ethanol and ethyl ether.
2. light yellow to darker yellow-green liquid

Application

Used for the intermediates of dyes and pesticides, and also for the production of coatings, plastics and pharmaceuticals. O-nitrotoluene is mainly used in the production of o-toluidine, o-tolidine, and also used as the important raw materials of dyes, paints, plastics and pharmaceutical. In the pharmaceutical industry, it is used for the production of nifedipine, tegretol, imipramine hydrochloride, bromide has hydrochloride amine and sodium dicloxaeillin.I can also be used for dyes, pharmaceuticals, pesticides, plastics and other industries.

Production method

Nitrify toluene with mixed acid to generate mixed nitrotoluene, which mainly consists of o-nitrotoluene (about two-thirds) and p-nitrotoluene (about one-third). The mixed nitrotoluene can be separated to get the pure product. Add toluene to the reactor and cool to below 25℃. Then add the mixed acid (ie, 25-30% of nitric acid, 55-58% of sulfuric acid and 20-21% of water) and control the temperature not exceeding 50℃. Stir for 1-2h, and then stand for 6h. Separate the generated nitrotoluene, and wash them with water and alkali liquor to remove unreacted toluene and aliphatic compound. The crude nitrotoluene products consist of 55-60% of o-nitrotoluene, 2-5% of m-nitrotoluene and 35-40% of p-nitrotoluene, with a yield of 90-95%. The various isomers can be separated by crude distillation and crystallization according to the difference of the boiling point and melting point. Namely, first distill the crude nitrotoluene under vacuum to separate out the majority of o-nitrotoluene. And then the residual fraction containing more p-nitrotoluene is separated by vacuum distillation, and cooled for crystallization and separated to obtain the finished products. The tarry substance with high boiling point remains in the still. M-nitrotoluene remains in the mother liquor separated out the p-nitrotoluene, and can be obtained by rectification after repeated accumulation. The purity of ortho and para nitrotoluene can respectively reach 98% and 99%. The domestic process is the two-pot series process, and the reaction temperature of the main pot is 40-45℃ and the second pot is 50-55℃. The preparation of mixed acid is roughly similar, including 26-28% of nitric acid, 56-57% of sulfuric acid and 16-18% of water. The raw material consumption quota: toluene (98%) 800kg/t, nitric acid (98%) 470kg/t, sulfuric acid (92.5%) 450kg/t, caustic soda (42%) 100kg /t

Description

o-Nitrotoluene is a yellow-coloured liquid. It is used for the synthesis of a variety of industrial products. These include to synthesise agricultural and rubber chemicals, azo and sulphur dyes, and dyes for cotton, wool, silk, leather, and paper. O-nitrotoluene decomposes on contact with strong oxidants, reducing agents, acids, or bases producing toxic fumes, nitrogen oxides, and carbon monoxide.

Physical properties

Clear, colorless to pale yellowish combustible liquid with a faint, aromatic odor. May darken on exposure to air.

Uses

Different sources of media describe the Uses of 88-72-2 differently. You can refer to the following data:
1. 2-Nitrotoluene is a nitroaromatic compound. It is used in the synthesis of intermediates for azo dyes, sulfur dyes, rubber chemicals, and agriculture chemicals; typical intermediates are o-toluidine, o-nitrobenzaldehyde, 2-nitro-4-chlorotoluene, 2-nitro-6-chlorotoluene, 2-amino-4-chlorotoluene (Fast Scarlet TR Base), and 2-amino-6-chlorotoluene (Fast Red KB Base).
2. 2-Nitrotoluene is used as an intermediate for the o-toludine synthesis, which finds application in the dyestuff industry. It is employed as a reagent in detecting and photometric determining oxidizing agent. It is also used in the determination of prussic acid content in the air. It acts as a precursor to prepare 2-amino-4-chlorotoluene, 2-amino-6-chlorotoluene, nitrotoluenesulfonic acids and toluene nitrosulfonic chlorides. It acts as a nitrogen supplement in the culture medium of pseudomonas sp. strain ClS1. It acts as a carbon and energy supplement in the culture medium of Pseudomonas sp. strain JS42.

