610-39-9

Basic information

• Product Name: 3,4-DINITROTOLUENE
• Synonyms: 1,2-Dinitro4-methylbenzene;3,4-dinitro-toluen;3,4-DNT;4-methyl-1,2-dinitro-benzen;4-Methyl-1,2-dinitrobenzene;benzene,1-methyl-3,4-dinitro-;Benzene,4-methyl-1,2-dinitro-;Toluene, 3,4-dinitro-
• CAS NO: 610-39-9
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13
• EINECS: 210-222-1
• Product Categories: Intermediates of Dyes and Pigments;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 610-39-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 54-57 °C(lit.)
• Boiling Point: 320.51°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.2594
• Vapor Pressure: 8.66E-05mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• CAS DataBase Reference: 3,4-DINITROTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DINITROTOLUENE(610-39-9)
• EPA Substance Registry System: 3,4-DINITROTOLUENE(610-39-9)

Safety Data

• Hazard Codes: T,N
• Statements: 45-23/24/25-48/22-51/53-62-68
• Safety Statements: 53-45-61
• RIDADR: UN 3454 6.1/PG 2
• WGK Germany: 3
• RTECS: XT2100000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 610-39-9(Hazardous Substances Data)

Usage

General Description

Yellow to red solid or heated liquid with a slight odor. Solidifies in cool water. Solid and liquid sink in water .

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3,4-DINITROTOLUENE may explode when exposed to heat or flame [USCG, 1999].

Health Hazard

INHALATION, INGESTION OR SKIN ABSORPTION: Headache, weakness, nausea or dizziness, cyanosis, drowsiness, shortness of breath and collapse. EYES AND SKIN: Can burn eyes and skin.

Safety Profile

Moderately toxic by ingestion. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of NOx. See also 2,4 DINITROTOLUENE.

Purification Methods

Steam distil it and crystallise it from *C6H6/pet ether. Store it with 10% of H2O to avoid EXPLOSION.[Beilstein 5 H 341, 5 III 761, 5 IV 866.]

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

Synthetic route

4-methyl-2-nitroaniline (89-62-3) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Stage #1: 4-methyl-2-nitroaniline With sulfuric acid; sodium nitrite In water for 0.333333h; cooling; Stage #2: With sodium hydrogencarbonate; sodium nitrite In water at 10 - 20℃; for 0.166667h; Further stages.;	92%
With caro's acid Oxydation mit rauchender Salpetersaeure;
Diazotization.Behandlung der Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;

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) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
bei der Nitrierung;
Nitrierung;
durch Nitrierung;

4-methyl-2-nitroacetanilide (612-45-3) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With dihydrogen peroxide; acetic acid

4-methyl-2-nitro-1-nitrosobenzene (6971-33-1) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With dihydrogen peroxide; nitric acid; acetic acid
With nitric acid
With nitric acid
With nitric acid for 0.0833333h;	8 g

5-methyl-2-nitroaniline (578-46-1) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;

2,3-dinitro-6-methylaniline (3484-29-5) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With ethanol; sulfuric acid; sodium nitrite

3,4-dinitro-6-methylaniline (70343-04-3) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With ethanol; sulfuric acid; sodium nitrite

2,3-dinitro-5-methylaniline (70343-07-6) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With ethanol; sulfuric acid; sodium nitrite

2-nitro-4-methylbenzene diazonium tetrafluoroborate → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
With sodium nitrite In water at 40.1 - 56.9℃; Kinetics;

1-methyl-3-nitrobenzene (99-08-1) → 3,4-Dinitrotoluene (610-39-9) + 2.3-dinitro-toluene, 2.5-dinitro-toluene

Conditions	Yield
durch Nitrierung;

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℃;

4-methyl-2-nitro-1-nitrosobenzene (6971-33-1) + nitric acid (7697-37-2) → 3,4-Dinitrotoluene (610-39-9)

3,5-dinitrotoluene (618-85-9) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: alcohol; ammonium sulfide 3: concentrated sulfuric acid; nitric acid / <9 4: aqueous alcoholic sulfuric acid 5: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme

N-(2-methyl-5-nitrophenyl)acetamide (2879-79-0) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid / Erhitzen des Reaktionsprodukts mit verd.Schwefelsaeure 2: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; nitric acid / Erhitzen des Reaktionsprodukts mit verd.Schwefelsaeure 2: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme

3-methyl-5-nitro-aniline (618-61-1) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 4 steps 2: concentrated sulfuric acid; nitric acid / <9 3: aqueous alcoholic sulfuric acid 4: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme

acetic acid-(3-methyl-5-nitro-anilide) (69112-72-7) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; nitric acid / <9 2: aqueous alcoholic sulfuric acid 3: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme

acetic acid-(5-methyl-2,3-dinitro-anilide) (861297-21-4) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alcoholic sulfuric acid 2: absolute alcohol; fuming sulfuric acid; sodium nitrite View Scheme

