{"id":3454,"date":"2024-07-19T06:12:52","date_gmt":"2024-07-19T06:12:52","guid":{"rendered":"https:\/\/pharm.sinocurechem.com\/?p=3454"},"modified":"2024-07-19T06:12:52","modified_gmt":"2024-07-19T06:12:52","slug":"o-anisidine-2-methoxyaniline-chemical-properties-synthesis-applications-and-safety-considerations","status":"publish","type":"post","link":"https:\/\/longchangextracts.com\/da\/o-anisidine-2-methoxyaniline-chemical-properties-synthesis-applications-and-safety-considerations\/","title":{"rendered":"o-Anisidin (2-Methoxyanilin): Kemiske egenskaber, syntese, anvendelser og sikkerhedsovervejelser"},"content":{"rendered":"

o-Anisidine (2-Methoxyaniline): Chemical Properties, Synthesis, Applications, and Safety Considerations<\/span><\/i><\/b><\/i><\/b><\/p>\n

o-Anisidine CAS 90-04-0<\/span><\/i><\/b><\/i><\/b><\/p>\n

o-Anisidine, also known as 2-methoxyaniline, is an aromatic amine with the chemical formula C7H9NO. It is a colorless to yellowish liquid with a characteristic odor, used primarily as an intermediate in the synthesis of various dyes, pigments, and pharmaceuticals.<\/span><\/p>\n

1.\u00a0<\/span>Chemical Properties<\/span><\/b><\/b><\/p>\n

IUPAC Name: 2-Methoxyaniline<\/span><\/p>\n

CAS Number: 90-04-0<\/span><\/p>\n

Molecular Formula: C7H9NO<\/span><\/p>\n

Molecular Weight: 123.15 g\/mol<\/span><\/p>\n

Structure: The chemical structure consists of a benzene ring substituted with a methoxy group (-OCH3) at the ortho position and an amino group (-NH2) at the para position.<\/span><\/p>\n

Appearance: Colorless to yellowish liquid<\/span><\/p>\n

Boiling Point: 218-219\u00b0C<\/span><\/p>\n

Melting Point: -2\u00b0C<\/span><\/p>\n

Density: 1.088 g\/cm\u00b3 at 20\u00b0C<\/span><\/p>\n

Solubility: Soluble in organic solvents like ethanol, ether, and chloroform; slightly soluble in water.<\/span><\/p>\n

2.\u00a0<\/span>Synthesis<\/span><\/b><\/b><\/p>\n

1)\u00a0<\/span>Reduction of o-Nitroanisole<\/span><\/b><\/b><\/p>\n

One of the primary methods for synthesizing o-anisidine is the reduction of o-nitroanisole (2-nitroanisole). This process can be carried out using various reducing agents, each offering distinct advantages depending on the scale and specific requirements of the synthesis.<\/span><\/p>\n

Catalytic Hydrogenation: This method involves the reduction of o-nitroanisole using hydrogen gas in the presence of a suitable catalyst. Common catalysts include palladium on carbon (Pd\/C), platinum (Pt), or Raney nickel.<\/span><\/p>\n

Reaction Conditions: The reaction is typically performed in an appropriate solvent such as ethanol, methanol, or acetic acid. The mixture is subjected to hydrogen gas under controlled pressure and temperature.<\/span><\/p>\n

Advantages: Catalytic hydrogenation provides a high yield of o-anisidine with minimal by-products. The process is efficient and can be scaled up for industrial production.<\/span><\/p>\n

Mechanism: The nitro group (-NO2) in o-nitroanisole is reduced to an amino group (-NH2) through successive stages involving the formation of intermediate nitroso and hydroxylamine species.<\/span><\/p>\n

Chemical Reduction: Alternatively, o-nitroanisole can be reduced using chemical reducing agents such as iron filings in the presence of hydrochloric acid (Bechamp reduction), zinc dust, or sodium sulfide.<\/span><\/p>\n

Bechamp Reduction: Iron filings and hydrochloric acid reduce o-nitroanisole to o-anisidine. This method is historically significant and is still used in certain applications.<\/span><\/p>\n

