This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No biological assay or immunoassay applications are provided for this product. As a synthetic reagent, procedures depend on the chosen transformation.
Item-specific tested applications and dilutions: Not specified for this item; refer to CoA/Spec Sheet.
General laboratory use (examples)
Amidation (EDC/DIPEA) protocol: Dissolve acid and amine in dry DMF, cool to 0–5 C, add EDC·HCl and catalytic DMAP, warm to RT, monitor by TLC/LC–MS, then quench and extract.
Suzuki coupling protocol: Combine aryl bromide, boronic acid, Pd catalyst, base, and 2-MeTHF/H2O; heat at 80 C under N2, monitor by HPLC, work up with aqueous NH4Cl and extract.
Always validate on small scale and consult peer-reviewed procedures for closest analogs.
Biological Roles
This product is a small synthetic arylpropionic acid intended for laboratory research and synthesis. No biological roles are assigned in the Product Data.
Item-specific biological information: Not specified for this item; refer to CoA/Spec Sheet.
General context (no medical claims): Arylpropionic acids occur in many research libraries due to their tunable acidity (pKa ~4–5) and capacity to form amide/ester linkages. The presence of aryl bromide/fluoride can modulate lipophilicity and metabolic stability in probe molecules, and the acid function can enhance aqueous solubility when ionized. Any biological evaluation should be conducted under appropriate institutional approvals for research use only.
Buffer Applications
This compound is not a conventional buffering agent and is not typically used to prepare biochemical buffers.
Buffer use: Not applicable. The carboxylic acid can form salts that are water-soluble at basic pH, which may aid handling or extraction, but defined buffering capacity and pKa spacing for classical buffers (e.g., phosphate, Tris, HEPES) are not relevant here.
Recommendation: Use standard buffers for pH control; reserve this compound for synthetic transformations and building-block applications.
Green Alternatives
Greener practices can be adopted without compromising performance for most transformations on this substrate.
Solvent selection (literature guidance)
Replace DMF/NMP with greener polar aprotics such as Cyrene, dimethyl carbonate (DMC), propylene carbonate (PC), or 2-MeTHF/CPME where compatible with reagents and bases.
For Suzuki couplings, aqueous ethanol, 2-MeTHF, or CPME often substitute for dioxane/THF/toluene with appropriate bases (K2CO3/K3PO4) and ligands.
Coupling reagents
Consider EDC·HCl with catalytic DMAP in EtOAc or Me-THF as a lower-toxicity alternative to HATU/HBTU (which generate PF6–/OAt waste). Enzymatic esterifications (lipase-catalyzed) in green solvents may be viable for ester formation.
Energy and workup
Employ microwave or flow conditions to shorten reaction times and reduce solvent volumes; use aqueous bicarbonate/acid toggling to exploit acid/base switchable solubility and minimize organic solvent usage.
Greener shifts: 2-MeTHF/CPME/Cyrene; EtOAc/MeOH/water co-solvent systems; EDC or CDI for activation; use of solid-supported scavengers to reduce washes.
Trade-offs: Greener solvents may alter solubility and reaction rates; ligand/base optimization is often needed. Reagent greenness must be balanced against step count and overall E-factor.
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided in the Product Data.
Item-specific pharma/formulation information: Not specified for this item; refer to CoA/Spec Sheet.
General research/manufacturing context (no therapeutic claims)
May serve as an intermediate for the preparation of amide/ester derivatives in medicinal chemistry programs exploring arylpropionic acid scaffolds.
The aryl bromide is a convenient handle for late-stage diversification (e.g., Suzuki/Buchwald couplings) during lead optimization.
The free acid can be converted to its sodium/potassium salts to improve aqueous handling during ADME assays or pre-formulation research. All uses are for laboratory research only.
Physical Properties
Item-specific specifications are not provided in the Product Data. Where values are included below, they are general literature expectations for analogous structures and should be verified against the item’s CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~247.06 g/mol (literature inference from name). Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: ~C9H8BrFO2 (literature inference). Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Many arylpropionic acids crystallize as solids with MP often 70–140 C, literature — highly structure-dependent.)
Boiling point: Not typically reported for aromatic carboxylic acids due to decomposition; Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
pKa (carboxyl): Typically ~4–5 for benzylic/arylpropionic acids (literature generality). Not specified for this item; refer to CoA/Spec Sheet.
LogP: Arylpropionic acids with two halogens often exhibit logP ~2–3 in neutral form (literature generality). Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general behavior):
Organic: Expected good solubility in polar aprotic solvents (DMF, DMSO, NMP), moderate in EtOAc, MeOH, MeCN; limited in hexanes (literature generality for arylpropionic acids).
Aqueous: Low at neutral pH; forms water-soluble carboxylate salts at basic pH (literature generality).
