119-81-3

Basic information

• Product Name: 4-METHOXY-2-NITROACETANILIDE
• Synonyms: 2-nitro-p-acetanisidid;n-(4-methoxy-2-nitrophenyl)-acetamid;p-Acetaniside, 2'-nitro-;p-Acetanisidide, 2'-nitro-;p-Acetanisidide, 2-nitro-;N-ACETYL-4-METHOXY-2-NITROANILINE;N-ACETYL-2-NITRO-P-ANISIDINE;N-(4-METHOXY-2-NITROPHENYL)ACETAMIDE
• CAS NO: 119-81-3
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.19
• EINECS: 204-353-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 119-81-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 117-118°C
• Boiling Point: 349.7°C (rough estimate)
• Flash Point: 216.1°C
• Appearance: /
• Density: 1.3578 (rough estimate)
• Refractive Index: 1.5940 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.24±0.70(Predicted)
• BRN: 2809678
• CAS DataBase Reference: 4-METHOXY-2-NITROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2-NITROACETANILIDE(119-81-3)
• EPA Substance Registry System: 4-METHOXY-2-NITROACETANILIDE(119-81-3)

Safety Data

• Statements: 22
• Safety Statements: 22-36/37
• RIDADR: 2811
• RTECS: AE8310000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 119-81-3(Hazardous Substances Data)

Usage

Description

4-METHOXY-2-NITROACETANILIDE is a chemical compound that serves as a derivative of Methacetin (M258770). It is characterized by the presence of a nitro group and a methoxy group attached to an acetanilide structure. 4-METHOXY-2-NITROACETANILIDE is utilized in various chemical reactions and synthesis processes, particularly in the production of pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Synthesis:
4-METHOXY-2-NITROACETANILIDE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the development of new drugs and therapeutic agents.
Used in the Synthesis of Thiabendazole:
One of the primary applications of 4-METHOXY-2-NITROACETANILIDE is in the synthesis of Thiabendazole (T344150), an active pharmaceutical ingredient. Thiabendazole is a widely used antifungal agent, effective against a variety of fungal infections. The synthesis of this compound involves the use of 4-METHOXY-2-NITROACETANILIDE as a key intermediate, highlighting its importance in the production of this essential medication.
Used in Chemical Research:
4-METHOXY-2-NITROACETANILIDE is also employed in chemical research, where it can be used to study the properties and reactions of various organic compounds. Its unique structure and reactivity make it an interesting subject for research, potentially leading to the discovery of new compounds and applications.

Synthetic route

4-methoxyacetanilide (51-66-1) → 4-methoxy-2-nitroacetanilide (119-81-3) + p-benzoquinone (106-51-4)

Conditions	Yield
With nitric acid; silica gel In dichloromethane for 0.166667h; Product distribution; Ambient temperature;	A 97% B 2%

4-methoxyacetanilide (51-66-1) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 6h; Ionic liquid;	94%
With sulfuric acid; nitric acid at 0 - 5℃;	91%
With nitric acid In dichloromethane at 20℃; for 2h; Heating / reflux;	90%

acetic anhydride (108-24-7) + 4-methoxy-aniline (104-94-9) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
With bismuth (III) nitrate pentahydrate In dichloromethane at 23℃; regioselective reaction;	86%
Stage #1: acetic anhydride; 4-methoxy-aniline With acetic acid In water at 0 - 5℃; Stage #2: With sulfuric acid In water at 60 - 65℃; for 0.166667h; Cooling with ice;

acetic anhydride (108-24-7) + 4-methoxy-2-nitroaniline (96-96-8) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
for 0.00277778h; Green chemistry;	78%
With sulfuric acid Heating;

4-acetylaminomethoxybenzene → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid In water	75%

methanol (67-56-1) + Acetanilid (103-84-4) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
With boron trifluoride diethyl etherate; nitric acid; bis-[(trifluoroacetoxy)iodo]benzene In water at 40℃; for 0.5h;	53%