Advantages: Chemical reduction methods are cost-effective and suitable for large-scale synthesis, especially in environments where catalytic hydrogenation infrastructure is not available.<\/span><\/p>\n

2)\u00a0<\/span>Methylation of Aniline<\/span><\/b><\/b><\/p>\n

Another approach to synthesizing o-anisidine involves the methylation of aniline (phenylamine) followed by selective demethylation.<\/span><\/p>\n

Methylation with Dimethyl Sulfate: Aniline can be methylated using dimethyl sulfate to form N-methylaniline and subsequently N,N-dimethylaniline.<\/span><\/p>\n

Reaction Conditions: Aniline is reacted with dimethyl sulfate in the presence of a base such as sodium hydroxide or potassium carbonate. The reaction is typically conducted in an organic solvent like acetone or dimethylformamide (DMF).<\/span><\/p>\n

Demethylation: The resulting N,N-dimethylaniline is subjected to selective demethylation to yield o-anisidine. This step can be achieved using reagents like hydrobromic acid (HBr) or boron tribromide (BBr3).<\/span><\/p>\n

3)\u00a0<\/span>Direct Etherification<\/span><\/b><\/b><\/p>\n

A less common but viable method for synthesizing o-anisidine involves the direct etherification of aniline with methanol or dimethyl ether under acidic conditions.<\/span><\/p>\n

Etherification Process: Aniline is reacted with methanol in the presence of an acid catalyst such as sulfuric acid or hydrochloric acid.<\/span><\/p>\n

Reaction Conditions: The mixture is heated under reflux to promote the formation of the methoxy group (-OCH3) at the ortho position relative to the amino group (-NH2).<\/span><\/p>\n

Advantages: This method provides a straightforward route to o-anisidine, though it may require stringent control of reaction conditions to minimize side reactions and achieve high selectivity.<\/span><\/p>\n

4)\u00a0<\/span>Nitration and Reduction Sequence<\/span><\/b><\/b><\/p>\n

A more elaborate synthetic route involves the nitration of anisole followed by selective reduction.<\/span><\/p>\n

Nitration of Anisole: Anisole (methoxybenzene) is nitrated using a mixture of concentrated nitric acid and sulfuric acid to yield a mixture of nitroanisole isomers.<\/span><\/p>\n

Reaction Conditions: The nitration is conducted at controlled temperatures to favor the formation of the ortho-nitroanisole isomer.<\/span><\/p>\n

Separation: The isomers are separated using techniques such as fractional distillation or chromatography.<\/span><\/p>\n

Reduction to o-Anisidine: The ortho-nitroanisole is then selectively reduced to o-anisidine using catalytic hydrogenation or chemical reduction methods, as described earlier.<\/span><\/p>\n

3.\u00a0<\/span>Applications<\/span><\/b><\/b><\/p>\n

Dye and Pigment Industry:<\/span><\/b><\/b><\/p>\n

o-Anisidine is a crucial intermediate in the synthesis of various dyes and pigments, particularly:<\/span><\/p>\n

a) Azo dyes: Used extensively in textile, leather, and paper industries<\/span><\/p>\n

b) Triphenylmethane dyes: Employed in inks, paints, and biological stains<\/span><\/p>\n

c) Indigo dyes: Used in denim and other textile applications<\/span><\/p>\n

d) Quinoline dyes: Applied in various industrial and consumer products<\/span><\/p>\n

Pharmaceutical Industry:<\/span><\/b><\/b><\/p>\n

o-Anisidine serves as a starting material or intermediate in the synthesis of:<\/span><\/p>\n

a) Analgesics and anti-inflammatory drugs<\/span><\/p>\n

b) Antihypertensive agents<\/span><\/p>\n

c) Antihistamines<\/span><\/p>\n

d) Local anesthetics<\/span><\/p>\n

e) Antimicrobial compounds<\/span><\/p>\n

Agrochemical Sector:<\/span><\/b><\/b><\/p>\n

The compound is utilized in the production of:<\/span><\/p>\n

a) Herbicides: As a precursor in triazine-based herbicides<\/span><\/p>\n

b) Insecticides: Particularly in the synthesis of some organophosphate compounds<\/span><\/p>\n

c) Fungicides: As an intermediate in certain azole-based fungicides<\/span><\/p>\n

