This compound belongs to the class of organic compounds known as 2-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 2-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
Peso molecolare
216.030 g/mol
XLogP3
0.500
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
214.958 Da
Monoisotopic Mass
214.958 Da
Topological Polar Surface Area
49.300 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
151.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
Not applicable for this product type.
No validated immunoassay or cell-based assay protocols are provided for this small-molecule reagent. Any application-specific procedures (e.g., cross-coupling, O‑acylation) should follow standard organic synthesis protocols as outlined under Reaction Conditions and Synthetic Utility.
Biological Roles
General biochemical context (literature; not product-specific, no clinical claims)
Hydroxamic acids are strong bidentate ligands (C=O and N–O−) for many metal ions (Fe3+, Cu2+, Zn2+). This underpins their use as metal-binding motifs in coordination chemistry and as probes of metalloenzyme active sites in research settings.
Aromatic hydroxamates can form stable ferric complexes reminiscent of siderophore interactions, influencing redox and spectroscopic properties.
Acid–base behavior: At physiological pH, partial deprotonation of the N–OH can occur (pKa ~8–9 for related hydroxamates), modulating membrane permeability and metal affinity.
Reactivity in biological media: Susceptible to hydrolysis under strong acidic/basic conditions and to transacylation in the presence of activated acyl donors; stable near neutral pH, particularly when protected from esterases and metals that catalyze transformations.
Implications for laboratory studies
When used as a metal chelating probe, pre-treat buffers with metal scavengers (Chelex) to control background binding.
Prepare fresh DMSO stocks and avoid prolonged exposure to strong nucleophiles to minimize decomposition. No medical or therapeutic use is implied; for research use only.
Buffer Applications
Not typically used as a buffering agent.
This compound is a functionalized aromatic hydroxamic acid, not a classical buffer component. It lacks a broad, flat buffering range and is generally employed as a building block or ligand.
For experiments in aqueous media, select a suitable biological buffer (e.g., phosphate, HEPES, Tris) and dissolve the compound first in a compatible co-solvent (DMSO/MeOH), then dilute into the buffer while monitoring for precipitation.
Green Alternatives
Perspective
As a solid building block, “green” considerations focus on coupling methods, solvents, and bases rather than substituting the molecule itself.
Greener method choices (literature)
Solvents: Favor 2-MeTHF, CPME, or water/ethanol blends over DMF/DMSO where feasible. Micellar catalysis (aqueous surfactant media) can enable Suzuki couplings at room temperature using ppm Pd.
Catalysts: Employ ligand-enabled low-Pd loading or Ni-catalysis to reduce precious metal use. Heterogeneous Pd on reusable supports can aid recovery.
Bases: K3PO4, K2CO3, or Na2CO3 in water or alcoholic media are milder and safer than strong alkoxides.
Energy: Microwave or flow chemistry can shorten reaction times/temperatures, improving energy efficiency.
Trade-offs
Hydroxamate chelation may inhibit catalysts more in aqueous media; additional ligand or catalyst loading may be needed.
Less polar solvents (2-MeTHF/CPME) can lower substrate solubility; co-solvent strategies (2-MeTHF/water) mitigate this.
Quick comparison (literature, qualitative)
DMF: High solubility, difficult EHS profile, high boiling point.
2-MeTHF: Renewable, easier workup, lower polarity; may require heating or co-solvent.
Micellar water: Excellent EHS, minimal solvent waste; requires surfactant and careful base selection to preserve hydroxamate integrity.
Pharmaceutical Uses
Formulation/CMC context (general; no therapeutic claims)
Not a known pharmacopeial excipient. The hydroxamic acid motif is common in research intermediates targeting metal-binding sites, but this listing is for research and process development only.
Potential roles in development labs:
Synthetic intermediate toward ureas/carbamates via Lossen rearrangement.
Ligand component in metal-complex screening libraries (analytical or discovery research).
