6375-47-9

Basic information

• Product Name: 3'-Amino-4'-methoxyacetanilide
• Synonyms: 2-AMINO-4-ACETAMIDOANISOLE;2-AMINO-4-ACETYLAMINOANISOLE;3-AMINO-4-METHOXY ACETANILIDE;3'-AMINO-4'-METHOXYACETANILIDE;3-AMINO-4-METHOXYACETANILINE;3'-AMINO-4'-METHOXYACETOANILIDE;4-ACETOAMINO-2-AMINO METHOXYBENZENE;4-ACETAMINO-2-AMINOANISOLE
• CAS NO: 6375-47-9
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.2
• EINECS: 228-938-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 6375-47-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 109°C
• Boiling Point: 313.03°C (rough estimate)
• Flash Point: 199.2 °C
• Appearance: /
• Density: 1.1819 (rough estimate)
• Vapor Pressure: 2.46E-15mmHg at 25°C
• Refractive Index: 1.5373 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 14.23±0.70(Predicted)
• CAS DataBase Reference: 3'-Amino-4'-methoxyacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Amino-4'-methoxyacetanilide(6375-47-9)
• EPA Substance Registry System: 3'-Amino-4'-methoxyacetanilide(6375-47-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 6375-47-9(Hazardous Substances Data)

Usage

General Description

3'-Amino-4'-methoxyacetanilide, also known as acetaminophen, is a widely used over-the-counter pain reliever and fever reducer. It is a synthetic compound with analgesic and antipyretic properties, often used to alleviate mild to moderate physical discomfort associated with conditions such as headaches, muscle aches, arthritis, and colds. Acetaminophen works by inhibiting the production of prostaglandins, which are chemicals in the body that promote pain and fever. It is considered a safe and effective medication when taken in appropriate doses, but excessive consumption can lead to liver damage and other serious complications. Therefore, it is important to use this chemical responsibly and as directed by a healthcare professional.

InChI:InChI=1/C22H19NO5/c1-27-19-11-13(7-9-17(19)24)22(14-8-10-18(25)20(12-14)28-2)15-5-3-4-6-16(15)23-21(22)26/h3-12,24-25H,1-2H3,(H,23,26)

Synthetic route

2-nitro-4-acetylamino-anisole (50651-39-3) + formic acid hydrazide (624-84-0) → 3-amino-4-methoxyacetanilide (6375-47-9)

Conditions	Yield
With palladium on activated charcoal In methanol at 20℃;	99.5%

2,4-Diaminoanisole (615-05-4) + acetic anhydride (108-24-7) → 3-amino-4-methoxyacetanilide (6375-47-9)

Conditions	Yield
With sodium carbonate In methanol at 5℃; for 0.00416667h; Temperature; Concentration; Reagent/catalyst; Time;	99%
With sodium carbonate In methanol at 5℃; Reagent/catalyst; Temperature;	98.6%
In methanol at 0 - 5℃; for 1.16667h; Solvent; Large scale;	98.5%

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 50℃; under 4500.45 Torr; for 0.416667h;	98.1%
With hydrogen In methanol at 60℃; under 11251.1 Torr;	96.52%
With hydrogen at 80℃; under 7500.75 Torr; Large scale;	96.52%

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
Multi-step reaction with 3 steps 1: PEG4000 / 60 °C / Large scale 2: hydrogen / methanol / 60 °C / 4500.45 Torr / pH 9 3: sodium carbonate / methanol / 5 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / 3 h / 60 °C 2: PdCu/graphene double-metal catalyst / 0.58 h / 60 °C / 7500.75 Torr 3: ammonium bicarbonate / methanol / -5 - 5 °C 4: palladium on activated charcoal; hydrogen / methanol / 0.42 h / 50 °C / 4500.45 Torr View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 35 - 65 °C 2: sodium disulfide / water / 80 °C 3: acetic acid; triethylamine / 2.5 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: PEG2000 / methanol / 60 °C 2: palladium on activated charcoal; formic acid hydrazide / methanol 3: magnesium oxide / methanol / -5 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: PEG4000 (polyethyleneglycol 4000) / 60 °C 2: hydrogen / methanol / 40 °C / 30003 Torr / Autoclave 3: sodium carbonate / methanol / -5 - 5 °C View Scheme

