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

Uses

Different sources of media describe the Uses of 119-81-3 differently. You can refer to the following data:
1. Like Methacetin (M258770) derivative, N-(4-Methoxy-2-nitrophenyl)acetaMide can be used in the synthesis of a Thiabendazole
2. Methacetin (M258770) derivative. Used in the synthesis of a Thiabendazole (T344150) metabolite.

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 
• 96-96-8 4-methoxy-2-nitroaniline 
• 67-56-1 methanol 
• 103-84-4 Acetanilid 
• 7697-37-2 nitric acid 
• 21260-49-1 N-methyl-N'-(p-methoxyphenyl)urea 
• 14839-81-7 4-methoxy-N-nitrosoacetanilide 

Downstream Products

• 16169-28-1 4-methoxy-2-nitro-1-propoxy-benzene 
• 16169-29-2 1-butoxy-4-methoxy-2-nitro-benzene 
• 16169-26-9 1-ethoxy-4-methoxy-2-nitro-benzene 
• 102439-33-8 2-ethoxy-5-methoxy-aniline 
• 27238-35-3 7-methoxy-1,2,4-benzotriazin-3-amine 1-oxide 
• 85020-96-8 acetic acid-(4-methoxy-N-methyl-2-nitro-anilide) 
• 85-81-4 6-methoxy-8-nitroquinoline 
• 5472-37-7 2'-amino-p-acetanisidide 
• 96-96-8 4-methoxy-2-nitroaniline 
• 62153-30-4 acetic acid-(4-methoxy-2,3-dinitro-anilide) 
• 65183-00-8 N-(4-methoxy-2-nitro-phenyl)-thioacetamide 
• 4280-28-8 3,4-dinitroanisole 
• 1568-70-3 4-methoxy-2-nitrophenol 
• 1370724-44-9 1-methoxy-3-nitro[4-²H]benzene 

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