619-15-8

Basic information

• Product Name: 2,5-DINITROTOLUENE
• Synonyms: 2,5-dinitro-toluen;2,5-Dinitrotoluene;2,5-DNT;2-Methyl-1,4-dinitrobenzene;Toluene, 2,5-dinitro-;1-METHYL-2,5-DINITROBENZENE;2,5-Dinitrotoluol;1,4-Dinitro-2-methylbenzene
• CAS NO: 619-15-8
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13354
• EINECS: 210-581-4
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 619-15-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 50.33°C
• Boiling Point: 320.51°C (rough estimate)
• Flash Point: 157.1 °C
• Appearance: /
• Density: 1.2820
• Vapor Pressure: 0.000907mmHg at 25°C
• Refractive Index: 1.4420 (estimate)
• CAS DataBase Reference: 2,5-DINITROTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DINITROTOLUENE(619-15-8)
• EPA Substance Registry System: 2,5-DINITROTOLUENE(619-15-8)

Safety Data

• Hazard Codes: T,N
• Statements: 45-23/24/25-48/22-62-68-51/53
• Safety Statements: 53-45-61
• RIDADR: 3454
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 619-15-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H6N2O4/c1-5-4-6(8(10)11)2-3-7(5)9(12)13/h2-4H,1H3

Synthetic route

2-methyl-4-nitro-benzenamine (99-52-5) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With tert.-butylhydroperoxide; 3 A molecular sieve; zirconium(IV) tert-butoxide In dichloromethane for 2.5h; Ambient temperature;	87%
beim Ersatz der Aminogruppe durch die Nitrogruppe;
nach Sandmeyer;

1-methyl-3-nitrobenzene (99-08-1) → 1-methyl-2,3-dinitrobenzene (602-01-7) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With nitronium hexafluorophosphate; sulfuric acid	A 28.4% B 60.1% C 9.9%
With nitronium hexafluorophosphate In nitromethane at 24.84℃;

1-methyl-3-nitrobenzene (99-08-1) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
bei der Nitrierung;
Nitrierung;

4-nitro-3-methylaniline (611-05-2) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;
Multi-step reaction with 2 steps 1: Caro's acid 2: fuming nitric acid View Scheme

toluquinone dioxime (36164-91-7) → 2,5-dinitrotoluene (619-15-8)

2-nitroso-5-nitrotoluene (57610-10-3) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With nitric acid

2,5-dinitro-4-methylaniline (70343-10-1) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With ethanol; sulfuric acid Diazotization.Erhitzen des Reaktionsgemisches mit Salpetersaeure;

2-methyl-3,6-dinitro-aniline (56207-39-7) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With ethanol; sulfuric acid; sodium nitrite

2-methyl-1,4-dinitrosobenzene (16832-42-1) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With nitric acid

2-nitro-5-nitrosotoluene (408328-19-8) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With nitric acid

4-methyl-2,5-dinitro-benzoic acid (101084-63-3) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With hydrogenchloride at 250℃;

4-nitroso-2-methylaniline (74231-59-7) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With caro's acid Oxydation mit rauchender Salpetersaeure;

para-dinitrobenzene (100-25-4) + methylmagnesium chloride (676-58-4) → 2,5-dinitrotoluene (619-15-8) + trans-5,6-dimethyl-1,4-dinitrocyclohexa-1,3-diene (122834-00-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) THF, -70 deg C, 10 min, 2.) THF, -10 deg C, 60 min; Yield given. Multistep reaction. Yields of byproduct given;

2-methyl-4-nitrobenzenediazonium tetrafluoroborate → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With sodium nitrite In water at 39.7 - 58.4℃; Kinetics;

C7H6N3O2(1+)*BF4(1-) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With sodium nitrite In water at 25 - 47.4℃; Kinetics;

nitric acid (7697-37-2) + 2-methyl-4-nitro-benzenamine (99-52-5) + Caro's acid → 2,5-dinitrotoluene (619-15-8)

1-methyl-3-nitrobenzene (99-08-1) + nitric acid (7697-37-2) → 1-methyl-2,3-dinitrobenzene (602-01-7) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

1-methyl-3-nitrobenzene (99-08-1) + sulfuric acid (7664-93-9) + water (7732-18-5) + nitric acid (7697-37-2) → 1-methyl-2,3-dinitrobenzene (602-01-7) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
at 40 - 70℃; Product distribution;

1-methyl-3-nitrobenzene (99-08-1) + HNO3+H2SO4 → 1-methyl-2,3-dinitrobenzene (602-01-7) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