Preparation

2-Nitrotoluene was synthesized by nitration of toluene with mixed acid, A mixture of mononitrotoluene isomers can be prepared from the nitration of toluene between -10 oC and 30 oC. Lower temperatures result in little or no reaction, while higher temperatures will result in double nitration forming dinitrotoluenes.

Definition

ChEBI: 2-nitrotoluene is a mononitrotoluene that is toluene carrying a nitro substituent at position 2. It has a role as an environmental contaminant and a carcinogenic agent.

General Description

Light yellow oily liquid with a characteristic odor of aromatic nitro compounds. Sinks in water. Derived from toluene by nitration and separation by fractional distillation. Flash point 223°F.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Nitrotoluene is toxic by inhalation, ingestion and skin aborption, targeting the blood, central nervous system, skin, and gastrointestinal tract. Symptoms include, anoxia, weakness or dizziness, nausea and vomiting. If 2-Nitrotoluene contacts the eye, the eye should be irrigated immediately. If 2-Nitrotoluene contacts the skin, the area should be washed with soap. If inhaled, respiratory support should be administered. Finally, if ingested, medical attention should be sought. 2-Nitrotoluene also reacts with sulfuric acid, sodium hydroxide, hydrogen, sodium, tetranitromethane, reducing agents and strong oxidizers. 2-Nitrotoluene is very heat sensitive.

Hazard

Toxic by inhalation, ingestion, skin absorption. Methemoglobinemia. Probable carcinogen.

Health Hazard

INHALATION, INGESTION, OR SKIN: Headache, flushing of face, dizziness, dyspnea (difficult breathing), cyanosis, nausea, vomiting, muscular weakness, increased pulse and respiratory rate, irritability, and convulsions. SKIN: Irritation.

Safety Profile

Confirmed carcinogen. A poison. Moderately toxic by ingestion. Mucous membrane effects by inhalation. Mutation data reported. Combustible when exposed to heat or open flame. To fight fire, use water spray, fog, foam, CO2. Potentially explosive reaction with alkali (e.g., sodmm hydroxide). When heated to decomposition it emits toxic fumes of NOx. See also other methylnitrobenzene entries and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Carcinogenicity

o-Nitrotoluene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals and supporting data on mechanisms of carcinogenesis.

Environmental fate

Biological. Robertson et al. (1992) reported that toluene dioxygenases from Pseudomonas putida F1 and Pseudomonas sp. Strain JS 150 oxidized the methyl group forming 2-nitrobenzyl alcohol.

Purification Methods

Crystallise 2-nitrotoluene (repeatedly) from absolute EtOH by cooling in a Dry-ice/alcohol mixture. Further purify it by passing an alcoholic solution through a column of alumina. [Beilstein 5 IV 845.]

Check Digit Verification of cas no

The CAS Registry Mumber 88-72-2 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 2 respectively.
Calculate Digit Verification of CAS Registry Number 88-72:
(4*8)+(3*8)+(2*7)+(1*2)=72
72 % 10 = 2
So 88-72-2 is a valid CAS Registry Number.

88-72-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A13446)  2-Nitrotoluene, 99+%   

  • 88-72-2

  • 100g

  • 184.0CNY

  • Detail
  • Alfa Aesar

  • (A13446)  2-Nitrotoluene, 99+%   

  • 88-72-2

  • 500g

  • 323.0CNY

  • Detail
  • Alfa Aesar

  • (A13446)  2-Nitrotoluene, 99+%   

  • 88-72-2

  • 2500g

  • 694.0CNY

  • Detail
  • Sigma-Aldrich

  • (31567)  2-Nitrotoluene  analytical standard

  • 88-72-2

  • 31567-250MG

  • 312.39CNY

  • Detail
  • Aldrich

  • (438804)  2-Nitrotoluene  ≥99%

  • 88-72-2

  • 438804-5ML

  • 239.85CNY

  • Detail
  • Aldrich

  • (438804)  2-Nitrotoluene  ≥99%

  • 88-72-2

  • 438804-100ML

  • 377.91CNY

  • Detail

88-72-2SDS

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-nitrotoluene

1.2 Other means of identification

Product number -
Other names mononitrotoluene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. CBI
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:88-72-2 SDS

