ortho-Anisidine 2-Methoxyaniline · CAS 90-04-0

What is ortho-Anisidine?

ortho-Anisidine, also known as 2-methoxyaniline, is an aniline ring carrying a methoxy group at the 2-position relative to the amine, formula C₇H₉NO. It is supplied as a colourless to light orange or yellow liquid, with colour darkening over time as the material oxidises.

Its value as an intermediate comes from the combination of a reactive amine and an electron-donating methoxy group positioned ortho to it, which gives it the diazo-coupling behaviour behind a large family of azo pigments — notably the Pigment Yellow and Pigment Orange series used across printing inks, paints and plastics.

Commercially it is produced by the catalytic hydrogenation of 2-nitroanisole, which is itself obtained by nitrating anisole and separating the ortho-isomer.

Handling follows standard precautions for an aromatic amine — chemical-resistant gloves and eye protection, adequate ventilation, and storage away from incompatible materials such as strong oxidisers, acids, acid chlorides and acid anhydrides. Like most anilines, it darkens with prolonged exposure to air and light.

Why ortho-Anisidine specifically

• A specific methoxy-amine relationship. The ortho (2-) substitution pattern gives the diazo-coupling behaviour that the meta- and para-anisidine isomers do not replicate in the same way.
• Leading azo-pigment diazo component. The standard starting material for the Pigment Yellow/Orange family of diarylide and disazo pigments.
• Agrochemical & pharma building block. A starting material for agrochemical and pharmaceutical intermediate routes needing a 2-methoxyaniline.
• Distinct from meta- and para-anisidine. The reactivity and colour-development behaviour differ enough from the other anisidine isomers that they are not interchangeable in most syntheses.

How ortho-Anisidine is Manufactured

ortho-Anisidine is produced by the catalytic hydrogenation of 2-nitroanisole, which is itself made by nitrating anisole and separating the ortho-isomer from the meta- and para- fractions.

• Nitration. Anisole is nitrated to give a mixture of nitroanisole isomers.
• Separation. The 2-nitroanisole fraction is isolated from the meta- and para- isomers.
• Hydrogenation. 2-Nitroanisole is reduced, typically by catalytic hydrogenation, to ortho-Anisidine.
• Quality release and packing. Assay, colour and isomer purity are confirmed against specification before the batch is packed and released, typically under nitrogen to limit oxidation.

Typical Commercial Specification

Figures below are representative of commercial-grade ortho-Anisidine. Tell us your downstream route and the grade you need, and we will advise on the specification to order against.

Physical & Chemical Properties

Behaviour in the process

ortho-Anisidine's reactivity pattern is what pigment, agrochemical and pharma intermediate producers are buying:

• Diazotisation. The free amine is diazotised and coupled with naphthol and acetoacetanilide-type components to build azo pigments.
• Oxidative sensitivity. Like many anilines, it darkens on prolonged exposure to air and light; store accordingly.
• Chemical attack on plastics/rubber. Can attack some plastics, rubber and coatings; confirm material compatibility for storage and transfer equipment.

ortho-Anisidine and Related Anisidines

Choosing between anisidine isomers, or between an anisidine and a chloroaniline, comes down to the position of the substituent and which functional group the target synthesis needs.

Stated plainly: a pigment route built around the ortho-methoxy diazo pattern needs this specific isomer — the meta- and para-anisidine isomers couple differently and are not drop-in substitutes.

Industries We Supply ortho-Anisidine To

The same anisidine isomer feeds a pigment manufacturer, an agrochemical formulator and a pharmaceutical intermediate producer. What changes is the downstream functionalisation chemistry and the documentation each requires.

Where ortho-Anisidine is Used

In downstream functionalisation

ortho-Anisidine's free amine is carried through diazotisation and coupling chemistry to build the target pigment, while the methoxy group's electron-donating character shapes the shade and stability of the resulting colorant. The ortho-methoxy position gives reactivity distinct from the meta- and para-isomers, which is often exactly why a route is designed around this material specifically.

Quality Control & Testing

Every lot is released against a batch-specific Certificate of Analysis, with isomer purity reported alongside the main assay because meta- and para-anisidine carryover affects downstream pigment shade and reaction selectivity.

• ortho-Anisidine content — by GC assay, the primary grade measure.
• Isomer purity — meta- and para-anisidine carryover, reported because it affects downstream chemistry.
• Colour — reported because oxidation darkens anisidines over time.