1-methyl-3-nitrobenzene (99-08-1) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 3,5-dinitrotoluene (618-85-9) + 1-methyl-2,3-dinitrobenzene (602-01-7) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
at 60 - 85℃;

1-methyl-3-nitrobenzene (99-08-1) → 2,5-dinitrotoluene (619-15-8) + 3.4-dinitro-toluene, 2.3-dinitro-toluene

Conditions	Yield
Nitrierung;

toluquinone dioxime (36164-91-7) + nitric acid (7697-37-2) → 2,5-dinitrotoluene (619-15-8)

diethyl ether (60-29-7) + toluquinone dioxime (36164-91-7) + dinitrogen tetraoxide (10544-72-6) → 2,5-dinitrotoluene (619-15-8)

hydrogenchloride (7647-01-0) + 4-methyl-2,5-dinitro-benzoic acid (101084-63-3) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
at 250℃; im Druckrohr;

2-nitro-5-nitrosotoluene (408328-19-8) + nitric acid (7697-37-2) → 2,5-dinitrotoluene (619-15-8)

2,3,6-trinitrotoluene (18292-97-2) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; ammonia / 110 - 120 °C 2: fuming sulfuric acid; absolute alcohol; sodium nitrite View Scheme

3-methyl-1,4-benzoquinone 4-oxime (13362-34-0) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydroxylamine / 60 - 70 °C 2: fuming nitric acid View Scheme

2-methyl-1,4-benzoquinone 4-oxime (13362-33-9) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydroxylamine / 60 - 70 °C 2: fuming nitric acid View Scheme

2,6-dinitrotoluene (606-20-2) → 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: ammonium sulfide; alcohol / auf dem Wasserbad 2: sulfuric acid 3: HNO3+H2SO4 / Erhitzen des Reaktionsprodukts mit konz.Schwefelsaeure 4: Caro's acid; concentrated sulfuric acid / Behandlung der Reaktionsprodukte mit Salpetersaeure 5: alcohol; ammonia / 110 - 120 °C 6: fuming sulfuric acid; absolute alcohol; sodium nitrite View Scheme
Multi-step reaction with 4 steps 1: ammonium sulfide; alcohol / auf dem Wasserbad 2: sulfuric acid 3: HNO3+H2SO4 / Erhitzen des Reaktionsprodukts mit konz.Schwefelsaeure 4: fuming sulfuric acid; absolute alcohol; sodium nitrite View Scheme

2,5-dinitrotoluene (619-15-8) + ethanethiol (75-08-1) → 1-(ethylsulfanyl)-2-methyl-4-nitrobenzene (83759-95-9)

Conditions	Yield
With lithium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃;	97%

2,5-dinitrotoluene (619-15-8) → 2-methyl-p-phenylenediamine (95-70-5)

Conditions	Yield
With sodium tetrahydroborate In water at 20℃; for 0.583333h; Inert atmosphere;	95%
With hydrogenchloride; tin

triethyl borane (97-94-9) + 2,5-dinitrotoluene (619-15-8) → 1-ethyl-2-methyl-4-nitro-benzene

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h;	76%

2,5-dinitrotoluene (619-15-8) + sodium methylate (124-41-4) → 5-methoxy-2-nitrotoluene (5367-32-8)

2,5-dinitrotoluene (619-15-8) → 2,5-dinitrobenzoic acid (610-28-6)

Conditions	Yield
With nitric acid at 145℃; im Druckrohr;
With nitric acid
With potassium dichromate
With potassium permanganate

2,5-dinitrotoluene (619-15-8) → 2,3,6-trinitrotoluene (18292-97-2)

Conditions	Yield
Nitrierung;

2,5-dinitrotoluene (619-15-8) → 2,3,6-trinitrotoluene (18292-97-2) + 2,4,5-trinitrotoluene (610-25-3)

Conditions	Yield
With sulfuric acid; nitric acid at 80 - 120℃;

2,5-dinitrotoluene (619-15-8) → 2,4,5-trinitrotoluene (610-25-3)

Conditions	Yield
With sulfuric acid; nitric acid at 95℃;
Nitrierung;

2,5-dinitrotoluene (619-15-8) → 2-nitroso-5-nitrotoluene (57610-10-3)

Conditions	Yield
With potassium hydroxide; hydroxylamine durch Ansaeuern mit Salzsaeure;

2,5-dinitrotoluene (619-15-8) → 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
With hydrogenchloride; 4-nitro-3-methylaniline; tin(ll) chloride at 7℃;
Stage #1: 2,5-dinitrotoluene With iron; acetic acid; tin(ll) chloride at 85℃; for 0.5h; Stage #2: With hydrogenchloride for 0.833333h; Temperature;