88-72-2Synthetic route

2-(2-nitrophenyl)acetic acid
3740-52-1

2-(2-nitrophenyl)acetic acid

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
copper(I) oxide In acetonitrile at 50℃;100%
With [Rh(OH)(cod)]2; 1,3-bis-(diphenylphosphino)propane; water; sodium hydroxide In tetrahydrofuran at 90℃; for 24h; Inert atmosphere;81%
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;75%
With copper diacetate; triethylamine at 35℃; for 21h; Sealed tube;26 %Spectr.
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / Inert atmosphere
1.2: 2 h / 110 °C / Inert atmosphere
2.1: sodium acetate / 22 h / 35 °C / Sealed tube
View Scheme
Benzoic acid (1R,6R)-5-methyl-6-nitro-cyclohex-3-enyl ester
118310-98-8, 118353-84-7

Benzoic acid (1R,6R)-5-methyl-6-nitro-cyclohex-3-enyl ester

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With potassium tert-butylate In benzene95%
2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

A

2,2'-dinitrobibenzyl
16968-19-7

2,2'-dinitrobibenzyl

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With tetraethylammonium perchlorate In acetonitrile controlled-potential electrolysis; further solvent - DMFA.;A 95%
B 2%
With diisopropyl phosphite; sodium hydride In tetrahydrofuran for 3h; Ambient temperature;A 86%
B 4%
With (C2H5)NClO4 In acetonitrile Mechanism; Rate constant; Product distribution; electrolysis;
With N-ethyl-N,N-diisopropylamine In dichloromethane for 5h; Inert atmosphere; Irradiation;A 73 %Spectr.
B 14 %Spectr.
2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction;90%
With bismuth (III) nitrate pentahydrate In toluene at 70 - 80℃; for 2h; Inert atmosphere;90%
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique;82%
4-methyl-3-nitrobenzoic acid
96-98-0

4-methyl-3-nitrobenzoic acid

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With sulfolane; sodium hydrogencarbonate at 200℃; for 2h;90%
toluene
108-88-3

toluene

A

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h;A 88%
B 12%
With sodium nitrite for 0.0166667h; Reagent/catalyst; Microwave irradiation;A 82%
B 15%
With bismuth(III) nitrate In tetrachloromethaneA 80%
B n/a
toluene
108-88-3

toluene

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

Conditions
ConditionsYield
With nitric acid In neat (no solvent) at 90℃; for 4h; regioselective reaction;A 9 %Chromat.
B 88%
With nitric acid In hexane at 90℃; for 4h; regioselective reaction;A 63.5 %Chromat.
B 36.4 %Chromat.
toluene
108-88-3

toluene

A

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With methanesulfonic acid; 1-butyl-3-methylimidazolium nitrate In water for 48h; Heating / reflux;A n/a
B n/a
C 85%
With nitric acid; 1-butyl-3-methylimidazolium nitrate In water for 48h; Heating / reflux;A n/a
B n/a
C 85%
With nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate In water for 48h; Heating / reflux;A n/a
B n/a
C 70%
With nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate In water for 48h; Heating / reflux;A n/a
B n/a
C 70%
C12H9N3O6S2

C12H9N3O6S2

tetramethylstannane
594-27-4

tetramethylstannane

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In tetrahydrofuran at 40℃; for 3h;85%
tetramethylstannane
594-27-4

tetramethylstannane

2-Nitrobenzenediazonium Bisulfate
49732-37-8

2-Nitrobenzenediazonium Bisulfate

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In water; acetonitrile at 20℃; for 2h;84%
With palladium diacetate In water; acetonitrile at 20℃; for 2h;72%
(S)-(o-nitrobenzyl)-6-thioguanine
103240-13-7

