6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine: FAQs

6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine is a halogenated, gem-difluoro-substituted benzodioxole aromatic amine widely used as a versatile building block in medicinal chemistry and pharmaceutical synthesis.

CAS / SKU

Aladdin SKU: A187780

Molecular Formula

C7H4BrF2NO2

Molecular Weight

Approximately 252.01 g/mol (needs verification)

Key Functional Groups

Primary amine (–NH2), gem-difluoro dioxole ring, aryl bromide

Primary Application

Pharmaceutical intermediate and medicinal chemistry building block

Storage Recommendation

Store in a cool, dry, well-ventilated area away from moisture and incompatible materials (needs supplier confirmation)

What Is 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine?

6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine (Aladdin SKU: A187780) is an aromatic amine featuring a benzo[d][1,3]dioxole scaffold in which the methylene bridge of the classic methylenedioxy group has been replaced by a gem-difluoromethylene (CF₂) moiety. A bromine substituent is positioned at the 6-position of the aromatic ring, while a primary amino group (–NH₂) occupies the 5-position.

The combination of these three key features—the electron-withdrawing gem-difluoro group, the halogen handle for cross-coupling, and the free amine for further functionalization—makes this compound a multifunctional intermediate. It is closely related structurally to the naturally occurring methylenedioxy benzene scaffold found in many bioactive natural products and drug molecules, but with the metabolically labile methylene replaced by the more stable CF₂ group.

Key Chemical Properties and Structural Features

gem-Difluoro substitution: Replacing the –OCH₂O– bridge of a methylenedioxy group with –OCF₂O– significantly alters the electronic character of the ring. The two fluorine atoms are strongly electron-withdrawing by induction, reducing electron density on the aromatic ring and modifying the pK_a of the adjacent amine. This substitution also improves metabolic stability relative to the parent methylenedioxy compound, since the CF₂ group is resistant to cytochrome P450-mediated oxidation.

Aryl bromide handle: The C–Br bond at the 6-position is well suited to palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira), enabling efficient diversification of the core scaffold during drug discovery campaigns.

Free primary amine: The –NH₂ group provides a reactive site for acylation, sulfonylation, reductive amination, or condensation reactions, granting further structural diversity.

Note: Exact values for boiling point, melting point, density, and solubility are not provided in the available source material and should be confirmed from the product's Certificate of Analysis (CoA) or Safety Data Sheet (SDS).

Handling, Safety, and Storage

As an aromatic amine, 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine should be handled with appropriate caution. General guidelines for this compound class include:

• Personal protective equipment (PPE): Wear nitrile gloves, a lab coat, and safety glasses. Work in a fume hood when weighing or dissolving the compound.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area. Protect from moisture, light, and heat. Refer to the product SDS for specific hazard classifications and storage temperature requirements.
• Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic compounds.
• Incompatibilities: Aromatic amines may react with strong oxidizing agents and strong acids; avoid contact with such materials.

Always consult the Aladdin Scientific SDS for A187780 for compound-specific hazard data before use.

Applications in Medicinal Chemistry and Drug Discovery

The gem-difluoromethylenedioxy (–OCF₂O–) motif has attracted considerable interest in medicinal chemistry as a bioisostere of the methylenedioxy (–OCH₂O–) group. Key advantages include improved metabolic stability and altered lipophilicity (logP) relative to the unmodified parent scaffold.

Typical uses of 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine (A187780) and closely related analogs in research include:

• Synthesis of fluorinated pharmaceutical candidates via palladium-catalyzed C–C or C–N bond-forming reactions at the aryl bromide position.
• Construction of amide, urea, or sulfonamide libraries through derivatization of the primary amine.
• Incorporation into screening collections for target-based or phenotypic drug discovery programs.

Specific published syntheses or biological activity data for this exact compound are not available in the current source material; researchers should conduct a primary literature search (e.g., SciFinder, Reaxys) for application-specific references.

Ordering and Product Information

6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine is available from Aladdin Scientific under SKU A187780. To place an order or request additional product information:

• Visit the Aladdin Scientific website and search by SKU A187780 or by the IUPAC name.
• Contact Aladdin Scientific customer service for bulk pricing, custom pack sizes, or Certificate of Analysis requests.
• For purity specifications, lot-specific analytical data, and SDS documents, use the document request function on the product page or contact your regional Aladdin representative.

Standard packaging, available quantities, and current pricing are subject to change; please confirm with Aladdin Scientific at the time of ordering.

Frequently asked questions

What is the molecular formula and molecular weight of 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine?

The molecular formula of 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine is C7H4BrF2NO2, with an approximate molecular weight of 252.01 g/mol. Please verify the exact value against the product's Certificate of Analysis (CoA) available from Aladdin Scientific (SKU: A187780).

Why is the gem-difluoro (–OCF2O–) group important in this compound?

The –OCF2O– group serves as a metabolically stable bioisostere of the methylenedioxy (–OCH2O–) group commonly found in natural products and drug molecules. Because the CF2 unit resists oxidative metabolism by cytochrome P450 enzymes, incorporating this motif can improve the in vivo stability of drug candidates while maintaining or modulating the desired pharmacological profile. It also electronically modifies the aromatic ring and alters the compound's lipophilicity relative to the methylene analog.

What cross-coupling reactions can be performed using the aryl bromide in A187780?

The aryl C–Br bond in 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine is reactive under standard palladium-catalyzed cross-coupling conditions. Commonly applicable reactions include Suzuki–Miyaura (with boronic acids/esters), Buchwald–Hartwig amination (C–N bond formation), Sonogashira coupling (with terminal alkynes), and Negishi or Kumada couplings with organometallic nucleophiles. Reaction optimization should be performed to account for the electron-withdrawing effect of the –OCF2O– group on reactivity.

How should 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine be stored to maintain stability?

General best practice for aromatic amine building blocks is to store them in a tightly sealed container under cool, dry, and well-ventilated conditions, protected from light and moisture. Specific storage temperature requirements for A187780 should be confirmed from the Aladdin Scientific product page or the compound's Safety Data Sheet (SDS), as these details were not included in the available source material.

How do I order 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine from Aladdin Scientific?

You can order this compound directly from Aladdin Scientific using SKU A187780. Search for the SKU or the IUPAC name on the Aladdin Scientific website to view available pack sizes, pricing, and stock status. For bulk orders, custom quantities, or Certificate of Analysis requests, please contact Aladdin Scientific customer service directly.

References

1. Fluorine in Medicinal Chemistry: general textbook principles on CF2 bioisosterism and metabolic stability of difluoromethylenedioxy compounds.
2. Aladdin Scientific product page for A187780: 6-Bromo-2,2-difluorobenzo[d][1,3]dioxol-5-amine.
3. Palladium-catalyzed cross-coupling reactions of aryl halides: general textbook reference (e.g., Metal-Catalyzed Cross-Coupling Reactions, de Meijere and Diederich, eds.).

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