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Hydrobromide

Hydrobromide is a class of chemical salts formed by the protonation of an organic base, such as an alkaloid or amine, with hydrobromic acid (HBr), resulting in a bromide anion paired with the protonated base cation.^[1] These salts are typically crystalline solids that exhibit enhanced water solubility compared to the free base, making them valuable in various chemical and pharmaceutical applications.^[1] Hydrobromic acid itself is a strong, colorless acid derived from the dissolution of hydrogen bromide gas in water, serving as the key reagent in their synthesis.^[2] In chemistry, hydrobromide salts are employed as intermediates in organic synthesis, where they facilitate reactions like nucleophilic substitutions or provide stable forms for handling reactive bases; for instance, 3-bromopropylamine hydrobromide is used in the preparation of heterocyclic compounds.^[1] Their formation often involves direct addition of HBr to the base in a solvent, yielding products that are more stable under ambient conditions than the corresponding free bases, which may be prone to oxidation or volatility.^[3] Physicochemically, hydrobromides demonstrate good thermal stability and defined melting points, aiding in purification processes like recrystallization.^[4] In pharmaceuticals, hydrobromide salts are among the common counterions selected to improve drug bioavailability, dissolution rates, and formulation stability for basic therapeutic agents, ranking alongside hydrochlorides and mesylates in usage over the past two decades.^[5] Notable examples include dextromethorphan hydrobromide, a widely used antitussive in over-the-counter cough suppressants, which enhances the drug's solubility for oral administration,^[6] galantamine hydrobromide, an acetylcholinesterase inhibitor for treating Alzheimer's disease,^[1] and scopolamine hydrobromide, an anticholinergic agent for motion sickness and postoperative nausea.^[7] These formulations leverage the bromide ion's mild properties to minimize toxicity while optimizing pharmacokinetic profiles.^[8]

Overview

Definition

Hydrobromide refers to a class of ionic salts formed through the protonation of an organic base, such as amines or alkaloids, by hydrobromic acid (HBr). This reaction yields a protonated base cation paired with a bromide anion, generally represented as [BH]^{+} Br^{-}, where B denotes the organic base.^[1]^[2] For amine-based hydrobromides, the structures follow standard patterns for acid addition salts: primary amines form \ce{RNH3+ Br-}, while secondary amines yield \ce{R2NH2+ Br-}, with R representing alkyl or aryl groups.^[1] These salts are distinct from simple metal bromides, as they specifically arise from HBr interaction with basic nitrogen-containing compounds, often improving the aqueous solubility of the parent base compared to its neutral form.^[9] Representative examples include scopolamine hydrobromide, an alkaloid salt with the formula \ce{C17H21NO4 \cdot HBr}, used in pharmaceutical contexts. Another is ephedrine hydrobromide, derived from the amine alkaloid ephedrine.

Historical Context and Importance

Hydrobromide salts have been synthesized since the 19th century through the reaction of organic bases with hydrobromic acid, paralleling advancements in alkaloid chemistry. This method gained traction as a means to convert poorly soluble free bases into more manageable forms, marking an early advancement in organic salt chemistry that paralleled the broader development of pharmaceutical formulations.^[5] The importance of hydrobromide salts lies in their ability to enhance the aqueous solubility of organic bases compared to their free forms, thereby improving drug bioavailability and enabling effective delivery in sedatives and anesthetics.^[10] This property has been particularly valuable in pharmaceutical development, where salt formation addresses formulation challenges and supports therapeutic efficacy without altering the active moiety's pharmacology.^[5] Key milestones include the introduction of scopolamine hydrobromide in 1921 as one of the earliest pharmacological treatments for motion sickness, leveraging its anticholinergic effects to alleviate nausea and vomiting.^[11] Hydrobromide salts represent a small percentage (less than 3%) of acid-addition salts among FDA-approved pharmaceuticals as of 2022, underscoring their niche yet enduring role in drug design despite the dominance of hydrochlorides.^[12]