(S)-(o-nitrobenzyl)-6-thioguanine

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

(o-aminobenzyl)-6-thioguanine

(o-aminobenzyl)-6-thioguanine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethanol under 1551.4 Torr; for 24h; Product distribution; effect of presence of morpholine;A n/a
B 80%
toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With copper(II) nitrate on K10 montmorillonite; acetic anhydride In tetrachloromethane for 120h; Ambient temperature;A 1%
B 79%
C 20%
With nitric acid In trifluoroacetic acid at 25℃; Rate constant;A 0.7%
B 66.7%
C 32.6%
With ortho-methylphenyl iodide; potassium nitrate In trifluoroacetic acid for 0.5h; Product distribution; nitration of aromatic compounds in the presence of aryl iodides; other temperatures, other reagents;A n/a
B 64%
C 33%
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
190788-59-1

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

methyl iodide
74-88-4

methyl iodide

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With C21H30ClNPPd; potassium tert-butylate In tert-Amyl alcohol at 65℃; for 18h; Sealed tube; Inert atmosphere; Glovebox;78%
Diethyl 2-(2-nitrophenyl)propanedioate
10565-14-7

Diethyl 2-(2-nitrophenyl)propanedioate

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With magnesium chloride In N,N-dimethyl acetamide at 140 - 150℃; for 24h; Decarboxylation; Krapcho's reaction;77%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

A

2,2'-dinitrobibenzyl
16968-19-7

2,2'-dinitrobibenzyl

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

C

diisopropyl (2-nitrophenyl)methyl phosphonate

diisopropyl (2-nitrophenyl)methyl phosphonate

Conditions
ConditionsYield
With sodium hydride In isopropyl alcohol for 3h; Ambient temperature;A 74%
B 18%
C 6%
toluene
108-88-3

toluene

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 70℃; for 2h;70%
With nitramide; sulfuric acid In water at -15 - -2℃; for 2.25h;18%
With sulfuric acid; nitric acid at 20℃;
trimethyl(2-nitrobenzyl)silane
17876-76-5

trimethyl(2-nitrobenzyl)silane

benzaldehyde
100-52-7

benzaldehyde

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

α-phenyl-2-nitrophenethyl alcohol
16764-13-9

α-phenyl-2-nitrophenethyl alcohol

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;A n/a
B 70%
2-iodo-6-nitrotoluene
41252-98-6

2-iodo-6-nitrotoluene

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine; benzyl alcohol In 1,2-dimethoxyethane at 90℃; Inert atmosphere;70%
N-nitro-2,6-dimethylpyridinium tetrafluoroborate

N-nitro-2,6-dimethylpyridinium tetrafluoroborate

toluene
108-88-3

toluene

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
Product distribution; Ambient temperature;A 3%
B 32%
C 65%
trimethyl(2-nitrobenzyl)silane
17876-76-5

trimethyl(2-nitrobenzyl)silane

benzyl bromide
100-39-0

benzyl bromide

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

1-nitro-2-phenethylbenzene
6796-01-6

1-nitro-2-phenethylbenzene

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given;A n/a
B 60%
dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 3h; Heating;60%
2-iodo-6-nitrotoluene
41252-98-6

2-iodo-6-nitrotoluene

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

2,2'-dimethyl-3,3'-dinitrobiphenyl
31354-19-5

2,2'-dimethyl-3,3'-dinitrobiphenyl

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide at 190℃; for 24h;A n/a
B 53%
toluene
108-88-3

toluene

A

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

C

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 20℃; for 0.00416667h;A 37.8%
B 52.2%
C 4.3%
With di-tert-butyl dicarbonate; nitric acid at 4℃; for 50h; Product distribution / selectivity;A 47%
B 45%
C 5.5%
With butanoic acid anhydride; nitric acid at 50℃; for 4h;
1-o-Nitrobenzyl-4-methylpyridinium bromide

1-o-Nitrobenzyl-4-methylpyridinium bromide

A

picoline
108-89-4

picoline

B

2,2'-dinitrobibenzyl
16968-19-7

2,2'-dinitrobibenzyl

C

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 0.89 V;A 52%
B n/a
C 18%
1-o-Nitrobenzyl-4-methylpyridinium bromide

1-o-Nitrobenzyl-4-methylpyridinium bromide

A

picoline
108-89-4

picoline

B

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With tetraethylammonium perchlorate In acetonitrile at 20℃; Rate constant; electrolyse, -0.89 V;A 52%
B 18%
2-bromo-6-nitrotoluene
55289-35-5

