4-Chloro-3-methylanisole: Handling, Storage & Lab Protocol

4-Chloro-3-methylanisole is a halogenated aryl methyl ether used as a versatile intermediate in organic synthesis, particularly in electrophilic aromatic substitution, cross-coupling reactions, and the preparation of fine chemicals and agrochemical building blocks.

Chemical Name

4-Chloro-3-methylanisole

CAS Number

VerificationNeeded — see review_flags

Molecular Formula

C8H9ClO

Molecular Weight

156.61 g/mol

Appearance

Colorless to pale yellow liquid

Storage Condition

Store in a cool, dry, well-ventilated area away from ignition sources

SKU

C131727

Overview and Chemical Properties

4-Chloro-3-methylanisole (SKU: C131727) is an aromatic compound featuring a methoxy group (–OCH₃), a chloro substituent at the para position, and a methyl group at the meta position relative to the methoxy group. Its molecular formula is C₈H₉ClO with a molecular weight of approximately 156.61 g/mol. The compound belongs to the class of halogenated anisoles, which are valued in synthetic chemistry for their dual functionality: the methoxy group acts as an electron-donating activating group toward electrophilic aromatic substitution, while the aryl–chloride bond serves as a handle for transition-metal-catalyzed cross-coupling reactions such as Suzuki, Negishi, and Buchwald–Hartwig couplings. The compound is expected to be a colorless to pale yellow liquid at room temperature with limited water solubility but good miscibility with common organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran, and toluene.

Safety and Handling

As a halogenated aromatic compound, 4-Chloro-3-methylanisole should be handled with appropriate laboratory precautions. Always consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific before use.

• Personal Protective Equipment (PPE): Wear chemical-resistant gloves (nitrile recommended), safety goggles, and a laboratory coat. Work in a fume hood to minimize inhalation of vapors.
• Ventilation: Ensure adequate local exhaust ventilation. The compound has an aromatic odor and vapor inhalation should be avoided.
• Fire Safety: Keep away from heat, sparks, and open flames. Store in a tightly sealed container in a cool, dry, well-ventilated area.
• Waste Disposal: Dispose of all waste in accordance with local, regional, and national regulations for halogenated organic solvents and compounds.
• First Aid: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention if irritation persists. If inhaled, move to fresh air.

Storage and Stability

Proper storage is essential to maintain the purity and reactivity of 4-Chloro-3-methylanisole over time.

• Temperature: Store at room temperature (15–25 °C) in a cool area, away from direct sunlight and heat sources. Refrigerated storage (2–8 °C) may extend shelf life; verify on current product label.
• Container: Keep in the original tightly closed container under an inert atmosphere (nitrogen or argon) if the product is moisture-sensitive or if the container has been partially used.
• Incompatibilities: Avoid contact with strong oxidizing agents, strong bases, and strong acids. Halogenated aromatic compounds may react with reactive metals.
• Shelf Life: Refer to the expiry date printed on the product label. Inspect for discoloration or precipitation before use.

Typical Laboratory Applications and Protocol

4-Chloro-3-methylanisole is primarily employed as an electrophilic aromatic substitution substrate and as a cross-coupling partner. Below is a general-use protocol framework.

Preparation

1. Retrieve the product (C131727) from storage and allow it to equilibrate to room temperature before opening to prevent condensation.
2. Verify purity by checking the certificate of analysis (CoA) available from Aladdin Scientific for lot-specific data.
3. Weigh the required quantity in a fume hood using a calibrated analytical balance.

Solubilization

1. Dissolve in a suitable anhydrous organic solvent (e.g., THF, DCM, toluene, or DMF) at the desired concentration.
2. For reactions requiring anhydrous conditions, use freshly dried solvents and maintain an inert atmosphere.

Reaction Set-Up (General Cross-Coupling Example)

1. Charge a dry Schlenk flask or round-bottom flask with 4-Chloro-3-methylanisole, the coupling partner (e.g., boronic acid for Suzuki coupling), appropriate palladium catalyst, ligand, and base.
2. Degas the solvent system by three freeze-pump-thaw cycles or by sparging with nitrogen/argon for ≥15 minutes.
3. Heat the reaction mixture to the required temperature (typically 80–110 °C for Pd-catalyzed couplings) under inert atmosphere and monitor by TLC or GC.
4. Upon completion, cool to room temperature, quench, and work up according to standard procedures.

Analytical Verification

1. Confirm product identity by ¹H NMR, ¹³C NMR, GC-MS, or HPLC as appropriate.
2. Compare with literature or CoA reference data.

Quality and Specification Notes

Aladdin Scientific supplies 4-Chloro-3-methylanisole (C131727) as a research-grade reagent. Key specification points include:

• Purity: Refer to the current Certificate of Analysis (CoA) for lot-specific purity data. Research-grade material typically targets ≥97% purity by GC.
• Identification: Product is characterized by GC, NMR, and/or MS to confirm structural identity.
• Lot Traceability: Each lot is assigned a unique batch number; contact Aladdin Scientific technical support for CoA requests.
• Regulatory: This compound is intended for research and development use only. Not for diagnostic, therapeutic, food, or household use.

Frequently asked questions

What solvents are compatible with 4-Chloro-3-methylanisole?

4-Chloro-3-methylanisole is soluble in common organic solvents including dichloromethane, tetrahydrofuran, toluene, ethyl acetate, and DMF. It has very limited solubility in water due to its hydrophobic aromatic structure.

What are the primary synthetic applications of 4-Chloro-3-methylanisole?

This compound is widely used as an intermediate in organic synthesis. The aryl chloride moiety makes it a suitable electrophile for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Kumada couplings), while the electron-donating methoxy group facilitates electrophilic aromatic substitution at activated ring positions. It is also used in the preparation of agrochemical and pharmaceutical building blocks.

How should 4-Chloro-3-methylanisole be stored to maintain its quality?

Store 4-Chloro-3-methylanisole in a tightly sealed container in a cool, dry, well-ventilated area away from heat, light, and ignition sources. After partial use, reseal under an inert atmosphere (nitrogen or argon) to prevent degradation. Always consult the product label and SDS for the most current storage recommendations.

Is a Certificate of Analysis (CoA) available for C131727?

Yes, Aladdin Scientific provides lot-specific Certificates of Analysis for C131727. You can request a CoA by contacting Aladdin Scientific customer service or technical support with your lot number.

What precautions should be taken when using 4-Chloro-3-methylanisole in the lab?

Always work in a properly functioning fume hood. Wear nitrile gloves, safety goggles, and a lab coat. Avoid inhalation of vapors and contact with skin or eyes. Keep away from open flames and oxidizing agents. Refer to the current SDS for comprehensive hazard information and emergency procedures.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for electrophilic aromatic substitution and cross-coupling reactions.)
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007
3. Aladdin Scientific Product Page, C131727: 4-Chloro-3-methylanisole. (Refer to current product listing for updated specifications and CoA.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.