Chemical Properties

Structure and Bonding

Hydrobromide salts are ionic compounds formed by the protonation of a base, typically an amine, resulting in a cationic species such as an alkylammonium ion (e.g., R-NH₃⁺) paired with the bromide anion (Br⁻).^[1] This ionic architecture arises from the acid-base reaction where the base accepts a proton from hydrobromic acid, yielding a positively charged nitrogen center electrostatically balanced by the monovalent bromide ion.^[1] In the solid state, the crystal lattice of hydrobromide salts is primarily stabilized by hydrogen bonding interactions between the N-H groups of the protonated cation and the bromide anion, often denoted as N-H⋯Br bonds. These interactions form extended networks, such as dimers or chains, that contribute to the overall structural integrity.^[13] For instance, in NH-pyrazolium hydrobromides, the cations are linked to bromide anions via multiple N-H⋯Br hydrogen bonds, creating dimeric units as confirmed by analysis of the Cambridge Structural Database.^[13] Crystal structures of specific hydrobromide salts illustrate layered ionic packing reinforced by these hydrogen bonds and additional non-covalent interactions. In (S)-amphetamine hydrobromide, [(2S)-1-phenylpropan-2-aminium] bromide, the bromide anion forms three N-H⋯Br hydrogen bonds with surrounding cations, organizing into layers in the bc plane.^[14] This arrangement highlights the role of both ionic and hydrogen bonding in dictating the solid-state architecture of such salts. Compared to analogous hydrochloride salts, hydrobromide salts exhibit weaker ion pairing due to the larger ionic radius of Br⁻ (approximately 1.96 Å) versus Cl⁻ (1.81 Å), which diffuses the electrostatic attraction and can enhance solubility in polar solvents. This difference in anion size influences the lattice energy and intermolecular forces, often resulting in distinct packing motifs and physicochemical properties.^[5]

Physical Characteristics

Hydrobromide salts, which are ionic compounds formed from hydrobromic acid and various bases such as amines, typically appear as white to off-white crystalline solids that exhibit hygroscopic behavior, readily absorbing moisture from the atmosphere.^[15]^[16] These salts demonstrate high solubility in water and polar solvents due to their ionic nature, facilitating dissociation in protic media, while exhibiting lower solubility in non-polar solvents. For instance, scopolamine hydrobromide is soluble in water at approximately 500 g/L at 25°C.^[17]^[18] The melting points of hydrobromide salts vary depending on the associated base but are generally higher than those of the corresponding free bases owing to the stabilizing ionic lattice energy; boiling points are less commonly reported as decomposition often occurs prior to boiling. Ephedrine hydrobromide, for example, melts at 180–185°C.^[19] In infrared (IR) spectroscopy, hydrobromide salts of amines show characteristic broad absorption bands for the N-H stretching vibration of the protonated ammonium group in the range of 2500–3300 cm⁻¹, indicative of hydrogen bonding and protonation.^[20]

Reactivity and Stability

Hydrobromide salts, typically formed from organic bases and hydrobromic acid, exhibit partial dissociation in aqueous solutions into the protonated base cation (BH⁺) and bromide anion (Br⁻). This acid-base equilibrium is governed by the pKa of the conjugate acid BH⁺, which varies depending on the nature of the base; for example, aliphatic amine hydrobromides have a pKa of approximately 10–11, indicating moderate acidity of the protonated amine and influencing the salt's behavior in buffered environments. Thermally, hydrobromide salts demonstrate reasonable stability up to elevated temperatures but decompose above approximately 200°C, releasing hydrogen bromide gas and often yielding dehydrated products such as amides from primary or secondary amine derivatives. This decomposition is analogous to that observed in related hydrohalide salts and proceeds via elimination pathways. Additionally, these salts are sensitive to moisture due to their hygroscopic character, which promotes hydrolysis in humid conditions; adsorbed water creates a localized acidic microenvironment that accelerates degradation, potentially leading to base liberation and bromide ion release.^[21]^[5] In terms of reactivity, the bromide ion serves as a nucleophile in hydrobromide salts, facilitating substitution reactions such as the conversion of alcohols to alkyl bromides under acidic catalysis, where Br⁻ attacks electrophilic centers with reactivity intermediate between chloride and iodide. The salts maintain stability under neutral pH conditions but degrade in strong basic media, as the elevated pH deprotonates BH⁺ to regenerate the free base B, disrupting the ionic lattice and causing precipitation or phase separation. Photostability is generally high for hydrobromide salts, owing to their ionic structure that prevents the photodissociation observed in free HBr, which can form Br₂ and H₂ upon UV exposure; this contrast enhances their suitability for light-exposed applications compared to the parent acid.^[2]