If incorporated into dosage-form research, consider:
Control of residual metals (due to chelation) to avoid variability in analytical assays.
Use of co-solvents (DMSO/PEG400) for solution studies; confirm stability in the intended pH range.
Regulatory note
No pharmacopeial monograph or excipient grade is indicated for this item. Any GMP or clinical use would require independent qualification. For research use only.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature (informational; not item specifications)
State/phase: Typically a crystalline solid for analogous aromatic hydroxamic acids
Molecular formula: C7H6BrNO2 (literature)
Molecular weight: ~216.03 g/mol (literature)
Acid-base: Hydroxamic acids are weak acids; pKa (N–OH deprotonation) typically ~8–9 (literature, class-general)
Solubility profile (qualitative, literature):
Good solubility in polar aprotic organics (DMSO, DMF, NMP)
Moderate in alcohols (MeOH, EtOH)
Limited in water at neutral pH; solubility increases in basic media due to deprotonation
Partitioning: Aromatic hydroxamates with a single bromo substituent show moderate hydrophobicity; expect modest logP typical of bromobenzamide analogs (literature, qualitative)
Melting/boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Notes for use
Prepare concentrated stock solutions in dry DMSO or DMF for reliability.
The hydroxamic acid can form strong complexes with transition metals, affecting apparent solubility in metal-containing media.
Quality and Grades
Item-specific (from Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research/technical grade: Typically suitable for synthetic chemistry and method development; may contain trace inorganic/organic impurities. Verify metals if catalysis is planned due to hydroxamate–metal interactions.
Chromatography suitability: If using for analytical calibration or bioassays, consider HPLC/GC assay verification and residual solvent/metals testing.
Stabilizers/additives: None specified for this item. Hydroxamic acids generally do not require stabilizers; however, dryness and protection from strong acids/bases help maintain integrity.
Best practices for QC in your lab
Identity: Confirm by 1H/13C NMR (DMSO‑d6 often optimal), IR (C=O ~1650–1680 cm−1; N–O stretch ~900–950 cm−1, literature), and HRMS.
Purity: Assess by HPLC/UPLC with UV at ~210–280 nm; inspect for O‑acylated or hydrolyzed byproducts.
Residual metals: If subsequent cross-couplings are planned, ICP-MS screening for Pd/Cu/Ni can be prudent.
Water content/peroxide/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
General synthetic roles (literature)
Bifunctional handle:
Aryl bromide enables C–C/C–N/C–S bond formation via Pd/Ni-catalyzed cross-couplings (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig). This allows rapid diversification of the 2-substituent while retaining the hydroxamate.
Hydroxamic acid functions in metal chelation, O/N‑acylation chemistry, and as a precursor to isocyanates via Lossen rearrangement (after O‑activation).
Representative applications
Library synthesis of ortho-substituted benzohydroxamates by Suzuki coupling with boronic acids/esters, maintaining the hydroxamate intact under mild base (e.g., K2CO3).
Site-selective O‑acylation (e.g., with acyl chlorides/anhydrides) to generate O‑acyl hydroxamates that undergo Lossen rearrangement to isocyanates, which can be trapped by alcohols/amines to furnish carbamates/ureas.
Directed ortho-metalation is less applicable due to the bromide; however, the hydroxamate can act as a directing/chelating auxiliary in certain C–H functionalizations (literature precedents exist with related benzamides).
Formation of hydroxamate esters/ethers via Mitsunobu or alkylation (selectivity O vs N can be tuned by base/solvent), enabling protecting-group strategies or rearrangement pathways.
Practical tips
Maintain mild basicity (carbonate/tertiary amines) to avoid hydrolysis during cross-coupling; monitor for dehydroxylation under forcing conditions.
If chelation poisons catalysts, add ligand-rich conditions (e.g., SPhos/XPhos) or pre-activate catalyst; consider temporary O-acylation to attenuate binding in challenging couplings.