2-bromo-6-nitrotoluene

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

Conditions
ConditionsYield
With 0.60mol% Pd/C; hydrogen; sodium hydrogencarbonate In methanol at 20℃; for 0.583333h; regioselective reaction;52%
2-(2-nitrophenyl)acetic acid
3740-52-1

2-(2-nitrophenyl)acetic acid

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;A 52%
B 46%
potassium 2-(2-nitrophenyl)acetate
1316859-98-9

potassium 2-(2-nitrophenyl)acetate

(S)-5-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-ethylcyclopent-1-en-1-yltrifluoromethanesulfonate

(S)-5-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-ethylcyclopent-1-en-1-yltrifluoromethanesulfonate

A

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

B

(S)-tert-butyl(3-(1-ethyl-2-(2-nitrobenzyl)cyclopent-2-en-1-yl)propoxy)dimethylsilane

(S)-tert-butyl(3-(1-ethyl-2-(2-nitrobenzyl)cyclopent-2-en-1-yl)propoxy)dimethylsilane

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); XPhos In diethylene glycol dimethyl ether at 140℃; for 2h; Inert atmosphere;A n/a
B 52%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-nitrophenylmethyl bromide
3958-60-9

2-nitrophenylmethyl bromide

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux;100%
Stage #1: 1-methyl-2-nitrobenzene With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane for 0.333333h;
Stage #2: With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane at 72 - 75℃; for 2h; Solvent; Temperature;
98.5%
With sodium hypochlorite; 2,2'-azobis(isobutyronitrile); hydrogen bromide In chlorobenzene at 85℃; for 7h; Temperature; Solvent;97%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

o-toluidine
95-53-4

o-toluidine

Conditions
ConditionsYield
With hydrogen; palladium In methanol at 25℃; under 2327.2 Torr; for 1.5h;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;100%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N,N'-Di-o-tolyl-diazene N-oxide
956-31-0, 51284-68-5, 116723-89-8

N,N'-Di-o-tolyl-diazene N-oxide

Conditions
ConditionsYield
With bismuth for 1.5h;100%
With sodium tetrahydroborate; water In ethanol at 30℃; for 6h; chemoselective reaction;92%
With oxygen; ammonium chloride; zinc In [bmim][BF4]; water at 20℃; for 18h;88%
propyl cyanide
109-74-0

propyl cyanide

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N-butyl-2-methylaniline
7277-86-3

N-butyl-2-methylaniline

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; for 4.5h;
Stage #2: propyl cyanide In methanol; water
100%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

propiononitrile
107-12-0

propiononitrile

2-methyl-N-propylaniline
83627-55-8

2-methyl-N-propylaniline

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;
Stage #2: propiononitrile In methanol; water
100%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

2-(2-nitrophenyl)acetic acid
3740-52-1

2-(2-nitrophenyl)acetic acid

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene; oxalic acid diethyl ester With sodium In ethanol at 20 - 45℃; for 3h;
Stage #2: With water In ethanol at 60℃; for 1h; Reagent/catalyst;
99.8%
Stage #1: 1-methyl-2-nitrobenzene; oxalic acid diethyl ester With sodium In ethanol at 45℃; for 3h;
Stage #2: With water In ethanol at 60℃; for 1h;
99.8%
formaldehyd
50-00-0

formaldehyd

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

Conditions
ConditionsYield
With sodium hydroxide In water; dimethyl sulfoxide at 50℃; for 1h; Large scale reaction;99.5%
64%
With potassium hydroxide In water; dimethyl sulfoxide at 0℃; for 5h;46%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

nitrobenzotrichloride
10542-55-9

nitrobenzotrichloride

Conditions
ConditionsYield
With chlorine at 120℃; for 6h; Temperature;99.2%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N-(o-tolyl)hydroxylamine
611-22-3

