67827-72-9

Basic information

• Product Name: 2-Methoxy-5-nitroaniline hydrochloride
• Synonyms: 5-Nitro-o-anisidine hydrochloride (NH2=1);2-Methoxy-5-nitroaniline hydrochloride;4-Nitro-2-aminoanisole hydrochloride;2-Methoxy-5-nitroaniline, monohydrochloride;2-Methoxy-5-nitrobenzenamine, hydrochloride;Benzenamine, 2-methoxy-5-nitro-, hydrochloride (1:1);Einecs 267-234-5;2-methoxy-5-nitro-benzenamin monohydrochlo
• CAS NO: 67827-72-9
• Molecular Formula: C₇H₈N₂O₃*ClH
• Molecular Weight: 204.61
• EINECS: 267-234-5
• Mol File: 67827-72-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 351.8 °C at 760 mmHg
• Flash Point: 166.6 °C
• Appearance: /
• Density: 1.318[at 20℃]
• Vapor Pressure: 4.01E-05mmHg at 25°C
• Water Solubility: 297g/L at 25℃
• CAS DataBase Reference: 2-Methoxy-5-nitroaniline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-nitroaniline hydrochloride(67827-72-9)
• EPA Substance Registry System: 2-Methoxy-5-nitroaniline hydrochloride(67827-72-9)

Safety Data

• Hazardous Substances Data: 67827-72-9(Hazardous Substances Data)

Usage

Flammability and Explosibility

Flammable

InChI:InChI=1/C7H8N2O3.ClH/c1-12-7-3-2-5(9(10)11)4-6(7)8;/h2-4H,8H2,1H3;1H

Synthetic route

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) + acetic anhydride (108-24-7) → N-(2-methoxy-5-nitrophenyl)acetamide (33721-54-9)

Conditions	Yield
at 80℃; for 8h;	93.48%

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → 3-amino-4-methoxynitrobenzene (99-59-2)

Conditions	Yield
With sodium hydroxide In water pH=8;	83.7%

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C9H9IN2O4

Conditions	Yield
Multi-step reaction with 3 steps 1: 8 h / 80 °C 2: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3: potassium iodide / N,N-dimethyl-formamide / 8 h / 120 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → acetic acid-(2,3-dimethoxy-5-nitro-anilide)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: potassium iodide / N,N-dimethyl-formamide / 8 h / 120 °C 4.1: copper(l) iodide / methanol; 1,4-dioxane / 12 h / 90 °C 4.2: 4 h / 80 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C9H11BrN2O2

Conditions	Yield
Multi-step reaction with 3 steps 1: 8 h / 80 °C 2: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3: iron; acetic acid / 6 h / 75 - 80 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C15H16BrNO4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C13H14BrNO3

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → triethyl 4-bromo-5-methoxy-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → 4,5-dimethoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylic acid (81770-66-3)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / methanol; 1,4-dioxane / 8 h / Reflux View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → triethyl 4-ethoxy-5-methoxy-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / 1,4-dioxane / 8 h / Reflux View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → 2-ethyl 7,9-dimethyl 4-bromo-5-methoxy-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → 4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid (79127-57-4)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / methanol; 1,4-dioxane / 8 h / Reflux 8.1: acetic acid; hydrogen iodide / 8 h / Reflux View Scheme
Multi-step reaction with 9 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / 1,4-dioxane / 8 h / Reflux 8.1: sodium hydroxide / 6 h / Reflux 9.1: acetic acid; hydrogen iodide / 8 h / Reflux View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → pyrroloquinoline quinone (72909-34-3)

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / 1,4-dioxane / 8 h / Reflux 8.1: sodium hydroxide / 6 h / Reflux 9.1: acetic acid; hydrogen iodide / 8 h / Reflux 10.1: dihydrogen peroxide / 24 h / 35 °C View Scheme
Multi-step reaction with 9 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / methanol; 1,4-dioxane / 8 h / Reflux 8.1: acetic acid; hydrogen iodide / 8 h / Reflux 9.1: dihydrogen peroxide / 24 h / 35 °C View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C17H14N2O8

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 8 h / 80 °C 2.1: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice 3.1: iron; acetic acid / 6 h / 75 - 80 °C 4.1: hydrogenchloride / water / 1 h / -25 °C 4.2: 0.25 h / -10 °C 5.1: hydrogenchloride / water; ethanol / 8 h / Reflux 6.1: dichloromethane / 24 h / 20 °C 7.1: copper(l) iodide / 1,4-dioxane / 8 h / Reflux 8.1: sodium hydroxide / 6 h / Reflux View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C9H9BrN2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: 8 h / 80 °C 2: methanesulfonic acid; N-Bromosuccinimide / 12 h / 25 °C / Cooling with ice View Scheme

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → C9H9ClN2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: 8 h / 80 °C 2: sulfuric acid; N-chloro-succinimide / 36 h / 50 °C / Cooling with ice View Scheme

Downstream Products

• 99-59-2 3-amino-4-methoxynitrobenzene 
• 72909-34-3 pyrroloquinoline quinone 
• 79127-57-4 4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid 
• 33721-54-9 N-(2-methoxy-5-nitrophenyl)acetamide