6313-37-7

Basic information

• Product Name: 2,5-Dimethoxy-4-nitroaniline
• Synonyms: TIMTEC-BB SBB000371;2,5-DIMETHOXY-4-NITROANILINE;2,5-DIMETHOXY-4-NITROBENZENAMINE;2,5-dimethoxy-4-nitro-benzenamin;2,5-DIMETHOXY-4-NITROANILINE, 98+%;Benzenamine, 2,5-dimethoxy-4-nitro-
• CAS NO: 6313-37-7
• Molecular Formula: C₈H₁₀N₂O₄
• Molecular Weight: 198.18
• EINECS: 228-640-8
• Product Categories: Amines;C8;Nitrogen Compounds
• Mol File: 6313-37-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 152-155 °C(lit.)
• Boiling Point: 335.48°C (rough estimate)
• Flash Point: 196.6 °C
• Appearance: Dark khaki/Granular Crystalline Powder
• Density: 1.3764 (rough estimate)
• Vapor Pressure: 1.17E-06mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• PKA: 0.60±0.14(Predicted)
• CAS DataBase Reference: 2,5-Dimethoxy-4-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxy-4-nitroaniline(6313-37-7)
• EPA Substance Registry System: 2,5-Dimethoxy-4-nitroaniline(6313-37-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6313-37-7(Hazardous Substances Data)

Usage

Chemical Properties

dark khaki granular crystalline powder

General Description

2,5-Dimethoxy-4-nitroaniline was used in screening of enzyme arylamine N-acetyltransferase isolated from Bacillus cereus.

InChI:InChI=1/C8H10N2O4/c1-13-7-4-6(10(11)12)8(14-2)3-5(7)9/h3-4H,9H2,1-2H3

Synthetic route

N-(2,5-dimethoxy-4-nitrophenyl)thiobenzamide (262436-38-4) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
With hydrogen carbonate In methanol for 24h; Deacylation; Heating;	100%

1,4-dimethoxy-2-nitrobenzene (89-39-4) → 2,5-dimethoxy-4-nitroaniline (6313-37-7) + 2-amino-3-nitrohydroquinone dimethylether (26002-57-3)

Conditions	Yield
Stage #1: 1,4-dimethoxy-2-nitrobenzene With pyridine; trifluorormethanesulfonic acid; lithium perchlorate In acetonitrile at 25℃; Electrochemical reaction; Stage #2: With piperidine In acetonitrile at 80℃; for 12h; Electrochemical reaction; Overall yield = 95 %;	A 66% B 30%

pyridine (110-86-1) + 1,4-dimethoxy-2-nitrobenzene (89-39-4) → 2,5-dimethoxy-4-nitroaniline (6313-37-7) + 2-amino-3-nitrohydroquinone dimethylether (26002-57-3)

Conditions	Yield
Stage #1: pyridine; 1,4-dimethoxy-2-nitrobenzene With ammonium peroxydisulfate; tris(1,10-phenathrolinyl)ruthenium(II) hexafluorophosphate In water; acetonitrile at 23℃; for 24h; Irradiation; Inert atmosphere; Schlenk technique; Stage #2: With pyrrolidine at 70℃; for 12h;	A 13% B 41 mg

2,5-dimethoxy-4-nitroacetanilide (25445-13-0) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
durch Verseifen;
With hydrogenchloride

N,N'-bis-(2,5-dimethoxy-4-nitro-phenyl)-urea (108851-78-1) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
With ammonium hydroxide at 150℃;

4-chloro-5-nitro-2-amino-phenol-methyl ether → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
With potassium carbonate

C18H26N2O8 → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
With potassium carbonate In methanol Heating;

N-(2,5-Dimethoxyphenyl)benzamide (135-45-5) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / HNO3; H2O / acetic acid / 1.5 h / 20 °C 2: 79 percent / Lawesson's reagent / toluene / 12 h / 80 °C 3: 100 percent / HCO3(-) / methanol / 24 h / Heating View Scheme

N-(2,5-Dimethoxy-4-nitrophenyl)benzamide (92-20-6) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / Lawesson's reagent / toluene / 12 h / 80 °C 2: 100 percent / HCO3(-) / methanol / 24 h / Heating View Scheme

1,3-bis(2,5-dimethoxyphenyl)urea (1240-72-8) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous nitric acid <86 percent >; acetic acid 2: aqueous ammonia / 150 °C View Scheme

2,5-dimethoxyacetanilide (3467-59-2) → 2,5-dimethoxy-4-nitroaniline (6313-37-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; nitric acid / 5 °C 2: alcoholic hydrochloric acid View Scheme

2,5-dimethoxy-4-nitroaniline (6313-37-7) + Ethyl oxalyl chloride (4755-77-5) → ethyl N-(2,5-dimethoxy-4-nitrophenyl)oxanilate (92643-78-2)