For Lossen chemistry, ensure anhydrous conditions; prepare and use O‑activated intermediates in situ.
Reaction Conditions
Illustrative conditions (literature examples; adjust per substrate and scale)
Suzuki–Miyaura coupling (aryl bromide):
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-PEPPSI/IPr systems (0.5–1 mol%)
Base: K2CO3 or K3PO4 (2–3 equiv)
Solvent: 1,4-dioxane/water (3:1), EtOH/water, or 2-MeTHF/water
Temp/time: 60–90 °C, 2–8 h; monitor by HPLC. Hydroxamate typically tolerated under these mild basic conditions.
Sonogashira coupling:
Catalyst: PdCl2(PPh3)2 (1–2 mol%) with CuI (5–10 mol%) or Cu-free Pd/XPhos systems
Base: Et3N or DIPEA; solvent: THF, MeCN, or i-PrOH
Temp: rt–60 °C, 2–12 h. Avoid strong base excess to limit N–O cleavage.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) with BrettPhos/SPhos (2–4 mol%)
Base: NaOtBu or Cs2CO3 (1.5–2.0 equiv)
Solvent: t-AmylOH, toluene, or dioxane; 60–100 °C. Screen milder bases first to protect the hydroxamate.
O‑Activation: Treat with p-nitrophenyl chloroformate or carbonyldiimidazole (CDI) in dry DCM/THF at 0–25 °C
Rearrangement: Warm to 25–60 °C; trap isocyanate with ROH/RNH2 to give carbamates/ureas. Keep anhydrous to avoid hydrolysis.
Workup notes
Chelation can retain Pd/Cu; include metal scavengers (silica-thiol, QuadraPure) or hot filtration through carbon/celite.
Monitor for hydrolysis by LC; neutral to mildly basic aqueous workups are preferred.
Safety and Handling
Item-specific (from Product Data)
GHS classification, pictograms, H-statements, signal word: Not specified for this item; refer to SDS.
Storage conditions: Room temperature. Store tightly closed.
General safety guidance (literature; consult SDS for authoritative instructions)
Likely hazards: Irritation to skin/eyes/respiratory tract is possible for aromatic amide/hydroxamate solids. Avoid dust generation and inhalation.
PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves. Use in a fume hood to avoid dust/vapor exposure.
Incompatibilities: Strong oxidizers; strong bases/acylating agents can induce O- or N-acylation and rearrangements. Avoid prolonged contact with strong acids/bases which can hydrolyze hydroxamic acids.
Reactivity notes: Hydroxamic acids chelate metals (Fe3+, Cu2+, etc.); metal contamination can influence stability and reactions. Dry conditions minimize unintended acyl transfer or hydrolysis during synthesis.
First aid overview:
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
Spill/cleanup: Avoid dust; collect mechanically; wash area with appropriate solvent/detergent while observing compatibility.
Fire: Use standard extinguishing media (CO2, dry chemical, foam). Combustion may produce CO/CO2, HBr, NOx.
Solvent Selection
Applicability
This product is a polar aromatic solid (hydroxamic acid). Focus on dissolution for reaction/media preparation rather than solvent replacement.
Limited: Water at neutral pH (increase solubility by slight basification to form hydroxamate anion)
Avoid: Nonpolar solvents (hexanes, toluene) unless used as part of biphasic systems or after derivatization
Selection tips
For stock solutions in screening: Prepare 10–100 mM in dry DMSO; dilute into assay buffers last to minimize precipitation.
For cross-couplings on the aryl bromide: Employ mixed solvents such as 1,4-dioxane/water, MeOH/water, or CPME/water under Pd catalysis (literature). The hydroxamate tolerates mild base but avoid strong base excess to prevent hydrolysis.
For acyl-transfer chemistry (O-acylation, Lossen precursors): Use dry aprotic solvents (DCM, THF, EtOAc, MeCN) and mild bases.