Flavor and Fragrance Industry:<\/span><\/b><\/b><\/p>\n

o-Anisidine is a key precursor in the synthesis of:<\/span><\/p>\n

a) Vanillin: The primary component of vanilla flavor<\/span><\/p>\n

b) Ethylvanillin: A more potent synthetic vanilla flavoring<\/span><\/p>\n

c) Guaiacol: Used in the production of various flavors and fragrances<\/span><\/p>\n

Polymer and Rubber Industry:<\/span><\/b><\/b><\/p>\n

The compound finds applications in:<\/span><\/p>\n

a) Antioxidants for rubber and plastics<\/span><\/p>\n

b) Curing agents for epoxy resins<\/span><\/p>\n

c) Stabilizers in polymer production<\/span><\/p>\n

Corrosion Inhibitors:<\/span><\/b><\/b><\/p>\n

o-Anisidine derivatives are used as corrosion inhibitors in:<\/span><\/p>\n

a) Industrial cooling systems<\/span><\/p>\n

b) Oil and gas pipelines<\/span><\/p>\n

c) Metal processing industries<\/span><\/p>\n

Research and Analytical Chemistry:<\/span><\/b><\/b><\/p>\n

o-Anisidine serves as:<\/span><\/p>\n

a) A reagent in various organic syntheses<\/span><\/p>\n

b) A standard in analytical chemistry for method development and validation<\/span><\/p>\n

Specialty Chemicals:<\/span><\/b><\/b><\/p>\n

The compound is utilized in the production of:<\/span><\/p>\n

a) Optical brighteners for textiles and paper<\/span><\/p>\n

b) UV absorbers for plastics and cosmetics<\/span><\/p>\n

c) Antioxidants for fuels and lubricants<\/span><\/p>\n

4.\u00a0<\/span>Safety<\/span><\/b><\/b><\/p>\n

o-Anisidine is classified as a hazardous substance due to its toxicological properties. It can be absorbed through the skin, inhalation, or ingestion, causing various health effects.<\/span><\/p>\n

Health Hazards: Exposure to o-anisidine can cause irritation to the skin, eyes, and respiratory tract. Prolonged exposure may lead to methemoglobinemia, a condition where hemoglobin is unable to effectively release oxygen to body tissues. It is also considered a potential carcinogen.<\/span><\/p>\n

5.\u00a0<\/span>Handling and Storage<\/span><\/b><\/b><\/p>\n

Personal Protective Equipment (PPE): When handling o-anisidine, appropriate PPE such as gloves, goggles, and lab coats should be worn to minimize exposure.<\/span><\/p>\n

Storage: It should be stored in a cool, well-ventilated area away from sources of ignition. Containers should be tightly sealed to prevent leakage and contamination.<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"

o-Anisidine (2-Methoxyaniline): Chemical Properties, Synthesis, Applications, and Safety Considerations o-Anisidine CAS 90-04-0 o-Anisidine, also known as 2-methoxyaniline, is an aromatic amine with the chemical formula C7H9NO. It is a colorless to yellowish liquid with a characteristic odor, used primarily as an intermediate in the synthesis of various dyes, pigments, and pharmaceuticals. 1.\u00a0Chemical Properties IUPAC Name: […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[20],"tags":[],"yoast_head":"\no-Anisidine (2-Methoxyaniline): Chemical Properties, Synthesis, Applications, and Safety Considerations - China Chemical Manufacturer<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/longchangextracts.com\/da\/o-anisidin-2-methoxyanilin-kemiske-egenskaber-syntese-anvendelser-og-sikkerhedsovervejelser\/\" \/>\n<meta property=\"og:locale\" content=\"da_DK\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"o-Anisidine (2-Methoxyaniline): Chemical Properties, Synthesis, Applications, and Safety Considerations - China Chemical Manufacturer\" \/>\n<meta property=\"og:description\" content=\"o-Anisidine (2-Methoxyaniline): Chemical Properties, Synthesis, Applications, and Safety Considerations o-Anisidine CAS 90-04-0 o-Anisidine, also known as 2-methoxyaniline, is an aromatic amine with the chemical formula C7H9NO. 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