3-Methylacetanilide (537-92-8) → 3,4-Dinitrotoluene (610-39-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid; nitric acid / und Erhitzen des Reaktionsprodukts mit wss.Schwefelsaeure 2: Diazotization.Behandlung der Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit View Scheme

toluene (108-88-3) → 2,4-dinitrotoluene (121-14-2) + 3,5-dinitrotoluene (618-85-9) + 2,6-dinitrotoluene (606-20-2) + 3,4-Dinitrotoluene (610-39-9) + 2,5-dinitrotoluene (619-15-8)

Conditions	Yield
With ferric nitrate pentahydrate; nitric acid at 100℃; for 99h;

3,4-Dinitrotoluene (610-39-9) → 3,4-dinitrobenzoic acid (528-45-0)

Conditions	Yield
With oxygen; ozone; acetic acid; cobalt(II) acetate at 100℃;	97.6%
With chromium(VI) oxide; sulfuric acid 1.) 35 deg C, 0.5 h, 2.) 45-55 deg C, 4 h;	75%
With nitric acid at 140℃;

propan-1-ol (71-23-8) + 3,4-Dinitrotoluene (610-39-9) → 2-ethyl-6-methylbenzimidazole

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	97%

3,4-Dinitrotoluene (610-39-9) → 4-methyl-1,2-diaminobenzene (496-72-0)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 48h;	96.6%
With hydrogen In methanol at 50℃; under 1500.15 Torr; for 0.25h; Inert atmosphere;	88%
With 5 wt% ruthenium/carbon; hydrogen; sodium nitrite In isopropyl alcohol at 150℃; under 62256.2 Torr; for 4h; Temperature; Autoclave;

formic acid (64-18-6) + 3,4-Dinitrotoluene (610-39-9) → 5-methylbenzimidazole (614-97-1)

Conditions	Yield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction;	96%

ethanol (64-17-5) + 3,4-Dinitrotoluene (610-39-9) → 2,6-dimethyl-1H-benzo[d]imidazole (1792-41-2)

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	95%

3,4-Dinitrotoluene (610-39-9) → 3,4-dinitrobenzo trichloride (76213-13-3)

Conditions	Yield
With hypochlorous anhydride In tetrachloromethane at 75℃;	89%

3,4-Dinitrotoluene (610-39-9) + Tris(3,6-dioxaheptyl)amine (70384-51-9) + N,N-dimethylethylenediamine (108-00-9) → N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamine (138423-04-8) + N,N,N-Trimethyl-2-(5-methyl-2-nitroanilino)ethanaminium Iodide (144674-99-7)

Conditions	Yield
In dimethyl sulfoxide	A 80% B n/a

3,4-Dinitrotoluene (610-39-9) + orthobenzoic acid trimethyl ester (707-07-3) → 5-methyl-2-phenyl-1H-1,3-benzimidazole (2963-65-7)

Conditions	Yield
With indium; acetic acid In ethyl acetate for 4h; Reflux; Inert atmosphere;	58%

3,4-Dinitrotoluene (610-39-9) → 5-methyl-2-nitroaniline (578-46-1)

Conditions	Yield
With formic acid; triethylamine; palladium on activated charcoal at 100℃; for 1h;	55%
With urea; tetramethylurea at 110℃;

Trimethyl orthoacetate (1445-45-0) + 3,4-Dinitrotoluene (610-39-9) → 2,5-dimethylbenzimidazole (1792-41-2)

Conditions	Yield
With indium; acetic acid In ethyl acetate for 4.5h; Reflux; Inert atmosphere;	53%

3,4-Dinitrotoluene (610-39-9) + rac-Ala-OH (302-72-7) → D,L-N-(5-methyl-2-nitrophenyl)alanine (639474-96-7)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 150℃; for 0.5h;	49.7%

3,4-Dinitrotoluene (610-39-9) + acetone (67-64-1) → 2,2,4,7-tetramethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine + C10H14N2 + 2,2,4,8-tetramethyl-2,3-dihydro-1H-1,5-benzodiazepine

Conditions	Yield
With 0.2 wt% Pt/TiO2; hydrogen at 55 - 65℃; under 5250.53 Torr; for 3.25h;	A n/a B 7% C n/a

3,4-Dinitrotoluene (610-39-9) → 3-nitrotoluene-4-sulfonic acid (65542-35-0)

Conditions	Yield
With sodium sulfite In water Substitution; Heating;	4%

3,4-Dinitrotoluene (610-39-9) + potassium phenolate (100-67-4) → 4-methyl-1-nitro-2-phenoxybenzene (60287-60-7)

Conditions	Yield
With phenol

3,4-Dinitrotoluene (610-39-9) + sodium methylate (124-41-4) → 3-methoxy-4-nitrotoluene (38512-82-2)

3,4-Dinitrotoluene (610-39-9) + semicarbazide hydrochloride (563-41-7) → 1-(5-methyl-2-nitro-phenyl)-semicarbazide

Conditions	Yield
With ethanol; sodium acetate

3,4-Dinitrotoluene (610-39-9) → 5-methyl-3H-benzotriazole-1-oxide + 5-methyl-2-nitrophenylhydrazine (56637-42-4)

