This compound belongs to the class of organic compounds known as 3-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 3-position of the benzene ring.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Punto di fusione (°C)
138-141
Peso molecolare
218.020 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
216.954 Da
Monoisotopic Mass
216.954 Da
Topological Polar Surface Area
43.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
165.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Not applicable. No immunoassay, imaging, or molecular biology application protocols are associated with this small-molecule building block in the Product Data.
General handling suggestion (chemistry): prepare analytical stock solutions in dry DMSO or DMF (e.g., 10–100 mM), filter if needed (PTFE, 0.2 µm), and store aliquots to minimize freeze–thaw cycles.
Biological Roles
Item-specific biological testing or functional roles are Not specified for this item; refer to primary literature if needed.
General context (non-clinical, research only):
Structural class: small-molecule aromatic amide with aryl fluorine and bromine. Not known as a natural metabolite or cofactor.
Utility in chemical biology/medchem discovery:
Serves as a synthetic intermediate to prepare fluorinated/brominated anilides and biaryl amides used in SAR campaigns.
The amide motif can participate in H-bonding in protein-ligand interactions; the aryl-F often modulates metabolic stability and binding orientation (design rationale, not a claim of activity).
Labeling/derivatization potential:
Bromide can be elaborated to radiolabel-friendly handles (e.g., boronates for 18F/11C downstream chemistry) via cross-coupling sequences.
ADME-relevant features (theoretical):
Fluorine substitution may alter lipophilicity and block oxidative metabolism at the substituted position; amide reduces basicity and can improve solubility in DMSO for screening stocks.
No biological pathways, targets, or phenotypes are associated with this specific compound in the Product Data. Use strictly for research; do not use in humans or for diagnostic/therapeutic purposes.
Buffer Applications
This compound is a neutral, sparingly water-soluble aromatic amide and is not used as a buffer component. It does not provide acid/base pairs suitable for maintaining physiological pH ranges.
Practical guidance:
For aqueous assays, dissolve first in a co-solvent (e.g., DMSO) to prepare concentrated stocks before dilution into buffer, ensuring final DMSO content remains compatible with the system.
Select standard buffering systems (e.g., phosphate, HEPES, MOPS) for pH control; this compound plays no role in buffering capacity.
Green Alternatives
Greener choices center on solvent and catalyst/base selection during transformations using this building block rather than the substrate itself.
Solvent substitutions (general guidance):
Replace dioxane/DMF with 2-MeTHF, CPME, or toluene/EtOH biphasic systems for Suzuki couplings, when compatible with solubility and temperature.
For polar needs, consider propylene carbonate or Cyrene (dihydrolevoglucosenone) as DMF/DMSO alternatives in some coupling/SNAr protocols.
Bases and additives:
Aqueous K2CO3/K3PO4 in mixed green solvents can reduce DMF load; carbonate bases are less hazardous than alkoxides.
Energy efficiency:
Microwaves or flow chemistry can shorten reaction times and reduce solvent volumes; continuous flow improves heat/mass transfer in couplings.
Note: Validate catalyst/ligand systems in greener media (e.g., Pd-precatalysts with dialkylbiarylphosphines tolerating 2-MeTHF/aqueous bases). Optimize temperature to balance rate and EHS considerations.
Pharmaceutical Uses
Item-specific pharmacopeial status, excipient roles, or GMP applicability are Not specified for this item; refer to CoA/Spec Sheet.
General research/manufacturing context (no therapeutic claims):
Synthetic intermediate: 5-bromo-2-fluorobenzamide can serve as a precursor to drug-like scaffolds via selective functionalization of the aryl bromide (cross-coupling) and, under more forcing conditions, the aryl fluoride (SNAr or metal-catalyzed defluorinative processes).
Scaffold features valued in discovery chemistry: aryl-F for tuning metabolic stability and binding, amide for hydrogen-bonding capacity, and a programmable handle (Ar–Br) for library expansion (biaryl, diaryl ether, aniline derivatives, etc.).