N-(o-tolyl)hydroxylamine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water; 1,2-dichloro-ethane at 45℃; for 2h; Catalytic behavior; Temperature;99%
With hydrazine hydrate In ethanol; dichloromethane at 0 - 2℃; for 6h; Solvent; Temperature;91.8%
With sodium tetrahydroborate; palladium diacetate In ethanol; dichloromethane; water at 20℃; for 0.133333h;84%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

o-toluidine hydrochloride
636-21-5

o-toluidine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With hydrogen In ethanol at 25℃; under 11172.7 Torr; Flow reactor;
Stage #2: With hydrogenchloride In ethanol Flow reactor; chemoselective reaction;
99%
With hydrogenchloride; tin(ll) chloride In ethanol; water at 30℃; Rate constant; Mechanism; various concentration of HCl; different amounts of H2O as solvent;
Stage #1: 1-methyl-2-nitrobenzene With phosgene; sodium tetrahydroborate; copper(II) sulfate In methanol at 20℃;
Stage #2: With hydrogenchloride In methanol; diethyl ether
545 mg
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)-2-methylaniline
34160-14-0

N-(4-methylphenyl)-2-methylaniline

Conditions
ConditionsYield
With bis(acetylacetonato)palladium(II); potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;99%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

4-methyl-3-nitrobenzenesulfonic acid,sodium salt

4-methyl-3-nitrobenzenesulfonic acid,sodium salt

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With chlorosulfonic acid at 115℃; for 4h;
Stage #2: With sodium carbonate In water at 20℃;
98.6%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

trans-β-dimethylamino-2-nitrostyrene
32991-03-0

trans-β-dimethylamino-2-nitrostyrene

Conditions
ConditionsYield
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 2h; microwave irradiation;98%
In N,N-dimethyl-formamide at 140℃; for 24h;88%
In N,N-dimethyl-formamide for 26h; Heating;86%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

Conditions
ConditionsYield
With nitric acid; acetic anhydride at 50℃; for 4h;97%
bei der Nitrierung;
With Nitroethane; boron trifluoride-dinitrogen tetraoxide
2-Chloro-F-propane
76-18-6

2-Chloro-F-propane

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

heptafluoroisopropyl-3-methyl-4-nitrobenzene
238098-38-9

heptafluoroisopropyl-3-methyl-4-nitrobenzene

Conditions
ConditionsYield
With hydrogen fluoride; antimony pentafluoride at 80℃; for 2h; Friedel-Crafts Alkylation; Autoclave; Industrial scale;97%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

benzaldehyde
100-52-7

benzaldehyde

N-benzyl-2-methylaniline
5405-13-0

N-benzyl-2-methylaniline

Conditions
ConditionsYield
With hydrogen In toluene at 80℃; under 15001.5 Torr; for 18h; Autoclave;96%
With formic acid; Au/TiO2-R In water at 80℃; under 760.051 Torr; for 9h; Inert atmosphere; Green chemistry; chemoselective reaction;91%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h;88%
formic acid
64-18-6

formic acid

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2'-methylformanilide
94-69-9

2'-methylformanilide

Conditions
ConditionsYield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 3.5h; Inert atmosphere; chemoselective reaction;96%
With palladium(II) trifluoroacetate; triphenylphosphine In water at 80℃; for 0.333333h; Sealed tube; Green chemistry;80%
With palladium particles distributed over the surface of fibrous silica nanospheres modified via aminopropyltriethoxysilane In toluene at 70℃; for 3h;96 %Chromat.
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-aminobenzaldehyde
529-23-7

2-aminobenzaldehyde

Conditions
ConditionsYield
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In methanol at 60℃; for 3h; Temperature; Solvent;95.9%
methanol
67-56-1

methanol

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

phenol
108-95-2

phenol

4-phenylamino-3-methyl-1-methoxybenzene
41317-15-1

4-phenylamino-3-methyl-1-methoxybenzene

Conditions
ConditionsYield
Stage #1: methanol; 1-methyl-2-nitrobenzene With 3 % platinum on carbon; hydrogen In water at 50℃; under 750.075 Torr; for 8h; Autoclave; Inert atmosphere;
Stage #2: phenol With 3 % platinum on carbon In cyclohexanone at 250℃; under 7500.75 Torr; for 2h; Autoclave; Inert atmosphere;
95.4%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2,2'-dinitrobibenzyl
16968-19-7