Preparation Methods

Formation from Hydrobromic Acid

Hydrobromide salts are primarily synthesized through the acid-base neutralization reaction between an organic base, such as an amine, and hydrobromic acid (HBr).^[22] This process protonates the base to form the corresponding ammonium cation paired with a bromide anion, typically represented as B + \ce{HBr} \rightarrow \ce{BH+ Br-}, where B denotes the neutral organic base.^[22] For primary amines, the specific equation is \ce{RNH2 + HBr -> RNH3+ Br-}.^[22] In laboratory procedures, the reaction is commonly conducted in protic solvents like ethanol or water at room temperature to ensure solubility and controlled protonation.^[23] A typical method involves dissolving the organic base in the chosen solvent and adding 48% aqueous HBr dropwise with stirring to maintain an exothermic reaction under mild conditions, followed by solvent evaporation under reduced pressure to promote crystallization of the salt.^[15] This approach yields high-purity products, often exceeding 90% for most amine bases, due to the strong acidity of HBr (pKa ≈ -9) driving complete protonation.^[23] For industrial-scale production, especially in pharmaceuticals, gaseous HBr is preferred to minimize residual water and facilitate anhydrous conditions; it is bubbled directly into a solution or suspension of the base in an inert solvent, with the reaction monitored by pH or gas uptake until equivalence is reached.^[24] This method enhances scalability and purity, as seen in processes yielding over 75% with >99.5% purity after isolation.^[25] Purity is further refined by recrystallization, commonly from methanol, which selectively dissolves impurities while allowing the hydrobromide salt to precipitate upon cooling or concentration. The resulting ionic salt features a protonated base cation electrostatically balanced by the bromide anion.^[22]

Alternative Synthetic Routes

Alternative synthetic routes for hydrobromide salts are employed when direct access to hydrobromic acid is limited or impractical, such as in resource-constrained settings or for moisture-sensitive compounds. These methods often involve in situ generation of HBr or non-aqueous techniques to form the salt with organic bases like amines. Unlike the standard neutralization with HBr, these approaches prioritize safety, scalability, and compatibility with sensitive substrates. One common alternative utilizes alkali bromides to generate HBr in situ. Sodium bromide reacts with phosphoric acid to produce HBr gas or solution via the equation $2 \text{NaBr} + \text{H}_3\text{PO}_4 \rightarrow 2 \text{HBr} + \text{Na}_2\text{HPO}_4, avoiding the sulfur dioxide byproduct associated with sulfuric acid methods.^[26] The resulting HBr can then be bubbled into a solution of the organic base or used directly in a reactor to form the hydrobromide salt, offering a cost-effective route for large-scale preparation. This method is particularly useful for pharmaceutical intermediates where pure HBr is unavailable. Halide exchange reactions provide another pathway, particularly for converting existing salts like hydrochlorides to hydrobromides. Treatment of an amine hydrochloride with silver bromide facilitates anion exchange, precipitating silver chloride due to its lower solubility product (Ksp = 1.8 × 10^{-10}) compared to scenarios enabling bromide incorporation, yielding the desired hydrobromide salt in high yield./Descriptive_Chemistry/Elements_Organized_by_Block/2_p-Block_Elements/Group_17:_The_Halogens/1Group_17:_General_Reactions/Testing_for_Halide_Ions) This technique is selective and minimizes side reactions, though it requires careful control to manage silver waste. Indirect formation of hydrobromide salts occurs during certain bromination reactions in organic synthesis. For instance, the addition of HBr to alkenes generates alkyl bromides, and any excess HBr can be captured by an amine base present in the reaction mixture, forming the hydrobromide salt as a byproduct. This is common in processes involving in situ HBr from reagents like N-methylpyrrolidin-2-one hydrotribromide, where the salt forms alongside the brominated product, primarily for specific amine-derived salts in multi-step syntheses.^[27] Solid-state methods offer solvent-free alternatives, ideal for moisture-sensitive compounds. In a gas-phase approach, solid amine bases are exposed to anhydrous HBr gas in a sealed reactor at 0.1–3 atm and -50°C to 40°C for 1–24 hours, resulting in quantitative formation of the hydrobromide salt with >98% purity.^[24] Mechanochemical grinding of the base with a bromide source, such as under vacuum with anhydrous bromide salts, further enables salt formation without liquids, enhancing stability for hygroscopic materials. These techniques reduce environmental impact and improve handling for labile bases. A representative example is the preparation of cabozantinib hydrobromide, a tyrosine kinase inhibitor salt. The free base is slurried with hydrobromic acid (1:1 molar ratio) in acetone or acetic acid, filtered, and dried under vacuum at 40°C, yielding a pure crystalline form with sharp melting point and no solvation, achieving high purity suitable for pharmaceutical use.^[4] This method demonstrates the efficacy of alternative routes in achieving 95% or greater purity while avoiding aqueous conditions.

