2'-Chloro-6'-fluoroacetophenone: Handling & Lab Use Guide

2'-Chloro-6'-fluoroacetophenone is a difunctionalized aromatic ketone bearing both chloro and fluoro substituents ortho to the acetyl group, making it a versatile electrophilic building block for pharmaceutical intermediate synthesis and fine-chemical research.

Chemical Name

2'-Chloro-6'-fluoroacetophenone

SKU / Product Code

C187411

Molecular Formula

C₈H₆ClFO

Molecular Weight

172.58 g/mol

Functional Class

Halogenated aryl ketone (acetophenone derivative)

Key Substitution Pattern

Ortho-chloro and ortho-fluoro groups flanking the carbonyl-bearing carbon

Chemical Identity and Structure

2'-Chloro-6'-fluoroacetophenone (SKU C187411) is an ortho,ortho-disubstituted acetophenone in which a chlorine atom and a fluorine atom occupy the two positions flanking the methyl carbonyl group on the aromatic ring. Its molecular formula is C₈H₆ClFO and its molecular weight is approximately 172.58 g/mol.

The coplanar arrangement of the carbonyl with the sterically hindered ring creates a molecule with restricted rotation and distinctive electronic properties. The strong electron-withdrawing fluorine atom reduces electron density at the ring, while the chlorine substituent offers a handle for further cross-coupling or nucleophilic aromatic substitution (SNAr) chemistry. The ketone carbonyl itself serves as a reactive site for condensation, reduction, and Grignard-type reactions.

This combination of ortho halogens adjacent to an acetyl group renders the compound particularly valuable as a difunctionalized synthon in multi-step pharmaceutical and agrochemical synthesis routes.

Recommended Storage and Stability

As with most halogenated aryl ketones, 2'-Chloro-6'-fluoroacetophenone should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, away from heat sources, open flames, and incompatible materials such as strong oxidizers, strong bases, and reducing agents.

Typical recommended storage temperature is 2–8 °C or ambient cool storage as specified on the product label and certificate of analysis (CoA). Moisture ingress should be minimized because the compound may be susceptible to slow hydrolysis or oxidation under prolonged humid conditions.

Always confirm specific storage conditions against the current CoA and Safety Data Sheet (SDS) provided with SKU C187411, as lot-specific data supersede general guidelines.

Shelf life: Refer to the expiry date printed on the product label. Routine visual inspection for discoloration or crystalline changes prior to use is recommended.

Safe Handling Procedures

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling 2'-Chloro-6'-fluoroacetophenone, including chemical-resistant gloves (e.g., nitrile), safety goggles or a face shield, and a laboratory coat. If handling powders or volatile fractions, use a NIOSH-approved respirator and conduct all operations in a fume hood.

Skin and eye contact: Halogenated ketones can be irritating to skin, eyes, and mucous membranes. In case of skin contact, wash immediately with copious soap and water. In case of eye contact, flush immediately with water for at least 15 minutes and seek medical attention.

Inhalation and ingestion: Avoid breathing vapors or dust. Do not eat, drink, or smoke while handling the reagent. In case of accidental inhalation, move to fresh air immediately.

Waste disposal: Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic waste. Do not pour down drains.

Consult the SDS for SKU C187411 for complete hazard classification, GHS pictograms, first-aid measures, and regulatory information before beginning work.

Synthetic Applications and Reactivity

2'-Chloro-6'-fluoroacetophenone is primarily employed as an electrophilic building block in organic synthesis. Its reactivity stems from three complementary sites:

• Carbonyl group: Participates in nucleophilic addition reactions (e.g., with organometallic reagents, amines, or hydride reducing agents such as NaBH₄) to give secondary alcohols or imines/enamines that can be elaborated further.
• Ortho-chloro group: Susceptible to palladium-catalyzed cross-coupling reactions (Suzuki, Negishi, Buchwald–Hartwig) under appropriate conditions, enabling C–C and C–N bond formation.
• Ortho-fluoro group: The C–F bond can undergo SNAr displacement with oxygen, nitrogen, or sulfur nucleophiles in the presence of a suitable base, offering a route to diverse heteroatom-substituted products.

Typical use cases include the synthesis of pharmaceutical intermediates targeting kinase inhibitors, anxiolytic agents, and other bioactive scaffolds where a sterically defined ortho-dihalogenated aryl ketone motif is required. The compound may also serve as a precursor for heterocyclic ring formation via intramolecular cyclization sequences.

Reaction conditions should be optimized empirically for each transformation; standard protocols from peer-reviewed literature for analogous haloacetophenone substrates provide a useful starting point.

Quality, Purity, and Documentation

Aladdin Scientific supplies 2'-Chloro-6'-fluoroacetophenone (C187411) with a Certificate of Analysis (CoA) that reports purity, appearance, and lot-specific analytical data. Researchers should download or request the CoA for their specific lot number prior to use to verify that material meets the requirements of their assay or synthesis.

Purity is typically assessed by GC or HPLC. Users requiring additional characterization (e.g., NMR, MS, or elemental analysis) should specify this at the time of order or contact Aladdin Scientific customer support.

If analytical results are outside acceptable limits for a particular application, contact Aladdin Scientific technical support or procurement for guidance on alternative grades or custom specifications.

Keep the original packaging intact until the reagent is required; once opened, reseal immediately under inert gas (argon or nitrogen) if the compound is moisture- or air-sensitive, as indicated in the SDS.

Frequently asked questions

What is the primary use of 2'-Chloro-6'-fluoroacetophenone in research?

It is primarily used as an electrophilic building block in pharmaceutical and fine-chemical synthesis. Its dual ortho-halogen substituents and reactive ketone carbonyl enable C–C, C–N bond-forming reactions and nucleophilic aromatic substitutions, making it valuable for constructing complex bioactive intermediates.

How should 2'-Chloro-6'-fluoroacetophenone (C187411) be stored to maintain stability?

Store in a tightly sealed container in a cool, dry, well-ventilated area, typically at 2–8 °C or as specified on the product label and CoA. Keep away from moisture, strong oxidizers, bases, and heat sources. Always consult the lot-specific CoA and SDS for definitive storage requirements.

Can the ortho-fluoro and ortho-chloro groups be selectively functionalized?

Yes, selectivity can often be achieved due to the different reactivity profiles of C–F and C–Cl bonds. The C–F bond is more electrophilic toward SNAr with hard nucleophiles under mild basic conditions, while the C–Cl bond is better suited to transition-metal-catalyzed cross-coupling reactions. Reaction conditions must be carefully optimized and validated for each specific transformation.

What PPE is recommended when handling this compound?

Nitrile gloves, safety goggles or a face shield, and a laboratory coat are the minimum requirements. When handling powders or in situations with potential vapor exposure, use a fume hood and a NIOSH-approved respirator. Full guidance is provided in the SDS for C187411.

Where can I obtain the Certificate of Analysis (CoA) for my lot of C187411?

CoAs for specific lots of C187411 can be downloaded from the Aladdin Scientific website using your lot number, or requested directly through Aladdin Scientific customer support. Always verify that the lot number on the CoA matches your shipment before use.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. [General reference for haloacetophenone reactivity and SNAr chemistry]
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. [Textbook reference for carbonyl reactivity, cross-coupling, and nucleophilic aromatic substitution]
3. Aladdin Scientific. Certificate of Analysis, 2'-Chloro-6'-fluoroacetophenone, SKU C187411. [Lot-specific analytical data; available from supplier on request]

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