N-(4-methoxyphenyl)-N'-methylurea (21260-49-1) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
With nitric acid In acetic acid for 0.333333h; Ambient temperature;	30%

acetic anhydride (108-24-7) + 4-methoxy-aniline (104-94-9) + acetic acid (64-19-7) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
at 20℃; anschliessendes Behandeln mit Salpetersaeure in Essigsaeure unterhalb 15grad;

4-methoxy-N-nitrosoacetanilide (14839-81-7) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
In tetrachloromethane at 33℃; for 0.733333h;	0.8 % Chromat.

nitric acid (7697-37-2) + 4-methoxyacetanilide (51-66-1) → 4-methoxy-2-nitroacetanilide (119-81-3)

nitric acid (7697-37-2) + 4-methoxyacetanilide (51-66-1) + acetic acid (64-19-7) → 4-methoxy-2-nitroacetanilide (119-81-3)

4-methoxy-aniline (104-94-9) → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / acetic acid / 2 h / 110 °C 2: 91 percent / nitric acid; sulfuric acid / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid 2: nitric acid; acetic acid View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: nitric acid; acetic anhydride / dichloromethane View Scheme

4-methoxy-aniline (104-94-9) + p-azoanisole → 4-methoxy-2-nitroacetanilide (119-81-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 0.25 h / Heating 2: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min View Scheme

4-methoxy-2-nitroacetanilide (119-81-3) → 4-methoxy-2-nitroaniline (96-96-8)

Conditions	Yield
With potassium hydroxide; sodium hydroxide In water for 0.5h; Heating;	99%
With hydrogenchloride; water In ethanol for 6h; Reflux; Inert atmosphere;	98%
With hydrogenchloride In water for 18h; Reflux;	97.9%

4-methoxy-2-nitroacetanilide (119-81-3) → 2-nitro-4-methoxybenzene diazonium tetrafluoroborate

Conditions	Yield
Stage #1: 4-methoxy-2-nitroacetanilide With boron trifluoride - methanol (1/1) In methanol at 60℃; Inert atmosphere; Reflux; Stage #2: With tert.-butylnitrite In methanol at -15℃; Inert atmosphere;	92%

4-methoxy-2-nitroacetanilide (119-81-3) → 2'-amino-p-acetanisidide (5472-37-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	91%
With hydrogen; palladium on activated charcoal In ethanol under 2585.7 Torr; for 2.5h;	80%
With ethanol; platinum Hydrogenation;

4-methoxy-2-nitroacetanilide (119-81-3) → 6-methoxy-2-methyl-1H-benzo[d]imidazole (4887-81-4)

Conditions	Yield
With iron; acetic acid at 60℃; for 0.5h;	84%

methanol (67-56-1) + 4-methoxy-2-nitroacetanilide (119-81-3) → 4-methoxy-2-nitroaniline (96-96-8)

Conditions	Yield
With potassium hydroxide

4-methoxy-2-nitroacetanilide (119-81-3) → 4-methoxy-2-nitrophenol (1568-70-3)

Conditions	Yield
With sodium hydroxide

4-methoxy-2-nitroacetanilide (119-81-3) → 3,4-dinitroanisole (4280-28-8)

Conditions	Yield
With dihydrogen peroxide; acetic acid

4-methoxy-2-nitroacetanilide (119-81-3) → N-(4-methoxy-2-nitro-phenyl)-thioacetamide (65183-00-8)

Conditions	Yield
With potassium sulphide; phosphorous (V) sulfide; benzene

4-methoxy-2-nitroacetanilide (119-81-3) → acetic acid-(4-methoxy-N-methyl-2-nitro-anilide) (85020-96-8)

Conditions	Yield
With sodium; benzene anschliessendes Behandeln mit Dimethylsulfat;

4-methoxy-2-nitroacetanilide (119-81-3) → acetic acid-(4-methoxy-2,3-dinitro-anilide) (62153-30-4)

Conditions	Yield
With nitric acid
With nitric acid; acetic acid

4-methoxy-2-nitroacetanilide (119-81-3) + acetic acid (64-19-7) → 2'-amino-p-acetanisidide (5472-37-7)