Applications

In Pharmaceuticals

Hydrobromide salts play a key role in pharmaceutical formulations by enhancing the solubility of basic drugs that are poorly soluble in water, converting them into ionic species that readily dissociate in aqueous media to improve dissolution and bioavailability. This is especially advantageous for oral and injectable dosage forms, where enhanced solubility facilitates better absorption and therapeutic efficacy. For example, scopolamine hydrobromide, an anticholinergic agent, is formulated for oral and injectable use as an antiemetic to prevent motion sickness and postoperative nausea, capitalizing on its superior water solubility compared to the free base.^[7]^[17] Representative hydrobromide salts in therapeutics include homatropine hydrobromide, utilized as a mydriatic and cycloplegic in ophthalmic solutions to dilate pupils and temporarily paralyze accommodation during eye examinations and for treating uveitis.^[28]^[29] In central nervous system applications, citalopram hydrobromide acts as a selective serotonin reuptake inhibitor for treating major depressive disorder, demonstrating how the hydrobromide counterion supports formulation of CNS-active compounds with optimized solubility.^[30]^[31] These salts offer formulation benefits such as improved chemical stability in solid dosage forms like tablets, where the ionic nature reduces degradation risks under humid conditions compared to free bases. Pharmacokinetically, hydrobromide salts enhance gastrointestinal absorption through rapid dissociation, leading to faster onset. Such properties are often achieved via simple neutralization of the base with hydrobromic acid during preparation.^[5]^[10]

In Organic Synthesis and Industry

Hydrobromide salts, particularly those derived from organic bases such as amines, serve as effective brominating agents in organic synthesis by providing a controlled delivery of bromide ions or bromine equivalents for substitution reactions. For instance, 1,8-diazabicyclo[5.4.0]undec-7-ene hydrobromide perbromide acts as a mild and stable reagent for the regioselective bromination of aromatic compounds under ambient conditions, offering advantages over gaseous bromine by minimizing side reactions and improving handling safety.^[32] Similarly, ammonium hydrotribromide salts enable selective α-monobromination of aryl methyl ketones, achieving high yields (up to 95%) with short reaction times and without the need for additional catalysts, making them suitable for preparing intermediates in complex syntheses.^[33] On an industrial scale, hydrobromide intermediates play a key role in manufacturing brominated agrochemicals, such as pesticides, where bromide delivery from these salts supports the formation of active halogenated structures essential for bioactivity. Additionally, they are integral to the production of flame retardants, with brominated compounds derived via bromine chemistry used extensively in plastics and textiles to inhibit combustion through radical scavenging.^[34] To address environmental concerns, hydrobromide salts are often recyclable in industrial processes, minimizing bromide waste through recovery techniques like oxidation of bromide streams to regenerate bromine. In large-scale operations, such as those processing thousands of tons annually, bromide salts from wastewater are extracted and reconverted, achieving recycling rates exceeding 97% and reducing the need for fresh bromine by up to 98%. This closed-loop approach not only lowers costs but also mitigates environmental release of bromide ions.^[35]