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide Ambient temperature;	95.6%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2,5-dimethoxy-4-nitroaniline (6313-37-7) → 1-(2,5-Dimethoxy-4-nitro-phenyl)-1H-pyrrole (186390-73-8)

Conditions	Yield
With acetic acid for 0.166667h; Heating;	91%

2,5-dimethoxy-4-nitroaniline (6313-37-7) → 2,5-dimethoxy-p-phenylenediamine (17626-02-7)

Conditions	Yield
With hydrogen; platinum on activated charcoal In ethanol under 1520.1 Torr; for 15h; Reduction;	88%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 16h;

2,5-dimethoxy-4-nitroaniline (6313-37-7) → 4-chloro-2,5-dimethoxy nitrobenzene (6940-53-0)

Conditions	Yield
Stage #1: 2,5-dimethoxy-4-nitroaniline With acetic acid; isopentyl nitrite at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; copper(l) chloride In water at 0 - 80℃; Inert atmosphere;	79%
Stage #1: 2,5-dimethoxy-4-nitroaniline With sulfuric acid; sodium nitrite In acetic acid at 40℃; for 0.5h; Diazotization; Stage #2: With copper(l) chloride In hydrogenchloride at 80℃; for 20h; Chlorination;	70%
Stage #1: 2,5-dimethoxy-4-nitroaniline With sulfuric acid; acetic acid; sodium nitrite at 40℃; for 0.5h; Diazotization; Stage #2: With hydrogenchloride; copper(l) chloride at 80℃; for 0.333333h; Substitution;
With hydrogenchloride; copper(l) chloride at 80℃; Diazotization;

2,5-dimethoxy-4-nitroaniline (6313-37-7) + O-benzoyl cyclobutanone oxime → 4-((2,5-dimethoxy-4-nitrophenyl)amino)butanenitrile

Conditions	Yield
With bis(2,2,6,6-tetramethyl-3,5-heptadionato) copper(II) In N,N-dimethyl-formamide at 80℃; for 12h; Schlenk technique; Inert atmosphere;	70%

2,5-dimethoxy-4-nitroaniline (6313-37-7) + trans-1-chlorocarbonyl-4-(methoxycarbonyl)-cyclohexane (32529-80-9, 36218-60-7) → methyl (1r,4r)-4-[(2,5-dimethoxy-4-nitro-phenyl)carbamoyl]cyclohexanecarboxylate

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;	55%

2,5-dimethoxy-4-nitroaniline (6313-37-7) + 2,3,5,6-tetrafluoroanisole (2324-98-3)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium tert-butylate; oxygen; copper diacetate In N,N-dimethyl-formamide at 40℃; for 24h;	52%

Conditions	Yield
With barium carbonate In 1,2-dichloro-ethane Ambient temperature;	45.8%
With barium carbonate In 1,2-dichloro-ethane at 20℃;

Conditions	Yield
In chloroform Reflux;	42%

2-furancarbonyl chloride (527-69-5) + 2,5-dimethoxy-4-nitroaniline (6313-37-7) → Furan-2-carboxylic acid (2,5-dimethoxy-4-nitro-phenyl)-amide (917561-76-3)

Conditions	Yield
In tetrahydrofuran Heating;
With tetrachloromethane; sodium carbonate; acetone

2,5-dimethoxy-4-nitroaniline (6313-37-7) + 4-nitrophenoxyacetic acid (1798-11-4) → (4-nitro-phenoxy)-acetic acid-(2,5-dimethoxy-4-nitro-anilide)

2,5-dimethoxy-4-nitroaniline (6313-37-7) + (2-chloro-phenoxy)-acetyl chloride (20143-41-3) → (2-chloro-phenoxy)-acetic acid-(2,5-dimethoxy-4-nitro-anilide)

Conditions	Yield
With pyridine

2,5-dimethoxy-4-nitroaniline (6313-37-7) → 1-bromo-2,5-dimethoxy-4-nitrobenzene (98545-68-7)

Conditions	Yield
With hydrogen bromide Diazotization.Erwaermen des Diazoniumsalzes mit Kupfer(I)-bromid und Bromwasserstoffsaeure;

2,5-dimethoxy-4-nitroaniline (6313-37-7) → 2,5-dimethoxy-4,N-dinitro-aniline

Conditions	Yield
With sodium nitrite beim aufeinanderfolgenden Behandeln mit wss.Salzsaeure, wss.Natronlauge und wss.Natriumhypochlorit-Loesung;
With sodium nitrite beim aufeinanderfolgenden Behandeln mit wss.Salzsaeure, wss.Natronlauge und wss.Natriumhypochlorit-Loesung;

2,5-dimethoxy-4-nitroaniline (6313-37-7) + N,N-dimethyl-aniline (121-69-7) → N,N'-bis-(2,5-dimethoxy-4-nitro-phenyl)-urea (108851-78-1)