Common Process Problems & Likely Causes

Packaging, Storage & Shipping

• Standard packing. Drums or jerricans, typically 25 – 200 kg net, with larger bulk formats on contract supply.
• Oxidation protection. Store under nitrogen where possible and keep containers tightly sealed to limit darkening.
• Temperature control. Store in a cool, dry, well-ventilated area away from direct sun, heat and ignition sources.
• Material compatibility. Avoid contact with strong oxidisers, acids, acid chlorides and acid anhydrides; confirm compatibility of storage and transfer equipment, as ortho-Anisidine can attack some plastics, rubber and coatings.
• Transport classification. Commonly shipped under UN 2431 (Anisidines), Class 6.1, Packing Group III — confirm the correct entry and packing group against your own current SDS before shipping.

Hazards & Safe Handling

ortho-Anisidine is toxic if swallowed, in contact with skin or if inhaled, and is classified as a suspected carcinogen under GHS (IARC Group 2B). Standard precautions for an aromatic amine and good laboratory and plant practice apply throughout handling.

• Skin and eye contact. Chemical-resistant gloves and goggles are standard practice for aromatic amines; rinse thoroughly with water on contact.
• Inhalation. Use adequate ventilation when handling, given the material's toxicity and volatility.
• PPE. Chemical-resistant gloves, safety goggles and, where vapour exposure is a concern, a suitable respirator.
• Carcinogenicity classification. Classified as a suspected human carcinogen; minimise exposure and follow your site's occupational exposure controls for GHS Carcinogen Category substances.

Regulatory & Compliance Notes

ortho-Anisidine is a registered specialty methoxyaniline with a carcinogenicity classification that carries specific regulatory obligations in most major markets. Because obligations differ by territory and use, the notes below are orientation rather than legal advice.

• GHS classification. Classified as toxic if swallowed, in contact with skin or if inhaled, and as a suspected carcinogen (Signal word: Danger); the SDS carries the full hazard statements for your grade.
• REACH and chemical inventories. Registered under EU REACH and listed on major chemical inventories.
• Occupational exposure. Its carcinogenicity classification typically triggers stricter workplace exposure-control and monitoring requirements; confirm the rules that apply in your facility's jurisdiction.
• Dangerous goods transport. Commonly shipped under UN 2431 (Anisidines), Class 6.1, Packing Group III. Confirm the correct entry and packing group with your logistics/EHS team against your current SDS before shipping.
• HS code. Commonly declared under the aromatic ether-amine derivatives heading; confirm the exact tariff line with your customs broker for your jurisdiction.

We Supply ortho-Anisidine Worldwide

Chelora Chemicals is a supplier and export partner, not a single-plant trader. We ship ortho-Anisidine from India and from partner sources to customers across Asia, Europe, the Middle East, Africa, and North and South America, handling the export documentation and freight so the material arrives ready to use.

• Incoterms. EXW, FOB, CIF, CFR and DAP quoted to suit your purchasing terms and freight arrangements.
• Ports. Regular shipments through Nhava Sheva (JNPT) and Mundra, with other ports arranged as routing allows.
• Documentation. Commercial invoice, packing list, certificate of origin, COA and SDS issued as a complete set.
• Flexible volumes. From trial quantities up to repeat bulk shipments on a supply contract.

Buying ortho-Anisidine from Chelora

We are an independent sourcing and supply partner. For this product that means settling three things at enquiry: the purity and isomer-purity grade your application needs, the packing format, and the quantity you are buying.

• Documentation on every lot. Batch-specific COA with assay and isomer breakdown, plus the current SDS.
• Analysis before commitment. Representative analysis shared ahead of a commercial order so your lab can qualify the material.
• Quantities. Trial quantities through to larger bulk shipments on contract supply.
• Inspection. Independent third-party inspection available at loading when the contract requires it.
• Related intermediates. Para Phenylenediamine, Para Nitro Aniline and other dye intermediates alongside this product from one supplier.

How ordering works

• Send the enquiry. Purity, isomer-purity grade, quantity, destination port and the Incoterm you buy on.
• We quote. Price, lead time, packing format and a sample COA, normally within one working day.
• Qualify the supply. For first orders or pigment-grade applications, we share the analysis so your technical team can sign off before you commit.
• Confirm the order. Proforma invoice issued; payment terms agreed against the volume and the relationship.
• Ship and document. Packed, labelled and loaded with the full export document set, and tracked through to arrival.

Related Dye & Pigment Intermediates