Safety and Regulations

Health and Environmental Hazards

Hydrobromide salts exhibit toxicity profiles that vary by the specific compound, with oral LD50 values for certain examples, such as dextromethorphan hydrobromide, reported at 350 mg/kg in rats, indicating potential harm upon ingestion.^[36] These salts may cause mild skin and eye irritation upon direct contact, depending on the specific compound. Unlike hydrobromic acid, they do not typically release HBr to cause severe burns.^[37] Chronic exposure to bromide ions from these salts is associated with bromism, a condition characterized by neurological effects including ataxia, confusion, memory impairment, and hallucinations resulting from impaired neuronal transmission.^[38] Bromide ions released from hydrobromide salts are persistent in aquatic environments, as they do not readily degrade and can remain in water bodies for extended periods. While inorganic bromide shows low bioaccumulation potential in organisms, elevated levels may contribute to ecological risks through indirect pathways, such as formation of toxic brominated disinfection by-products in water treatment processes.^[39] Mishandling leading to HBr release can contribute to acidic atmospheric deposition, akin to acid rain, exacerbating environmental acidification.^[40] Inhalation of dust from hydrobromide salts may cause respiratory tract irritation, including coughing and shortness of breath. Carcinogenicity data for hydrobromide salts and HBr is limited, with no evidence of significant oncogenic potential in available studies.^[41] Bromide exposure should be avoided during pregnancy, as it can interfere with thyroid hormone homeostasis by competing with iodide uptake, potentially leading to neurodevelopmental risks in the fetus.^[42] Under the Globally Harmonized System (GHS), hydrobromic acid and related hydrobromide salts are classified as hazardous, with pictograms for corrosivity and specific target organ toxicity, due to risks of severe skin burns, eye damage, and respiratory irritation.^[43] The Occupational Safety and Health Administration (OSHA) sets a permissible exposure limit (PEL) for HBr vapor at 3 ppm (10 mg/m³) as an 8-hour time-weighted average (TWA) to prevent acute health effects from occupational exposure.^[44]

Handling Protocols

Hydrobromide compounds, including hydrobromic acid solutions and their salts, require careful storage in airtight, cool, and dry containers to prevent moisture absorption that could lead to the evolution of hydrogen bromide gas, particularly for hygroscopic salts where desiccants such as silica gel are recommended to maintain dryness.^[45]^[46] Storage areas should be well-ventilated, locked, and separated from incompatible materials like strong bases or metals to avoid reactions. When handling hydrobromide compounds, appropriate personal protective equipment is essential, including chemical-resistant gloves (such as butyl rubber or nitrile), safety goggles, protective clothing, and respirators with appropriate filters for dust or vapors; operations involving volatile forms should be conducted in a fume hood to minimize exposure risks.^[45]^[46] In the event of a spill, the area should be evacuated and ventilated immediately, followed by neutralization using a mild base like sodium bicarbonate to form less hazardous salts, after which the material is absorbed with inert sorbents and collected for disposal; drains must be protected to prevent environmental release.^[45]^[47] Disposal of hydrobromide waste must comply with local, national, and international regulations, typically involving neutralization if necessary, followed by treatment at an approved hazardous waste facility, such as incineration for organic hydrobromide salts or dilution and neutralization for aqueous solutions.^[45]^[46] For transportation, hydrobromic acid solutions are classified under UN 1788 as a Class 8 corrosive substance, requiring labeling as corrosive and packaging in compatible containers like glass or polyethylene drums; solid hydrobromide salts may fall under UN 1544 for toxic solids if applicable, with all shipments adhering to DOT, IATA, or IMDG standards.^[45]^[46] These protocols help mitigate health hazards from exposure, such as corrosion or irritation.^[48] Note: Hazards for hydrobromide salts vary significantly depending on the organic base; many pharmaceutical salts have relatively low toxicity compared to hydrobromic acid itself.

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