2,2'-dinitrobibenzyl

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere;
Stage #2: With bromine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
95%
With 5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;88%
With sodium; formic acid ethyl ester In hexane at 0 - 5℃; for 24h;70.4%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

Conditions
ConditionsYield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9;95%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium bromide at 40℃; for 12h; Temperature;94.2%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N,N-dimethyl-2-(2-nitrophenyl)ethenylamine
20973-67-5

N,N-dimethyl-2-(2-nitrophenyl)ethenylamine

Conditions
ConditionsYield
In chloroform; N,N-dimethyl-formamide at 175℃; under 11251.1 Torr; for 2h; Solvent; Temperature; Pressure;95%
In N,N-dimethyl-formamide at 175℃; under 3750.38 Torr; for 2h;91%
In N,N-dimethyl-formamide for 26h; Heating;86%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

acetic anhydride
108-24-7

acetic anhydride

N-(2-methylphenyl)acetamide
120-66-1

N-(2-methylphenyl)acetamide

Conditions
ConditionsYield
Stage #1: 1-methyl-2-nitrobenzene With sodium tetrahydroborate In water at 60 - 70℃; Green chemistry;
Stage #2: acetic anhydride In water at 60 - 70℃; Green chemistry;
95%
Stage #1: 1-methyl-2-nitrobenzene In water for 0.0833333h;
Stage #2: With sodium tetrahydroborate In water at 65℃; for 0.05h;
Stage #3: acetic anhydride In water at 65℃; for 0.0333333h; Catalytic behavior;
95%
With sodium tetrahydroborate at 60℃; for 0.15h;93%
With samarium; acetic acid In methanol at 20℃; for 1.5h;88%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

A

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

B

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

Conditions
ConditionsYield
With nitric acid; Chloroacetic anhydride at 50℃; for 4h;A 94%
B 5%
With dinitrogen pentoxide; H-faujasite zeolite F-712 In dichloromethaneA 77%
B 15%
With nitric acid at 50℃; for 3h;A 71.5%
B 28.5%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

Conditions
ConditionsYield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;94%
Stage #1: 1-methyl-2-nitrobenzene With bromine In propan-1-ol at 20℃; for 0.25h; UV-irradiation;
Stage #2: With sodium hydrogencarbonate In propan-1-ol for 2h; Solvent; Reflux; UV-irradiation;
89%
With oxygen In acetonitrile at 20℃; for 12h; Irradiation;80%

88-72-2Relevant articles and documents

Aromatic nitration with nitric acid/trifluoromethanesulfonic anhydride

Olah,Reddy,Prakash

, p. 1087 - 1089 (1992)

Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/

Nitrobenzyl Derivatives as Bioreductive Alkylating Agents: Evidence for the Reductive Formation of a Reactive Intermediate

Kirkpatrick, D. L.,Johnson, K. E.,Sartorelli, A. C.

, p. 2048 - 2052 (1986)

o- and p-nitrobenzyl chlorides and carbamates were chemically and electrochemically reduced in the presence and absence of the nucleophile morpholine; activation of these compounds by reduction was required to produce an intermediate capable of alkylation.The reduction products formed by the catalytic hydrogenation of each compound were examined by gas chromatography-mass spectrometry.In addition, the products generated by controlled-potential electrolysis were examined by ESR and NMR spectrometry.After a one-electron reduction, o- and p-nitrobenzyl chlorides were activated to the nitrobenzyl radicals, which subsequently dimerized to the dinitrobibenzyl derivatives or reacted with morpholine when present in the reaction medium to form the (nitrobenzyl)morpholine adducts.The nitrobenzyl carbamates were not activated after a one-electron reduction; however, the morpholine and the ether adducts of these agents were observed after catalytic hydrogenation.It was assumed that an intermediate or intermediates formed after the one-electron reduction product, or the full reduction product of the carbamates, were capable of alkylating various nucleophiles.Chemical reduction of the potential bioreductive alkylating agent (o-nitrobenzyl)-6-thioguanine produced (o-aminobenzyl)-6-thioguanine, indicating a lack of formation of a reactive electrophile by reduction. (o-, (m-, and (p-nitrobenzyl)-6-thioguanine analogues were also examined for cytotoxic activity toward EMT6 tumor cells under aerobic and hypoxic conditions.In agreement with the inability of (o-nitrobenzyl)-6-thioguanine to form a reactive species after chemical reduction, no decrease in the survival of neoplastic cells exposed to 10-4 M drug occurred under either aerobic or hypoxic conditions.