Conditions	Yield
With ethanol; hydrazine hydrate

3,4-Dinitrotoluene (610-39-9) → 2,3,4-trinitrotoluene (602-29-9)

Conditions	Yield
Nitrierung;

3,4-Dinitrotoluene (610-39-9) → 2,3,4-trinitrotoluene (602-29-9) + 2,4,5-trinitrotoluene (610-25-3)

Conditions	Yield
With sulfuric acid; nitric acid

3,4-Dinitrotoluene (610-39-9) → 2,4,5-trinitrotoluene (610-25-3)

Conditions	Yield
With sulfuric acid; nitric acid at 95℃;
Nitrierung;
With sulfuric acid; nitric acid at 80 - 90℃; for 0.5h;

3,4-Dinitrotoluene (610-39-9) → (5,5'-dimethyl-2,2'-dinitrophenyl)disulfide (52062-85-8)

Conditions	Yield
With methanol; sodium sulfide; sulfur

3,4-Dinitrotoluene (610-39-9) → 4-methyl-2-nitro-1-nitrosobenzene (6971-33-1)

Conditions	Yield
With potassium hydroxide; hydroxylamine Behandeln mit Wasser und Ansaeuern mit Salzsaeure;

3,4-Dinitrotoluene (610-39-9) → 4-methyl-2-nitro-1-nitrosobenzene (6971-33-1) + 5-methyl-2-nitronitrosobenzene (474318-51-9)

Conditions	Yield
With methanol; hydroxylamine

3,4-Dinitrotoluene (610-39-9) → 4-methyl-2-nitroaniline (89-62-3)

Conditions	Yield
With methanol; ammonia at 150℃; unter Druck;

3,4-Dinitrotoluene (610-39-9) → 5-methyl-2-nitroaniline (578-46-1) + 4-methyl-2-nitroaniline (89-62-3)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride at 7℃;
With methanol; ammonia at 150℃; unter Druck;

Upstream product

• 618-85-9 3,5-dinitrotoluene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 537-92-8 3-Methylacetanilide 
• 861297-21-4 acetic acid-(5-methyl-2,3-dinitro-anilide) 
• 69112-72-7 acetic acid-(3-methyl-5-nitro-anilide) 
• 618-61-1 3-methyl-5-nitro-aniline 
• 2879-79-0 N-(2-methyl-5-nitrophenyl)acetamide 
• 6971-33-1 4-methyl-2-nitro-1-nitrosobenzene 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 89-62-3 4-methyl-2-nitroaniline 
• 70343-07-6 2,3-dinitro-5-methylaniline 
• 70343-04-3 3,4-dinitro-6-methylaniline 

Downstream Products

• 313266-23-8 4-diacetoxymethyl-1,2-dinitro-benzene 
• 858784-79-9 N-methyl-N-(5-methyl-2-nitro-phenyl)-hydrazine 
• 4600-08-2 4,N-dimethyl-2-nitroaniline 
• 65081-42-7 3-(N-methylamino)-4-nitrotoluene 
• 119-10-8 4-methoxy-3-nitrotoluene 
• 38512-82-2 3-methoxy-4-nitrotoluene 
• 578-46-1 5-methyl-2-nitroaniline 
• 76213-13-3 3,4-dinitrobenzo trichloride 
• 6971-33-1 4-methyl-2-nitro-1-nitrosobenzene 
• 474318-51-9 5-methyl-2-nitronitrosobenzene 
• 26198-27-6 5-methyl-1H-benzo[d][1,2,3]triazol-1-ol 
• 56637-42-4 5-methyl-2-nitrophenylhydrazine 
• 89-62-3 4-methyl-2-nitroaniline 
• 496-72-0 4-methyl-1,2-diaminobenzene 

Relevant articles and documents

An "ortho effect" in electrophilic aromatic nitrations: Theoretical analysis and experimental validation

Usually, a π-donor substituent acts as an ortho/para directing group in an electrophilic aromatic substitution reaction, and a π-acceptor substituent acts as a meta directing group. Interestingly, when a π-acceptor substituent is meta to a π-donor substituent, certain electrophilic aromatic nitration occurs ortho to the π-acceptor substituent rather than para . The "ortho effect", highlighted in various textbooks, has been tentatively analyzed here based on ab initio calculations. The reliability of the calculations was verified by the corresponding experimental data, including a newly-designed electrophilic aromatic nitration that also gave reasonable product distributions.

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.

6-Lithioquinoxalines and Their Transformations

6-Bromo-2,3-diphenylquinoxaline reacts with butyllithium to give the 6-lithio derivative in a yield of more than 80%, which reacts with electrophiles such as benzophenone, Michler ketone, methyl ethyl ketone, iodine, selenium, and dimethylformamide to give the corresponding quinoxaline derivatives. 6-Bromo-2,3-dimethylquinoxaline is metallated with butyl- and phenyllithium at the methyl groups and benzene ring. These organolithium compounds react with benzophenone to give the corresponding diphenyl- and triaryl-carbinols, whose yield and ratio were determined by HPLC. These results open prospects for preparing new quinoxaline derivatives substituted at the annelated benzene ring.