Conditions	Yield
With iron

4-methoxy-2-nitroacetanilide (119-81-3) + 2-(diethylamino)ethyl chloride (100-35-6) → acetic acid-[N-(2-diethylamino-ethyl)-4-methoxy-2-nitro-anilide]

Conditions	Yield
With sodium amide; toluene

4-methoxy-2-nitroacetanilide (119-81-3) + glycerol (56-81-5) → 6-methoxy-8-nitroquinoline (85-81-4)

Conditions	Yield
With sulfuric acid; orthoarsenic acid at 140℃;

4-methoxy-2-nitroacetanilide (119-81-3) + urethane (51-79-6) → 5-methoxy-benzo[1,2,5]oxadiazole (4413-48-3)

Conditions	Yield
With phosphorus pentoxide; xylene

4-methoxy-2-nitroacetanilide (119-81-3) + benzene (71-43-2) → 4-methoxy-2-nitro-1,1'-biphenyl (16098-16-1)

Conditions	Yield
(i) NO, NaOAc, (ii) /BRN= 969212/; Multistep reaction;
(i) N2O4, NaOAc, AcOH, Ac2O, (ii) /BRN= 969212/; Multistep reaction;

4-methoxy-2-nitroacetanilide (119-81-3) → 4-methoxy-N1-ethylbenzene-1,2-diamine (79938-45-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h;	472 mg

4-methoxy-2-nitroacetanilide (119-81-3) + methyl iodide (74-88-4) → acetic acid-(4-methoxy-N-methyl-2-nitro-anilide) (85020-96-8)

Conditions	Yield
With potassium hydroxide In acetone for 0.5h; Heating; Yield given;
In N-methyl-acetamide; ethyl acetate

4-methoxy-2-nitroacetanilide (119-81-3) → 2-bromo-4-methoxy-6-nitrobenzenamine (10172-35-7)

Conditions	Yield
(i) aq. KOH, MeOH, (ii) Br2, AcOH; Multistep reaction;

4-methoxy-2-nitroacetanilide (119-81-3) → 2,3,4,5-tetrabromoanisole (6161-61-1)

Conditions	Yield
With pyridine; bromine; acetic acid

4-methoxy-2-nitroacetanilide (119-81-3) → acetic acid-(4-methoxy-2,6-dinitro-anilide)

Conditions	Yield
With sulfuric acid; nitric acid 1.) 0 deg C, 10 min, 2.) RT, 30 min;

Upstream product

• 108-24-7 acetic anhydride 
• 104-94-9 4-methoxy-aniline 
• 64-19-7 acetic acid 
• 51-66-1 4-methoxyacetanilide 
• 14839-81-7 4-methoxy-N-nitrosoacetanilide 
• 21260-49-1 N-methyl-N'-(p-methoxyphenyl)urea 
• 7697-37-2 nitric acid 
• 96-96-8 4-methoxy-2-nitroaniline 
• 67-56-1 methanol 
• 103-84-4 Acetanilid 

Downstream Products

• 96-96-8 4-methoxy-2-nitroaniline 
• 1568-70-3 4-methoxy-2-nitrophenol 
• 4280-28-8 3,4-dinitroanisole 
• 5472-37-7 2'-amino-p-acetanisidide 
• 65183-00-8 N-(4-methoxy-2-nitro-phenyl)-thioacetamide 
• 85020-96-8 acetic acid-(4-methoxy-N-methyl-2-nitro-anilide) 
• 62153-30-4 acetic acid-(4-methoxy-2,3-dinitro-anilide) 
• 85-81-4 6-methoxy-8-nitroquinoline 
• 16098-16-1 4-methoxy-2-nitro-1,1'-biphenyl 
• 10172-35-7 2-bromo-4-methoxy-6-nitrobenzenamine 
• 6161-61-1 2,3,4,5-tetrabromoanisole 
• 18092-54-1 4-methoxy-2-nitrobenzenesulfonyl chloride 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 

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