2,5-dinitrotoluene (619-15-8) → 4-nitro-3-methylaniline (611-05-2) + 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
With ammonia at 150℃;
With ethanol; ammonia at 150℃;
With hydrogenchloride; ethanol; tin(ll) chloride at 7℃;

2,5-dinitrotoluene (619-15-8) → bis-(2-methyl-4-nitro-phenyl)-diazene-N-oxide (5805-94-7)

Conditions	Yield
With potassium hydroxide; hydroxylamine nachfolgendes Ansaeuern;

2,5-dinitrotoluene (619-15-8) + benzaldehyde (100-52-7) → 2,5-dinitro-stilbene

Conditions	Yield
With piperidine at 165 - 175℃;

2,5-dinitrotoluene (619-15-8) + 4-dimethylamino-benzaldehyde (100-10-7) → dimethyl-(2'.5'-dinitro-trans-stilbenyl-(4))-amine

Conditions	Yield
With piperidine at 170℃;

2,5-dinitrotoluene (619-15-8) → 2,5-dinitrobenzyl bromide (67567-47-9)

Conditions	Yield
With bromine; dibenzoyl peroxide In tetrachloromethane Irradiation;

Upstream product

• 56207-39-7 2-methyl-3,6-dinitro-aniline 
• 101084-63-3 4-methyl-2,5-dinitro-benzoic acid 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 7697-37-2 nitric acid 
• 99-08-1 1-methyl-3-nitrobenzene 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 36164-91-7 toluquinone dioxime 
• 60-29-7 diethyl ether 
• 10544-72-6 dinitrogen tetraoxide 
• 7647-01-0 hydrogenchloride 
• 408328-19-8 2-nitro-5-nitrosotoluene 
• 603-83-8 3-nitro-o-tolylamine 
• 108-88-3 toluene 

Downstream Products

• 83759-95-9 1-(ethylsulfanyl)-2-methyl-4-nitrobenzene 
• 611-05-2 4-nitro-3-methylaniline 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 108-71-4 3,5-diaminotoluene 
• 823-40-5 2,6-toluenediamine 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 95-70-5 2-methyl-p-phenylenediamine 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 2719-15-5 2-methyl-4-nitroacetanilide 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 
• 5805-94-7 bis-(2-methyl-4-nitro-phenyl)-diazene-N-oxide 
• 57610-10-3 2-nitroso-5-nitrotoluene 
• 610-25-3 2,4,5-trinitrotoluene 

Relevant articles and documents

Synthesis method of 2-methyl-4-nitrobenzoic acid

The invention discloses a synthesis method of 2-methyl-4-nitrobenzoic acid, and belongs to the technical field of chemosynthesis. According to the method, methylbenzene is used as raw materials; reaction liquid formed by mixing concentrated nitric acid and concentrated sulfuric acid is added for mixing; after being washed by a sodium hydroxide solution, the materials take an reaction with stannous chloride, iron powder and glacial acetic acid; then, hydrochloric acid is dropwise added for mixing to obtain 2-amino-5-nitrotoluene; then, the 2-amino-5-nitrotoluene is mixed with acetic acid and the concentrated sulfuric acid for taking a reaction; after the oxidization by an oxidizing agent of sodium perborate, temperature lowering by ice water and washing by deionized water are carried out; then, under the oxidization effect of an oxidizing agent of potassium permanganate, the materials are mixed with hydrochloric acid for reaction; then, still standing, suction filtering and drying are carried out, and the 2-methyl-4-nitrobenzoic acid is obtained. The synthesis method has the beneficial effects that the synthesis process is simple; the cost is low; byproducts are few; the yield of obtained products is as high as more than 95 percent; the purity is as high as more than 99 percent.

Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: A photoelectron spectroscopy and ab initio investigation

We present an investigation of the close relationship between chemical structure, physical properties and reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation we: (i) point out that accurate ab initio calculations play a key role in the complete assignment of photoemission measurements, as well as in the estimate of proton affinities in the case of all the eligible sites; (ii) revisit, at a more quantitative level, textbook models based on inductive and resonant effects of different substituents of the aromatic ring, as well as on the hyper-conjugative connection of the methyl group to the π-conjugated system; (iii) provide an accurate analysis of correlation patterns between calculated proton affinities and core-ionization energies, which represent a powerful tool, capable of predicting site-specific reactivities of polysubstituted molecules in the case of electrophilic aromatic substitution reactions.

PROCESS FOR THE PREPARATION OF NITRATED AROMATICS AND MIXTURES THEREOF

A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO3)3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO3)3, leads to simplifications of the process and improved yields.