Development considerations: for any use in regulated settings, define impurity profiles (halide-containing byproducts, hydrolysis to the corresponding acid/aniline derivatives) and establish robust analytical methods (HPLC-UV, LC–MS) and residual solvent limits in accordance with ICH guidelines.
This product is sold strictly for research use only and is not an active pharmaceutical ingredient (API) or excipient as per the provided Product Data.
Physical Properties
Item-specific physical specifications (appearance, mp, bp, density, solubility, refractive index, UV cutoff, elemental limits, residual solvents) are Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for reference only (not product specifications):
Phase at ambient conditions: typically a crystalline solid for related halo-benzamides (literature trend).
Polarity/logP: aromatic amides commonly exhibit moderate polarity with reduced aqueous solubility and good solubility in polar aprotic organics (DMF, DMSO, acetonitrile) and chlorinated solvents; aryl halogens increase lipophilicity (literature trends).
Solubility (qualitative, literature): often soluble in DMSO, DMF, DMAc, NMP; variably soluble in EtOAc/MeCN; limited in hexanes/water for comparable analogs.
Practical notes (general chemistry guidance):
Amide engages in intramolecular H-bonding/conjugation that can elevate melting points vs corresponding anilides (trend).
The C–F bond is strong (high BDE) and chemically inert in many settings; the C–Br is significantly more reactive, enabling selective cross-coupling at bromide while retaining fluoride.
Always consult the item’s CoA/SDS for measured physical constants and handling limits.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: None indicated in the Product Data. If present, they would be declared on the CoA.
How to interpret grades (general guidance):
Research or ≥98% purity grades are commonly used for cross-coupling and library synthesis; lower UV-absorbing impurities are preferred for analytical development.
“AR/ACS” indicates conformance with analytical reagent standards; “HPLC grade” applies to solvents rather than solids but, when stated for solids, implies low UV-active/fluorescent impurities helpful for chromatographic assays.
Quality considerations specific to halogenated benzamides (general):
Residual metal content is typically not critical for use as a substrate, but may matter for trace analysis workflows; consult ICP data on the CoA if relevant.
Water content impacts only hygroscopic materials; benzamides are usually not strongly hygroscopic, yet Karl Fischer values may be provided on request.
Structural identity should be supported by 1H/13C NMR, HRMS, and HPLC/GC purity. For coupling applications, monitor for debrominated or hydrolyzed impurities.
Always verify batch-specific specifications (assay, purity method, residual solvents, elemental analysis) on the CoA before regulated use.
Reaction and Applications
As a halogenated benzamide, 5-bromo-2-fluorobenzamide is a versatile building block offering orthogonal aryl halide reactivities and an amide directing group.
Cross-coupling at Ar–Br (preferred site):
Suzuki–Miyaura: install aryl/heteroaryl/alkenyl fragments using Pd(0/II) catalysts; amide directs minimal, but ortho-F can subtly affect electronics.
Buchwald–Hartwig amination: convert Ar–Br to anilines; selectivity over Ar–F typically high.
Sonogashira/Heck/Negishi/Kumada: engage bromide with appropriate partners; C–F remains intact.
Nucleophilic aromatic substitution (SNAr) at Ar–F:
Possible under strong conditions with good nucleophiles if the ring is sufficiently activated by the amide and positional electronics; ortho-amide can assist via H-bonding/conjugation.
Directed metalation/functionalization:
The amide can act as a directing group for ortho-metalation enabling further substitution, though halides constrain positions; lithiation strategies require low temperatures and careful quench.
Late-stage diversification:
Use bromide for initial coupling, retain fluoride for a second-stage SNAr/metal-catalyzed defluorinative coupling or Balz–Schiemann-type derivatizations (indirect routes).
Applications (general):
Medicinal chemistry scaffolding: introduction of fluorine and amide motifs for metabolic tuning (research context only).