Polarity context (literature)
Functional groups confer H-bond donor/acceptor capacity; dielectric environments >25 (DMSO/DMF) favor dissolution; protic solvents can engage in H-bonding, altering reactivity.
Storage and Reconstitution
Item-specific (from Product Data)
Storage: Room temperature
Shipping: Normal
General guidance
Keep container tightly closed in a dry, well-ventilated place. Protect from strong acids/bases and oxidizers.
Hygroscopicity: Aromatic hydroxamates are typically not strongly hygroscopic, but drying under vacuum before moisture-sensitive steps is recommended.
Reconstitution/preparation of stocks:
For synthetic use: Weigh solid quickly to minimize ambient moisture uptake. If needed, dry at ≤40 °C under vacuum.
For solution stocks: Dissolve in anhydrous DMSO or DMF to 10–100 mM; filter (0.2 µm PTFE) for analytical work.
For aqueous systems: Dilute DMSO stock into buffer while vortexing; final organic co-solvent 0.5–2% v/v typically avoids precipitation. Slight basification (pH 8–9) can improve solubility but may increase hydrolysis risk; optimize empirically.
Stability notes (literature): Hydroxamic acids are generally stable at neutral pH and ambient temperature but can hydrolyze under strong acidic/basic conditions or undergo acyl transfer when exposed to reactive acylating agents.
For long-term storage: Minimize light exposure, store in amber container if possible, and reseal promptly with desiccant present in the outer container.
Structure and Identity
Item-specific (from Product Data)
SKU: B1313030
Product name: 2-bromo-N-hydroxybenzamide
Storage conditions: Room temperature
Shipped in: Normal
Research use: For research use only
Computed/Literature (informational; not item specifications)
Common name/description: 2-bromobenzohydroxamic acid (aromatic hydroxamic acid bearing an ortho-bromo substituent)
Molecular formula (literature): C7H6BrNO2
Molecular weight (literature): ~216.03 g/mol
Structural features:
Aromatic ring (benzene) bearing an ortho (2-) bromo substituent
Functional group handles: aryl bromide (for cross-coupling) and hydroxamic acid (for chelation/rearrangements)
SMILES (literature): O=C(NO)c1ccccc1Br
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
2D structural description (verbal)
A benzene ring substituted by bromine at the position adjacent to the amide carbonyl. The carbonyl is directly attached to the ring (benzoyl), and the amide nitrogen bears a hydroxyl group (hydroxamic acid), enabling bidentate metal binding via C=O and N–O.
Synthetic Utility
Functional group leverage (literature)
Aryl bromide:
Suzuki–Miyaura coupling to install aryl/alkenyl groups using boronic acids/esters.
Sonogashira coupling to introduce alkynyl substituents (terminal alkynes) under Pd/Cu or Cu-free Pd systems.
Buchwald–Hartwig amination to form anilines or diarylamines; ligand choice critical to tolerate the hydroxamate.
Hydroxamic acid:
O‑Acylation followed by Lossen rearrangement to generate isocyanates in situ; capture with nucleophiles to yield ureas/carbamates.
Alkylation (O vs N selectivity tunable) to access protected hydroxamates or rearrangement precursors.
Metal chelation for directed transformations or as a removable directing group in select C–H activations (substrate-dependent).
Retrosynthetic value
Serves as a convergent node where ring functionalization is accomplished via cross-coupling, while the benzohydroxamate handle can be transformed downstream into diverse nitrogen-containing motifs.
Selectivity and protection
Temporary O‑protection (e.g., O‑benzyl, O‑acetyl) can attenuate chelation and improve compatibility with catalytic systems; deprotection conditions should spare the aryl bromide or subsequent substituents.
Maintain mild bases (carbonate/tertiary amine) to avoid hydrolysis of the hydroxamate during coupling or workup.
Target Specificity
Not applicable for this product type.
This is a small-molecule building block, not an antibody, enzyme, or biologic. No antigen/epitope/isotype or species reactivity data apply to this item.
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