→ 3-amino-4-methoxyacetanilide

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon / methanol / 30 - 40 °C / 375.04 - 1500.15 Torr / Inert atmosphere 2: sulfuric acid; nitric acid / 3 h 3: palladium 10% on activated carbon / methanol / 30 - 40 °C / 375.04 - 1500.15 Torr / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: hydrogen / methanol / 80 °C / 9000.9 Torr / Large scale 2: 8 h / 190 °C 3: nitric acid; sulfuric acid / water / 12 h / 0 - 5 °C 4: hydrogen / methanol / 60 °C / 11251.1 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogen; / methanol / 100 °C / 15001.5 Torr / Large scale 2: 200 °C / Large scale 3: sulfuric acid; nitric acid / 5 °C / Large scale 4: hydrogen; / 80 °C / 7500.75 Torr / Large scale View Scheme

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 50651-39-3 2-nitro-4-acetylamino-anisole 
• 624-84-0 formic acid hydrazide 
• 119-27-7 2,4-dinitroanisole 
• 104-94-9 4-methoxy-aniline 
• 577-72-0 4-methoxy-3-nitroaniline 
• 100-00-5 4-chlorobenzonitrile 
• 100-17-4 para-methoxynitrobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 615-05-4 2,4-Diaminoanisole 
• 108-24-7 acetic anhydride 

Downstream Products

• 24530-67-4 N-{3-[bis(2-hydroxyethyl)amino]-4-methoxyphenyl}acetamide 
• 23128-51-0 3-N,N-bis-β-acetoxyethylamino-4-methoxyacetanilide 
• 51868-45-2 3-(N,N-diprop-2-enamino)-4-methoxyacetanilide 
• 52868-49-2 C₁₄H₂₀N₂O₄ 

Relevant articles and documents

Hydrogenation of 3-nitro-4-methoxy-acetylaniline with H2 to 3-amino-4-methoxy-acetylaniline catalyzed by bimetallic copper/nickel nanoparticles

Monometallic Cu, monometallic Ni, and bimetallic CuxNiy nanoparticles were prepared by a wet chemical reduction method. A Cu-Ni alloy phase was formed in the bimetallic CuxNiy nanoparticles. The bimetallic CuxNiy nanoparticles exhibited higher catalytic activity for the hydrogenation of 3-nitro-4-methoxy-acetylaniline (NMA) to 3-amino-4-methoxy-acetylaniline (AMA) with H2 than the sole Ni nanoparticles, which was ascribed to the effect of the Cu-Ni alloy phase. When the reaction was catalyzed over the bimetallic Cu0.7Ni0.3 catalyst at 140 °C for 2 h, the AMA selectivity was 99.4% when the NMA conversion was 95.7%. The reaction activation energy for NMA hydrogenation was 19.74 kJ mol-1.

Synthesis method for disperse dye intermediate

The invention discloses a synthesis method for a disperse dye intermediate. The synthesis method comprises the following steps: preparing 2,4-diaminophenol through reduction reaction of 2,4-dinitrophenol and hydrogen gas; enabling 2,4-diaminophenol and iodomethane to generate etherification reaction under action of a catalyst tributyl methyl ammonium carbonate to prepare 2,4-diaminoanisole; and enabling 2,4-diaminoanisole and acetic anhydride to generate acylation reaction to prepare a target product 3-amino-4-methoxya-cetanilide. Compared with a 2,4-diaminoanisole hydrogenation reduction process, the 2,4-dinitrophenol hydrogenation reduction process is adopted, so that the conversation rate is high and the side reactions are fewer.

A 2 - amino - 4 - acetyl amino methyl ether synthesis method (by machine translation)

The invention discloses a 2 - amino - 4 - acetyl amino methyl ether synthesis method. The synthetic method comprises the following steps: (1) in the presence of a catalyst A, to nitroanisole with hydrogen by a catalytic hydrogenation reduction reaction to obtain the amino anisole; (2) P a the fuel to the acetylation reaction acetyl amino anisole; (3) to the acetaminophen a fuel for nitration reaction to obtain the 2 - nitro - 4 - acetamido anisole; (4) in the presence of a catalyst B, 2 - nitro - 4 - acetyl amino methyl ether with hydrogen by secondary catalytic hydrogenation reduction reaction. This invention adopts the first acylation, re-nitration, reduction method for synthesis of 2 - amino - 4 - acetyl amino methyl ether, avoids the traditional directional acylate raw material is easy to oxidation in the process, a plurality of side reaction, the product is hard to separate, the problem of low purity, the method of the invention the synthetic product purity can be up to 99.5% -99.8%. (by machine translation)