88-72-2

Basic information

• Product Name: 2-Nitrotoluene
• Synonyms: O-NITROTOLUENE;o-nitrophenylmethane;1-methyl-2-nitro-benzen;Benzene,1-methyl-2-nitro-;nsc9577;o-Methylnitrobenzene;o-nitro-toluen;o-nitrotoluol
• CAS NO: 88-72-2
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14
• EINECS: 201-853-3
• Product Categories: Intermediates of Dyes and Pigments;2-MethyInitrobenzene;Organics;8000 Series Solidwaste Methods;Analytical Standards;AromaticsEnvironmental Standards;Chemical Class;Environmental Standards;ExplosivesEPA;Method 8330Alphabetic;N;NA - NIAnalytical Standards;Nitro CompoundsChromatography;Solid WasteMore...Close...;Volatiles/ Semivolatiles
• Mol File: 88-72-2.mol
• Article Data: 248

Chemical Properties

• Melting Point: -9 °C
• Boiling Point: 225 °C(lit.)
• Flash Point: 223 °F
• Appearance: Clear yellow to yellow-green/Liquid
• Density: 1.163 g/mL at 25 °C(lit.)
• Vapor Density: 4.72
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• Storage Temp.: 2-8°C
• Solubility: 0.65g/l (experimental)
• Explosive Limit: 1.47-8.8%(V)
• Water Solubility: 0.44 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with oxidizing agents, strong bases, sulfuric acid, reducing agents, hydrogen, sodium.
• Merck: 14,6650
• BRN: 1907580
• CAS DataBase Reference: 2-Nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrotoluene(88-72-2)
• EPA Substance Registry System: 2-Nitrotoluene(88-72-2)

Safety Data

• Hazard Codes: T,N,F
• Statements: 45-46-22-51/53-62-36/37/38-23/24/25-11-36-20/21/22
• Safety Statements: 53-45-61-27-16-36/37-26
• RIDADR: UN 1664 6.1/PG 2
• WGK Germany: 3
• RTECS: XT3150000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 88-72-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Nitrotoluene is used as an intermediate in the synthesis of azo dyes, sulfur dyes, rubber chemicals, and agricultural chemicals. It helps in producing typical intermediates such as 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).
Used in Dye Industry:
In the dyestuff industry, 2-Nitrotoluene is used as an intermediate for the synthesis of o-toluidine, which is essential for the production of various dyes.
Used in Analytical Chemistry:
2-Nitrotoluene is employed as a reagent in detecting and photometrically determining oxidizing agents. It is also utilized in the determination of prussic acid content in the air.
Used in Pharmaceutical and Agricultural Chemicals:
2-Nitrotoluene acts as a precursor to prepare compounds such as 2-amino-4-chlorotoluene, 2-amino-6-chlorotoluene, nitrotoluenesulfonic acids, and toluene nitrosulfonic chlorides, which find applications in pharmaceutical and agricultural chemical industries.
Used in Microbial Culture Media:
2-Nitrotoluene serves as a nitrogen supplement in the culture medium of Pseudomonas sp. strain ClS1 and as a carbon and energy supplement in the culture medium of Pseudomonas sp. strain JS42.

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

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.

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.]

Synthetic route

2-(2-nitrophenyl)acetic acid (3740-52-1) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With potassium tert-butylate In benzene	95%

2-nitrophenylmethyl bromide (3958-60-9) → 2,2'-dinitrobibenzyl (16968-19-7) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With sulfolane; sodium hydrogencarbonate at 200℃; for 2h;	90%

toluene (108-88-3) → 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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 tetrachloromethane	A 80% B n/a

toluene (108-88-3) → 1-methyl-2-nitrobenzene (88-72-2) + 2,4-dinitrotoluene (121-14-2)

Conditions	Yield
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) → 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2) + benzoic acid (65-85-0)

Conditions	Yield
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 + tetramethylstannane (594-27-4) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
palladium diacetate In tetrahydrofuran at 40℃; for 3h;	85%

tetramethylstannane (594-27-4) + 2-Nitrobenzenediazonium Bisulfate (49732-37-8) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2) + (o-aminobenzyl)-6-thioguanine