Application of H-ZSM-5 Zeolite for Regioselective Mononitration of Toluene

Kwok, Thomas J.,Jayasuriya, Keerthi,Damavarapu, Reddy,Brodman, Bruce W.

, p. 4939 - 4942 (1994)

The nitration of toluene with n-propyl nitrate has been carried out in the presence of H-ZSM-5 as the catalyst.Several H-ZSM-5 catalysts with different Si/Al ratios were investigated to determine the influence of varying Si/Al ratios on the catalytic activity.It was found that high Si/Al ratios enhanced the regioselectivity for the p-nitrotoluene over the ortho isomer under comparable conditions.The best o:m:p product distribution (5:0:95) was achieved using H-ZSM-5 with a Si/Al ratio of 1000.The isolable yield is 54percent.In contrast to conventional nitration methods, the product distribution reported in this study is remarkable.

Some Aspects of Nitration of Aromatics by Lower Oxidation States of Nitrogen

Milligan, Barton

, p. 1495 - 1500 (1983)

Nitration of benzene and toluene in trifluoroacetic acid (TFA) solution with sodium nitrite (N(III)) and nitrogen dioxide (N(IV)) occurs relatively slowly to produce mononitroarenes and oxidized byproducts.The yield of nitroarene improves as the ratio of

Aromatic Substitution. 50. Mercury(II)-Promoted Azeotropic Nitration of Aromatics over Nafion-H Solid Superacidic Catalyst

Olah, George A.,Krishnamurthy, V. V.,Narang, Subhash C.

, p. 596 - 598 (1982)

-

Regioselective catalyzed nitration of toluene by zeolites

Dong, Xiongzi,Peng, Xinhua

, p. 2341 - 2342 (2015)

The nitration of toluene with nitric acid and nitrogen dioxide as nitration agent was studied. The effect of zeolite catalysts was also discussed. By using zeolite as catalysis, the yield of nitro-toluene was improved with nitric acid as nitration agent. The conversion of toluene and yield of nitro-toluene were both greatly enhanced with nitrogen dioxide as nitration agent.

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.

, p. 25841 - 25847 (2021/08/09)

Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.

Selective Mild Oxidation of Anilines into Nitroarenes by Catalytic Activation of Mesoporous Frameworks Linked with Gold-Loaded Mn3O4 Nanoparticles

Armatas, Gerasimos S.,Daikopoulou, Vassiliki,Koutsouroubi, Eirini D.,Lykakis, Ioannis N.,Skliri, Euaggelia

, (2021/11/01)

This work reports the synthesis and catalytic application of mesoporous Au-loaded Mn3O4 nanoparticle assemblies (MNAs) with different Au contents, i. e., 0.2, 0.5 and 1 wt %, towards the selective oxidation of anilines into the corresponding nitroarenes. Among common oxidants, as well as several supported gold nanoparticle platforms, Au/Mn3O4 MNAs containing 0.5 wt % Au with an average particle size of 3–4 nm show the best catalytic performance in the presence of tert-butyl hydroperoxide (TBHP) as a mild oxidant. In all cases, the corresponding nitroarenes were isolated in high to excellent yields (85–97 %) and selectivity (>98 %) from acetonitrile or greener solvents, such as ethyl acetate, after simple flash chromatography purification. The 0.5 % Au/Mn3O4 catalyst can be isolated and reused four times without a significant loss of its activity and can be applied successfully to a lab-scale reaction of p-toluidine (1 mmol) leading to the p-nitrotulene in 83 % yield. The presence of AuNPs on the Mn3O4 surface enhances the catalytic activity for the formation of the desired nitroarene. A reasonable mechanism was proposed including the plausible formation of two intermediates, the corresponding N-aryl hydroxylamine and the nitrosoarene.

NITRATION

-

Page/Page column 36; 41; 46; 64; 37; 47; 42; 65, (2020/05/28)

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.

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