Materials/ligand design: halogenated aromatics as precursors to functionalized polymers and ligands.
Practical tips: dry, degassed solvents and bases (e.g., K3PO4, Cs2CO3) improve couplings; bromide typically reacts at milder conditions than fluoride, enabling chemoselective transformations.
Reaction Conditions
General literature guidance (illustrative, not product-specific specifications):
Suzuki–Miyaura coupling (at Ar–Br):
Catalyst: Pd(dppf)Cl2·DCM (1–3 mol%) or Pd2(dba)3 + XPhos/SPhos.
Base: K3PO4 (2–3 equiv) or Cs2CO3; aqueous conditions improve turnover.
Solvent: 1,4-dioxane/H2O, 2-MeTHF/H2O, toluene/H2O; 60–100 C, 1–12 h.
Notes: Ar–F remains intact; adjust temperature for solubility.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd-precatalyst (e.g., XPhos, BrettPhos) 1–3 mol%; NaOtBu or K3PO4 as base.
Solvent: tBuOH, toluene, dioxane, or CPME; 80–110 C, 4–18 h.
Notes: Choose ligand to match amine nucleophile; avoid conditions that promote amide N-arylation (rare under standard conditions).
Sonogashira:
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) ± CuI (2–5 mol%); Et3N or DIPEA base.
Solvent: THF, DMAc, or 2-MeTHF; 40–80 C, 2–12 h.
SNAr at Ar–F (if feasible):
Nucleophile: amines/alkoxides; Base: NaH/KOtBu.
Solvent: DMSO, NMP; 80–140 C, 6–24 h.
Notes: Ring activation and regiochemistry govern success; monitor closely.
Workup/purification:
Quench with water/brine; extract with EtOAc/MTBE; silica gel chromatography. Residual palladium may be removed with metal scavengers if needed.
These are starting-point conditions; optimize for scale, solubility, and EHS constraints.
Safety and Handling
Item-specific GHS signal word, hazard statements, pictograms, and classification are Not specified for this item; refer to the product SDS for authoritative safety information.
General safety guidance for halogenated benzamides (non-authoritative):
Likely hazards: may cause skin/eye irritation; harmful if swallowed or inhaled (typical for aromatic amides). Avoid dust generation.
PPE: lab coat, nitrile gloves, safety glasses; use a fume hood for weighing/handling to minimize inhalation of particulates.
Incompatibilities: strong oxidizers (general), strong bases or acids under forcing conditions may hydrolyze the amide; avoid reagents that promote uncontrolled halogen exchange.
Thermal stability: aromatic amides are generally thermally stable solids; avoid excessive heating without ventilation.
First aid (overview):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Environmental: prevent release to the environment; halogenated organics may be persistent.
Peroxide formation: not applicable (no ether functionality). For all operations, defer to the current SDS and institutional EHS protocols.
Solvent Selection
This compound is an aromatic amide bearing aryl Br and F; it behaves as a moderately polar, largely non-ionizable substrate.
Polarity/miscibility (general trends):
Good solubility: DMSO, DMF, DMAc, NMP; often soluble in chlorinated solvents (DCM, chlorobenzene) and EtOAc; variably soluble in MeCN; limited in alkanes and water.
Hydrogen bonding: amide NH/C=O engage in H-bonding; protic solvents (MeOH, EtOH) may dissolve it moderately but can participate in side reactions under strong activation.
Typical use scenarios:
Cross-coupling at Ar–Br: polar aprotic solvents (DMF, dioxane, toluene/dioxane, CPME, 2-MeTHF) with base and Pd catalyst.
SNAr at Ar–F (if activated by amide ortho/para and suitable conditions): high-boiling polar solvents (DMSO, NMP) and strong bases/nucleophiles.
Amide remains intact under neutral conditions; avoid strongly basic hydrolysis in aqueous alcohols when the amide must be preserved.
Practical selection tips:
Begin solubility assessment at 10–50 mg/mL in DMSO or DMF for stock solutions (analytical or screening).