Conditions	Yield
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) → 1-methyl-3-nitrobenzene (99-08-1) + 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) + methyl iodide (74-88-4) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With magnesium chloride In N,N-dimethyl acetamide at 140 - 150℃; for 24h; Decarboxylation; Krapcho's reaction;	77%

diisopropyl hydrogenphosphonate (1809-20-7) + 2-nitrophenylmethyl bromide (3958-60-9) → 2,2'-dinitrobibenzyl (16968-19-7) + 1-methyl-2-nitrobenzene (88-72-2) + diisopropyl (2-nitrophenyl)methyl phosphonate

Conditions	Yield
With sodium hydride In isopropyl alcohol for 3h; Ambient temperature;	A 74% B 18% C 6%

toluene (108-88-3) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) + benzaldehyde (100-52-7) → 1-methyl-2-nitrobenzene (88-72-2) + α-phenyl-2-nitrophenethyl alcohol (16764-13-9)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine; benzyl alcohol In 1,2-dimethoxyethane at 90℃; Inert atmosphere;	70%

N-nitro-2,6-dimethylpyridinium tetrafluoroborate + toluene (108-88-3) → 1-methyl-3-nitrobenzene (99-08-1) + 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
Product distribution; Ambient temperature;	A 3% B 32% C 65%

trimethyl(2-nitrobenzyl)silane (17876-76-5) + benzyl bromide (100-39-0) → 1-methyl-2-nitrobenzene (88-72-2) + 1-nitro-2-phenethylbenzene (6796-01-6)

Conditions	Yield
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) + 2-Chloronitrobenzene (88-73-3) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 3h; Heating;	60%

2-iodo-6-nitrotoluene (41252-98-6) → 1-methyl-2-nitrobenzene (88-72-2) + 2,2'-dimethyl-3,3'-dinitrobiphenyl (31354-19-5)

Conditions	Yield
With copper In N,N-dimethyl-formamide at 190℃; for 24h;	A n/a B 53%

toluene (108-88-3) → 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2) + 2,4-dinitrotoluene (121-14-2)

Conditions	Yield
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 → picoline (108-89-4) + 2,2'-dinitrobibenzyl (16968-19-7) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 0.89 V;	A 52% B n/a C 18%

1-o-Nitrobenzyl-4-methylpyridinium bromide → picoline (108-89-4) + 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
With tetraethylammonium perchlorate In acetonitrile at 20℃; Rate constant; electrolyse, -0.89 V;	A 52% B 18%

2-bromo-6-nitrotoluene (55289-35-5) → 1-methyl-2-nitrobenzene (88-72-2)

Conditions	Yield
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) → 1-methyl-2-nitrobenzene (88-72-2) + 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
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) + (S)-5-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-ethylcyclopent-1-en-1-yltrifluoromethanesulfonate → 1-methyl-2-nitrobenzene (88-72-2) + (S)-tert-butyl(3-(1-ethyl-2-(2-nitrobenzyl)cyclopent-2-en-1-yl)propoxy)dimethylsilane

Conditions	Yield
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) → 2-nitrophenylmethyl bromide (3958-60-9)

Conditions	Yield
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) → o-toluidine (95-53-4)

Conditions	Yield
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) → N,N'-Di-o-tolyl-diazene N-oxide (956-31-0, 51284-68-5, 116723-89-8)

Conditions	Yield
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) + 1-methyl-2-nitrobenzene (88-72-2) → N-butyl-2-methylaniline (7277-86-3)

Conditions	Yield
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) + propiononitrile (107-12-0) → 2-methyl-N-propylaniline (83627-55-8)

Conditions	Yield
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) + oxalic acid diethyl ester (95-92-1) → 2-(2-nitrophenyl)acetic acid (3740-52-1)

Conditions	Yield
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) + 1-methyl-2-nitrobenzene (88-72-2) → 2-nitro-benzeneethanol (15121-84-3)

Conditions	Yield
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) → nitrobenzotrichloride (10542-55-9)

Conditions	Yield
With chlorine at 120℃; for 6h; Temperature;	99.2%

1-methyl-2-nitrobenzene (88-72-2) → N-(o-tolyl)hydroxylamine (611-22-3)