Conditions	Yield
With toluene

2,5-dimethoxy-4-nitroaniline (6313-37-7) + cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexanecarboxylic acid-(2,5-dimethoxy-4-nitro-anilide)

Conditions	Yield
With potassium carbonate; benzene

formic acid (64-18-6) + 2,5-dimethoxy-4-nitroaniline (6313-37-7) → 1-Isocyano-2,5-dimethoxy-4-nitro-benzene

Conditions	Yield
(i), (ii) COCl2, Et3N; Multistep reaction;

2,5-dimethoxy-4-nitroaniline (6313-37-7) + dimethyl sulfate (77-78-1) → 4-Nitro-2,5-dimethoxy-1-methylmercapto-benzol (90610-66-5)

Conditions	Yield
Multistep reaction;

2,5-dimethoxy-4-nitroaniline (6313-37-7) + diethyl oxaloacetate (108-56-5) → 2-(4-Nitro-2,5-dimethoxy-phenylimino)-bernsteinsaeure-1-ethylester-4-(4-nitro-2,5-dimethoxy-anilid) (96308-96-2)

Conditions	Yield
at 150 - 160℃;

2,5-dimethoxy-4-nitroaniline (6313-37-7) + acetic anhydride (108-24-7) → 2,5-dimethoxy-4-nitroacetanilide (25445-13-0)

Conditions	Yield
With pyridine at 20℃; for 24h; Acylation;

hydrogenchloride (7647-01-0) + 2,5-dimethoxy-4-nitroaniline (6313-37-7) + sodium nitrite + aqueous NaOH-solution + aqueous sodium hypochlorite → 2,5-dimethoxy-4,N-dinitro-aniline

2,5-dimethoxy-4-nitroaniline (6313-37-7) + di-tert-butyl dicarbonate (24424-99-5) → C18H26N2O8

Conditions	Yield
With dmap In tetrahydrofuran Heating;

Upstream product

• 110-86-1 pyridine 
• 89-39-4 1,4-dimethoxy-2-nitrobenzene 
• 3467-59-2 2,5-dimethoxyacetanilide 
• 1240-72-8 1,3-bis(2,5-dimethoxyphenyl)urea 
• 92-20-6 N-(2,5-Dimethoxy-4-nitrophenyl)benzamide 
• 135-45-5 N-(2,5-Dimethoxyphenyl)benzamide 
• 262436-38-4 N-(2,5-dimethoxy-4-nitrophenyl)thiobenzamide 
• 108851-78-1 N,N'-bis-(2,5-dimethoxy-4-nitro-phenyl)-urea 
• 25445-13-0 2,5-dimethoxy-4-nitroacetanilide 

Downstream Products

• 98545-68-7 2-bromo-1,4-dimethoxy-5-nitrobenzene 
• 108851-78-1 N,N'-bis-(2,5-dimethoxy-4-nitro-phenyl)-urea 
• 92643-78-2 ethyl N-(2,5-dimethoxy-4-nitrophenyl)oxanilate 
• 186390-73-8 1-(2,5-Dimethoxy-4-nitro-phenyl)-1H-pyrrole 
• 25445-13-0 2,5-dimethoxy-4-nitroacetanilide 
• 17626-02-7 2,5-dimethoxy-p-phenylenediamine 
• 1242434-82-7 N-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-2,5-dimethoxy-4-nitrobenzenamine 
• 96308-96-2 2-(4-Nitro-2,5-dimethoxy-phenylimino)-bernsteinsaeure-1-ethylester-4-(4-nitro-2,5-dimethoxy-anilid) 
• 90610-66-5 4-Nitro-2,5-dimethoxy-1-methylmercapto-benzol 
• 6940-53-0 4-chloro-2,5-dimethoxy nitrobenzene 
• 917561-76-3 Furan-2-carboxylic acid (2,5-dimethoxy-4-nitro-phenyl)-amide 
• 876016-76-1 N-(2,5-dimethoxy-4-nitrophenyl)acrylamide 

Relevant articles and documents

Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations

We report the photocatalytic C-H amination of aromatics overcoming redox potential limitations. Radical cations of aromatic compounds are generated photocatalytically using Ru(phen)3(PF6)2, which has a reduction potential at a high oxidation state (Ered(RuIII/RuII) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates (Eox = +1.65 to +2.27 V vs SCE). The radical cations are trapped with pyridine to give N-arylpyridinium ions, which were converted to aromatic amines.

An improved synthesis of N-Boc protected aryl amines

There are several known methods of protecting amines as their Boc derivatives. For less nucleophilic amines such as aryl amines these methods often give poor yields and are generally not satisfactory. Here, Boc aryl amines are obtained by first introducing two Boc groups followed by selective removal of one of them. This procedure works well for a number highly sterically hindered substrates as well as electron deficient and electron rich aryl amines.