Chemical Identity and Structural Features

4-Chloro-N1-methylbenzene-1,2-diamine is an ortho-phenylenediamine derivative bearing a chlorine substituent at the 4-position of the benzene ring and an N-methyl group on one of the two amine nitrogens. Its molecular formula is C₇H₉ClN₂, giving a molecular weight of approximately 156.61 g/mol. The compound contains two distinct amine functionalities: a primary aromatic amine (–NH₂) and a secondary N-methylamine (–NHCH₃), both ortho to each other on the aromatic ring. The electron-withdrawing aryl chloride at the para position relative to the secondary amine modulates the nucleophilicity of both nitrogen centers, making this compound a versatile and selective reagent in multi-step synthesis.

The presence of the chloro substituent also provides a handle for further palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), expanding the utility of this building block in medicinal chemistry programs.

Research Applications

4-Chloro-N1-methylbenzene-1,2-diamine serves as a key intermediate in the construction of nitrogen-rich heterocyclic scaffolds. Its ortho-diamine motif is classically employed in the synthesis of benzimidazoles, quinoxalines, and related fused ring systems that are prominent in medicinal chemistry as kinase inhibitors, antimicrobial agents, and antiparasitic compounds.

In dye chemistry, ortho-phenylenediamine derivatives are important precursors to azo dyes and metal-complex dyes. The N-methyl substitution and the aryl chloride in this compound allow controlled differentiation of the two amine groups, enabling selective mono-acylation, condensation, or cyclization reactions under mild conditions.

In materials science, such diamines are explored as monomers for polyimide and polybenzimidazole synthesis, where the chloro substituent can modulate polymer chain packing and thermal properties. Researchers are advised to confirm specific reaction compatibility through preliminary small-scale trials before scale-up.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): Always handle 4-Chloro-N1-methylbenzene-1,2-diamine in a well-ventilated fume hood. Wear appropriate chemical-resistant gloves (nitrile or neoprene), a laboratory coat, and safety goggles. Aromatic amines as a chemical class carry potential health hazards including skin and mucous membrane irritation; some are suspected carcinogens. Avoid inhalation of dust or vapors.

Storage: Store in a tightly sealed container, protected from light and moisture, at controlled room temperature (typically 15–25 °C) or as specified on the Certificate of Analysis (CoA). Keep away from strong oxidizing agents, strong acids, and acyl chlorides that could react with the amine groups.

Waste Disposal: Dispose of waste containing aromatic amines in accordance with local, national, and institutional regulations for hazardous chemical waste. Do not pour down the drain without proper treatment.

Note: Specific GHS hazard classifications, signal words, and precautionary statements should be confirmed from the current Safety Data Sheet (SDS) provided with SKU C194119 prior to use.

Quality, Purity, and Analytical Verification

When sourcing 4-Chloro-N1-methylbenzene-1,2-diamine for research use, purity is a critical parameter that directly affects reaction yields and reproducibility. Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot of SKU C194119 detailing purity by HPLC or GC, identity confirmation by NMR or MS, and physical characterization data.

Key analytical methods for verification include:

• HPLC or GC: Primary method for purity assessment; typical research-grade material should meet purity specifications stated on the CoA.
• NMR Spectroscopy (¹H and ¹³C): Confirms structural identity; characteristic signals include N-methyl singlet (~2.8 ppm), ArH multiplets, and broad NH/NH₂ signals.
• Mass Spectrometry: Confirms molecular ion consistent with C₇H₉ClN₂ (MW 156.61); characteristic isotope pattern for one chlorine atom (M and M+2 peaks in ~3:1 ratio).
• Melting Point: Physical identity check; specific value should be referenced from the CoA or primary literature.

Researchers should request the lot-specific CoA from Aladdin Scientific and verify that purity meets the requirements of their intended application before use.

Ordering and Procurement Information

4-Chloro-N1-methylbenzene-1,2-diamine is available from Aladdin Scientific under SKU C194119. To place an order or request a quotation, contact your regional Aladdin Scientific sales representative or visit the Aladdin Scientific website. Bulk quantities and custom pack sizes may be available upon request; inquire with the sales team regarding lead times and pricing for larger quantities.

When submitting a purchase order, please reference SKU C194119 and specify the required quantity and desired purity grade. Include any project-specific documentation requirements (e.g., CoA, SDS) in your order request. For regulatory or import compliance questions, Aladdin Scientific customer service can assist with providing necessary documentation.

Reward points, promotional pricing, and institutional account benefits may apply; contact Aladdin Scientific procurement support for current offers applicable to your account.