Refractive index: Not applicable/rarely reported for solids; Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretive guidance for this compound class (general):
Research grade aryl carboxylic acids are typically suitable for most synthetic applications (amide coupling, esterification, cross-coupling after derivatization). If low UV background or trace metal limits are critical (e.g., for photophysical studies or sensitive catalysis), request an HPLC-grade or metal-screened lot.
Halogenated aromatics can contain trace halide salts or residual metal from synthesis; ICP or metal screening is advisable for ppm-critical catalysis.
Water content and residual solvent control improve reproducibility in coupling reactions; Karl Fischer and GC residual solvent values should be reviewed on the lot CoA when available.
Stabilizers: None are typically added to aryl carboxylic acids; if any stabilizer or inhibitor is used, it will be declared on the CoA/specification. For this item, stabilizers are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As a bifunctional building block, 2-bromo-5-fluorobenzenepropanoic acid supports orthogonal transformations at the aryl bromide, the carboxyl group, and the benzylic chain.
Aryl bromide chemistry (general, literature)
Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira, and Negishi couplings at the 2-bromo position enable rapid diversification to biaryl, aryl amine, aryl alkyne, or alkylated motifs. Typical Pd(0/II) catalysts with phosphine ligands (e.g., Pd(PPh3)4, Pd2(dba)3/XPhos) perform well.
Directed ortho-metalation adjacent to F may be leveraged after masking/derivatizing the acid; Br allows metal–halogen exchange (e.g., with iPrMgCl·LiCl) for further functionalization.
Carboxylic acid chemistry
Efficient amidation using EDC/HOBt, HATU, PyBOP, or acid chloride formation (SOCl2, (COCl)2) followed by amine coupling; esterification via Fischer (ROH/H+), Steglich (DCC/DMAP), or Mitsunobu routes.
Decarboxylative strategies (literature): Access to benzylic radicals or cross-couplings via redox-active esters (NHP esters) using Ni/Pd photocatalytic manifolds.
Benzylic chain modifications
Alpha-functionalization via enolate chemistry (e.g., acylation, halogenation) after temporary esterification; hydrogenolysis/hydrogenation to tune saturation if additional unsaturation is introduced in later steps.
Application domains (research)
Library synthesis for SAR around arylpropionic acid pharmacophores (no clinical claims); agrochemical intermediate exploration; materials precursors introducing halogen handles and acidic functionality.
Practical tips
Protect the acid (as methyl/benzyl ester) for metalation or strong-base couplings to prevent salt formation. Use anhydrous conditions and rigorously exclude water in peptide-type couplings for optimal yields.
Reaction Conditions
Typical literature conditions for this class of substrates; optimize per substrate and scale. Values below are general guidance, not item-specific specifications.
Form N-hydroxyphthalimide ester (DIC/DMAP), then couple under Ni/photoredox (e.g., NiCl2·glyme, bipyridine, Ir(ppy)3) in MeCN or DMA, blue LEDs, RT–35 C, 6–24 h.
Notes: Protect the acid when strong bases/organometallic reagents are used; water content and base identity significantly impact coupling rates and selectivity.
Safety and Handling
Safety details are not provided in the Product Data; consult the SDS for authoritative guidance. The notes below reflect general hazards for aryl halide carboxylic acids.
GHS information (item-specific):
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
Likely hazard profile (general/literature)
May cause skin/eye irritation and respiratory irritation as dust or aerosols.
Combustible organic solid; aryl bromides can emit HBr/HF and CO/CO2 upon thermal decomposition.
PPE and engineering controls (best practice)
Wear lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust/vapors.
Incompatibilities (general)
Strong oxidizers; strong bases/acids may cause hydrolysis/saponification or salt formation; moisture/alkali promote carboxylate formation.
First aid (overview; defer to SDS)
Skin/eyes: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical evaluation if irritation persists.
Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Handling tips
Minimize dust; use clean, dry tools. For coupling chemistry, keep anhydrous until intentional neutralization/activation.
Solvent Selection
This product is an arylalkyl carboxylic acid (weak acid) with a halogenated aromatic ring. Solvent choice will depend on the operation (purification vs. reaction vs. formulation).
Polarity/miscibility profile (general)
Neutral form: Moderately polar; dissolves well in polar aprotic media (DMF, DMSO, NMP) and moderately in EtOAc, MeOH, acetone, MeCN; poor in alkanes.
As carboxylate salt: High aqueous solubility in basic media (e.g., NaOH, Na2CO3 solutions), facilitating extractions or separations.
Selection for typical tasks
Amidation/esterification: DMF, DCM, THF, or MeCN are typical; add coupling reagents (e.g., HATU/EDC) and a base (DIPEA). For greener options, see “Green Alternatives.”