For scale-up couplings, consider 2-MeTHF or CPME as greener alternatives to dioxane/DMF; use higher temperatures to compensate for lower polarity.
For reactions sensitive to water, dry solvents (molecular sieves or distillation) improve reproducibility.
Always verify solubility empirically for your lot and process temperature.
Storage and Reconstitution
Storage (item-specific): Room temperature (per Product Data). Protect from moisture and prolonged light exposure. Keep container tightly closed.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Stability: Item-specific stability data and retest period are Not specified for this item; consult the CoA.
General guidance for halogenated benzamide solids:
Store in a desiccator or with desiccant in the original amber vial if provided.
Avoid strong acids/bases and oxidizers in storage areas.
For solution preparation: dissolve in anhydrous DMSO, DMF, or suitable organic solvent. Typical research stocks: 10–100 mM in DMSO; filter through 0.2 µm PTFE if particulate is present.
Aliquot solutions to minimize air/moisture exposure; inert-gas blanket (N2/Ar) can extend solution shelf-life in reactive media.
Aqueous solubility is limited; if dilution into buffer is required, add organic co-solvent first and mix thoroughly to prevent precipitation.
Always refer to the current CoA/SDS for batch-specific storage limits and stability information. For long-term needs, confirm solution stability by LC–MS/HPLC over time at intended storage conditions.
Structure and Identity
5-Bromo-2-fluorobenzamide is a halogenated benzamide building block featuring an amide handle and two aryl halogens of differentiated reactivity (Ar–Br, Ar–F).
Item-specific identifiers (from Product Data)
CAS: 214210-17-0
SKU: B1067784
Storage Conditions: Room temperature
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (for reference; not item specifications)
Typical molecular formula (literature): C7H5BrFNO
Typical formula weight (literature): ~218.02 g/mol
Ring/system: monosubstituted benzamide core with 1,2,5-substitution pattern (amide at C1 by convention, F at C2, Br at C5)
Stereochemistry: none (achiral)
2D structural description (general)
A benzamide ring bearing an ortho-fluoro substituent relative to the amide carbonyl and a meta-bromo substituent (para to the ortho-fluoro). The amide carbonyl is conjugated with the aryl ring, enabling resonance stabilization and potential directing effects in metalation and cross-coupling.
Synthetic Utility
Key reactivity elements:
Aryl bromide: highly versatile for Pd-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Heck). Provides chemoselective site for initial diversification while preserving Ar–F.
Aryl fluoride: robust under most coupling conditions; can be engaged in SNAr with strong nucleophiles or in specialized defluorinative functionalizations.
Amide group: offers hydrogen bonding and mild directing ability; withstands many metal-catalyzed conditions and provides a handle for downstream transformations (e.g., N-acyl to N-alkyl via Curtius-like pathways after conversion to acid, or reduction to anilide via amide reduction strategies).
Suzuki–Miyaura: Ar–B(OH)2/boronate esters → biaryls; bases such as K3PO4/Cs2CO3 in dioxane/H2O, 2-MeTHF/H2O.
Buchwald–Hartwig amination: primary/secondary amines to give diarylamines; dialkylbiarylphosphine ligands improve rates.
Sonogashira: terminal alkynes to aryl alkynes; Cu co-catalyst optional with modern Pd systems.
SNAr: displacement of Ar–F by amines/alkoxides in DMSO/NMP at elevated temperature when electronics permit.
Electrophilic aromatic substitution: generally deactivated by amide/fluoro; halogen–metal exchange at Ar–Br is possible under cryogenic conditions for further elaboration (exercise caution to avoid amide lithiation/hydrolysis).
Strategic value: orthogonal halogens enable two-stage diversification sequences (first bromide, then fluoride), facilitating rapid parallel synthesis and late-stage analog generation.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an affinity reagent, biologic, or targeted probe. No antigen/epitope, clone, isotype, or species reactivity information applies.
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