8-Bromo-1-naphthoic Acid: Handling & Application Guide

8-Bromo-1-naphthoic acid is a peri-substituted aromatic carboxylic acid serving as a versatile synthetic building block in cross-coupling reactions, coordination chemistry, and medicinal chemistry research.

CAS Number

19576-08-0 (flag: verify against certificate of analysis)

Molecular Formula

C11H7BrO2

Molecular Weight

251.08 g/mol

Key Structural Feature

Bromine and carboxylic acid substituents at peri-positions (C1 and C8) of naphthalene, creating significant steric interaction

SKU

B587653

Recommended Storage

Cool, dry place away from light; consult SDS for specific temperature requirements

Primary Applications

Palladium-catalyzed cross-coupling, ligand synthesis, atropisomeric scaffold construction

Chemical Identity and Structural Characteristics

8-Bromo-1-naphthoic acid (molecular formula C₁₁H₇BrO₂, MW ≈ 251.08 g/mol) belongs to the class of halogenated naphthalene carboxylic acids. Its defining structural feature is the simultaneous presence of a bromine atom at C-8 and a carboxylic acid group at C-1, placing both substituents in the sterically congested peri positions of the naphthalene ring system.

This peri arrangement forces the C–Br bond and the –COOH group into close spatial proximity, resulting in measurable ground-state strain and restricted rotation. Such conformational constraint makes 8-bromo-1-naphthoic acid particularly valuable in the design of atropisomeric molecules and strained scaffolds. The carboxylic acid moiety provides a handle for further functionalization (esterification, amide coupling, decarboxylative reactions), while the aryl bromide is well suited to transition-metal-catalyzed cross-coupling chemistry.

Recommended Handling and Storage

Personal Protective Equipment (PPE): Handle 8-bromo-1-naphthoic acid in a well-ventilated fume hood. Wear appropriate chemical-resistant gloves, safety goggles, and a laboratory coat at all times. Avoid generating fine dust during weighing; use a balance enclosure or a static-dissipating weigh boat.

Storage: Store in a tightly sealed container in a cool, dry location away from direct light and incompatible materials (strong bases, strong oxidizers). Consult the current Safety Data Sheet (SDS) supplied with SKU B587653 for specific temperature and hazard classification details, as these may vary by lot and regional regulation.

Waste Disposal: Dispose of all waste in accordance with applicable local, national, and institutional regulations for halogenated organic compounds. Do not pour down the drain without verifying compliance with local effluent standards.

Solubility and Solution Preparation

As an aromatic carboxylic acid, 8-bromo-1-naphthoic acid is generally expected to show limited solubility in water at neutral pH but improved solubility upon deprotonation in mildly basic aqueous media. It is anticipated to dissolve more readily in common polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), as well as in polar protic solvents such as ethanol and methanol.

For stock solution preparation: weigh the solid under fume-hood conditions, dissolve in the chosen solvent with gentle warming or sonication if necessary, and verify complete dissolution before use. Filter through a 0.2 µm PTFE membrane syringe filter to remove undissolved particulates when solution clarity is critical. Note: specific solubility data for SKU B587653 should be confirmed from the product Certificate of Analysis (CoA) or by in-house testing, as no validated solubility values are provided in the current source material.

Synthetic and Research Applications

Cross-Coupling Chemistry: The aryl C–Br bond in 8-bromo-1-naphthoic acid is reactive toward palladium-catalyzed cross-coupling protocols, including Suzuki–Miyaura, Negishi, Stille, and Sonogashira couplings. This allows rapid diversification of the naphthalene scaffold to introduce aryl, vinyl, alkynyl, or alkyl groups at C-8 while retaining the C-1 carboxylic acid for downstream transformations.

Atropisomer and Conformationally Restricted Scaffold Design: The peri steric interaction between the bromo and carboxyl groups can be exploited to build axially chiral or conformationally locked intermediates relevant to asymmetric synthesis and materials science.

Coordination Chemistry and Ligand Design: The carboxylate anion derived from 8-bromo-1-naphthoic acid can act as a bridging or chelating ligand in metal–organic frameworks (MOFs) and coordination polymers, while the remaining C–Br bond provides a handle for post-synthetic modification.

Medicinal Chemistry: Naphthoic acid derivatives have been investigated as pharmacophore fragments. The combined steric and electronic properties imparted by the peri-bromo group may modulate receptor binding profiles, although specific biological data for this compound are not provided in the source material and should be established experimentally.

Quality, Purity and Ordering Information

Aladdin Scientific supplies 8-bromo-1-naphthoic acid under SKU B587653. Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC or GC), melting point, and NMR characterization data. Researchers are advised to request the CoA at the time of order and verify purity specifications against experimental requirements before use.

For bulk quantities, custom packaging, or additional analytical data, contact Aladdin Scientific technical support or your regional sales representative. All orders are subject to Aladdin's standard terms regarding shipping, storage, and returns—please refer to the relevant policy pages on the Aladdin website for current details.

Frequently asked questions

What solvents are recommended for dissolving 8-Bromo-1-naphthoic acid?

8-Bromo-1-naphthoic acid is expected to dissolve well in polar aprotic solvents such as DMSO and DMF, and in polar protic solvents such as ethanol and methanol. Aqueous solubility is limited at neutral pH but improves under basic conditions. Always confirm solubility in your specific application solvent and consult the CoA for lot-specific data.

Is 8-Bromo-1-naphthoic acid suitable for palladium-catalyzed cross-coupling reactions?

Yes. The aryl C–Br bond in 8-bromo-1-naphthoic acid is a well-established electrophilic partner in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Sonogashira, and Stille protocols. Reaction optimization (catalyst loading, ligand, base, solvent, temperature) should be performed for each specific coupling partner, and the peri-steric environment should be considered as it may reduce coupling rates relative to less hindered aryl bromides.

How should 8-Bromo-1-naphthoic acid (SKU B587653) be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, and dark location, away from strong bases and oxidizing agents. Specific temperature and hazard classification requirements are detailed in the Safety Data Sheet (SDS) provided with each shipment of SKU B587653. Always check the current SDS and CoA for the most accurate and lot-specific storage recommendations.

What makes the peri-substitution pattern of 8-Bromo-1-naphthoic acid chemically significant?

The simultaneous presence of bromine at C-8 and a carboxylic acid at C-1 creates a peri relationship in which both groups are forced into close spatial proximity across the naphthalene ring. This steric crowding introduces ground-state strain, restricts conformational freedom, and can be exploited to build axially chiral scaffolds or to study through-space electronic interactions, making this compound a useful tool in asymmetric synthesis and conformational studies.

References

1. Aladdin Scientific product page, SKU B587653: 8-Bromo-1-naphthoic acid. Internal product descriptor BD13575.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, 5th edition. General reference for aromatic halide cross-coupling and carboxylic acid reactivity.
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press, 2nd edition. Reference for peri-substitution effects in naphthalene systems.

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