Conditions	Yield
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) → o-toluidine hydrochloride (636-21-5)

Conditions	Yield
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) + p-toluidine (106-49-0) → N-(4-methylphenyl)-2-methylaniline (34160-14-0)

Conditions	Yield
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) → 4-methyl-3-nitrobenzenesulfonic acid,sodium salt

Conditions	Yield
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) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → trans-β-dimethylamino-2-nitrostyrene (32991-03-0)

Conditions	Yield
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) → 2,4-dinitrotoluene (121-14-2)

Conditions	Yield
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) + 1-methyl-2-nitrobenzene (88-72-2) → heptafluoroisopropyl-3-methyl-4-nitrobenzene (238098-38-9)

Conditions	Yield
With hydrogen fluoride; antimony pentafluoride at 80℃; for 2h; Friedel-Crafts Alkylation; Autoclave; Industrial scale;	97%

1-methyl-2-nitrobenzene (88-72-2) + benzaldehyde (100-52-7) → N-benzyl-2-methylaniline (5405-13-0)

Conditions	Yield
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) + 1-methyl-2-nitrobenzene (88-72-2) → 2'-methylformanilide (94-69-9)

Conditions	Yield
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) → 2-aminobenzaldehyde (529-23-7)

Conditions	Yield
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) + 1-methyl-2-nitrobenzene (88-72-2) + phenol (108-95-2) → 4-phenylamino-3-methyl-1-methoxybenzene (41317-15-1)

Conditions	Yield
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) → 2,2'-dinitrobibenzyl (16968-19-7)

Conditions	Yield
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) → ortho-nitrobenzoic acid (552-16-9)

Conditions	Yield
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) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-2-(2-nitrophenyl)ethenylamine (20973-67-5)

Conditions	Yield
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) + acetic anhydride (108-24-7) → N-(2-methylphenyl)acetamide (120-66-1)

Conditions	Yield
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) → 2,4-dinitrotoluene (121-14-2) + 2,6-dinitrotoluene (606-20-2)

Conditions	Yield
With nitric acid; Chloroacetic anhydride at 50℃; for 4h;	A 94% B 5%
With dinitrogen pentoxide; H-faujasite zeolite F-712 In dichloromethane	A 77% B 15%
With nitric acid at 50℃; for 3h;	A 71.5% B 28.5%

1-methyl-2-nitrobenzene (88-72-2) → 2-nitro-benzaldehyde (552-89-6)

Conditions	Yield
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%

Upstream product

• 110-89-4 piperidine 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 56-23-5 tetrachloromethane 
• 100-52-7 benzaldehyde 
• 121-14-2 2,4-dinitrotoluene 
• 611-05-2 4-nitro-3-methylaniline 
• 2229-07-4 methyl radical 
• 98-95-3 nitrobenzene 
• 625-58-1 ethyl nitrate 
• 108-88-3 toluene 
• 928-45-0 butyl nitrate 
• 21823-34-7 1-chloro-2-nitrooxy-ethane 
• 591-09-3 nitro acetate 
• 76-06-2 chloropicrin 

Downstream Products

• 21259-33-6 N-(2-methylphenyl)pyridine-2-thiocarboxamide 
• 584-90-7 2,2'-dimethylazobenzene 
• 611-21-2 N,2-dimethylaniline 
• 76947-17-6 4,4'-dimethyl-3,3'-dinitrodiphenylmethane 
• 2283-00-3 4-methoxy-6-methyl-5-(2-nitro-benzyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 6345-63-7 1-diacetoxymethyl-2-nitro-benzene 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 33331-19-0 N-(2-nitrobenzyl)aniline 
• 35427-94-2 N-(2-tolyl)-C-phenylnitrone 
• 21911-61-5 N-(2-methylphenyl)glycine 
• 1016-59-7 1-methyl-phenazine 
• 29418-37-9 (2'-methyl)-2-hydroxyazobenzene 
• 123-30-8 4-amino-phenol 
• 34810-71-4 N-[(2-methylphenyl)imino]benzenimine oxide 

Relevant articles and documents

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