Cross-coupling on the aryl bromide: Toluene, dioxane, THF, CPME, or Me-THF with water or alcohol co-solvents as needed; bases such as K3PO4, Cs2CO3, or NaOtBu.
Chromatography: Elute on silica with gradients of hexanes/EtOAc or toluene/EtOAc; add small % acetic acid or 0.1% TFA if tailing due to acid–silica interactions.
Comparison to alternatives (general)
Versus benzoic acids: Slightly greater solubility in organic media due to the propyl linker; acidity similar.
Versus more heavily halogenated analogs: Typically lower density and slightly higher solubility; reactivity at the C–Br bond remains favorable.
Storage and Reconstitution
Storage (from Product Data): Store at room temperature. Protect from moisture and strong light as a general precaution for halogenated aromatics and carboxylic acids.
Shipping (from Product Data): Shipped under normal conditions.
Reconstitution/solubility (general guidance; not item-specific)
Expected to dissolve readily in DMSO, DMF, and NMP; moderately in EtOAc, MeOH, MeCN, acetone; sparingly in nonpolar hydrocarbons. Solubility increases upon conversion to salts in basic aqueous media.
For moisture-sensitive operations (e.g., coupling to acid chlorides), dry the solid under vacuum (30–50 C) and use anhydrous solvents.
Stability considerations (general)
Carboxylic acids are typically stable at ambient conditions; avoid prolonged exposure to strong bases/acids unless intended. Aryl bromide is stable but should be kept away from strong nucleophiles if undesired substitution is possible.
Packaging and handling
Reseal tightly after use. If long-term storage is planned, consider desiccation. For analytical work, equilibrate to room temperature before opening to minimize condensation.
For any lot-specific limits (water content, residual solvents, assay), Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Intro: 2-Bromo-5-fluorobenzenepropanoic acid is an aryl–alkyl carboxylic acid bearing two halogens on the aromatic ring, making it a versatile bifunctional building block for cross-coupling and acylation chemistry.
Item-specific identifiers (from Product Data)
SKU: B299494
CAS: 1003048-71-2
CID: 43523007
InChIKey: 39771 (truncated/not a standard-length InChIKey)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Name interpretation (general/literature): The name “2-bromo-5-fluorobenzenepropanoic acid” commonly denotes 3-(2-bromo-5-fluorophenyl)propanoic acid: a benzene ring substituted by Br at the 2-position and F at the 5-position, bearing a propanoic acid side chain (–CH2–CH2–CO2H) at the 1-position.
Functional groups and features (general)
Aryl bromide (reactive in Pd-catalyzed cross-couplings, lithiation/metal–halogen exchange).
Aryl fluoride (strong C–F bond; can direct ortho-metalation; limited SNAr unless additionally activated).
Carboxylic acid (amenable to amidation/esterification; can be converted to acyl chlorides, anhydrides, or activated esters).
Molecular formula and mass (literature inference based on name): MF ~ C9H8BrFO2; MW ~ 247.06 g/mol. Not specified for this item; refer to CoA/Spec Sheet.
2D structural description (general)
A benzene ring with Br ortho to the benzylic propanoic acid side chain; F meta to the side chain (at the 5-position). The side chain is saturated (–CH2–CH2–CO2H), terminating in a carboxyl group; no stereocenters are present.
Synthetic Utility
Key reactive elements embedded in 2-bromo-5-fluorobenzenepropanoic acid enable convergent route design.
Functional group leverage
Aryl bromide: Cross-coupling to install diverse motifs (aryl, heteroaryl, vinyl, alkynyl, amine). Bromide offers a favorable balance of reactivity/selectivity compared to chloride/iodide.
Aryl fluoride: Serves as a directing group for ortho-metalation; can participate in SNAr only with additional ring activation. Retaining F can improve lipophilicity and C–H acidity near the ring.
Carboxylic acid: Platform for amide/ester libraries; activation via CDI, EDC, or acid chlorides. Redox-active esters enable decarboxylative couplings (Ni/photoredox).
Protecting-group strategy
Convert to methyl/benzyl esters to traverse strong-base or organometallic steps; deprotect via saponification or hydrogenolysis (Bn).
Retrosynthetic disconnections (general)
Dissect at the aryl–Br position to a 5-fluoro-2-substituted arene coupling partner; or disconnect at the carboxyl C–O to late-stage amidation/esterification. Benzylic chain can be traced back to an arylacrylate hydrogenation or alkylation of an arylacetic precursor.
Purification/workup
Exploit acid/base extraction to separate from neutral/amine-containing byproducts; silica with acid modifiers reduces tailing.
Target Specificity
This product is a small-molecule chemical building block, not a biological targeting reagent.
Antigen/epitope/clone/isotype: Not applicable.
Species reactivity: Not applicable.
Item-specific targeting details: Not specified for this item; refer to CoA/Spec Sheet.
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