2-[(3-Bromophenyl)methoxy]-Benzoic acid - ≥97% , CAS No.743453-43-2

CAS: 743453-43-2 Cat. No.: B708632 Fórmula: C₁₄H₁₁BrO₃ Peso molecular: 307.15 Número CE: 961-993-2 PubChem CID: 3302765

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥97%

Nomes e identificadores

Sorrisos canónicos

C1=CC=C(C(=C1)C(=O)O)OCC2=CC(=CC=C2)Br

IUPAC Name

2-[(3-bromophenyl)methoxy]benzoic acid

InChIKey

XXEHDADBNHDAIB-UHFFFAOYSA-N

INCHI

1S/C14H11BrO3/c15-11-5-3-4-10(8-11)9-18-13-7-2-1-6-12(13)14(16)17/h1-8H,9H2,(H,16,17)

SMILES isoméricas

C1=CC=C(C(=C1)C(=O)O)OCC2=CC(=CC=C2)Br

PubChem CID

3302765

Peso molecular

307.15

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acids
• Alternative Parents: Phenoxy compounds Phenol ethers Benzoyl derivatives Bromobenzenes Alkyl aryl ethers Aryl bromides Carboxylic acids Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoic acid - Phenoxy compound - Phenol ether - Benzoyl - Alkyl aryl ether - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Organohalogen compound - Organobromide - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 307.140 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 305.989 Da
• Monoisotopic Mass: 305.989 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 282.000
• 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

Application Protocols

Not applicable as a validated bioassay reagent. There are no item-specific protocols (e.g., WB, IHC, IF, FC) provided for this small-molecule building block.

General lab use suggestions (context)

• For stock solutions, dissolve in dry DMSO or DMF (e.g., 10–100 mM) for high-throughput screening or as a coupling substrate; filter if necessary.
• For synthetic runs, follow reaction-specific protocols (see Reaction Conditions tab) and adjust solvent/base to accommodate the free acid functionality.

For any specific application, consult the primary literature and validate conditions empirically.

Biological Roles

This compound is a synthetic aromatic carboxylic acid with a brominated aryl ether substituent. It is not known as a natural metabolite or cofactor.

General biochemical considerations (literature/context)

• Ionization: as a benzoic acid derivative, it exists predominantly as the carboxylate at physiological pH, which can influence passive permeability and protein binding in biochemical assays.
• Binding propensity: aromatic acids can engage in hydrogen bonding (via the acid/carboxylate) and π–π/halogen interactions in protein pockets; the meta-bromophenyl may participate in halogen bonding (σ-hole interactions) in structural biology studies.
• Assay use: serves as a fragment-like scaffold or intermediate for preparing ligand libraries; the aryl bromide handle allows rapid diversification for SAR generation.

No biological function or pathway role is established for this specific structure. Any use should be limited to in vitro research, probe synthesis, or materials/chemical biology method development. For all biological testing, ensure appropriate controls and characterize purity and counter-ions/solvents, as these can impact assay readouts.

Research Use Note: For research use only (per product data). Not for human or veterinary use.

Buffer Applications

This product is not a dedicated buffering agent and is not typically used to prepare laboratory buffer systems.

• As a benzoic acid derivative (weak acid, literature pKa for benzoic acids ~4.0–4.5), it could, in principle, contribute buffering capacity near this pH if present at sufficient concentration; however, it is not commonly employed for this purpose due to limited aqueous solubility and lack of standardized buffer recipes.
• For buffer preparation needs, select established systems (e.g., acetate pH 3.6–5.6, citrate pH 3.0–6.2, phosphate pH 6.0–8.0) and consult buffer-focused reagents.

Recommendation: Use this material as a synthetic building block rather than as a buffer component.

Green Alternatives

While the compound itself is a fixed structure, greener choices can be made in its use—particularly in solvent and reagent selection for coupling and amidation steps.

Greener choices (literature/general)

• Solvents:
  • Prefer 2-MeTHF or CPME over THF/1,4-dioxane; EtOAc or Me-THF over DCM where feasible.
  • Aqueous micellar media (e.g., TPGS-750-M) can enable Suzuki couplings at room temperature with reduced organic solvent usage.
• Bases and reagents:
  • For amide formation, use EDC·HCl with Oxyma/HOAt in EtOAc/MeCN or water-tolerant media in place of DCC (avoids DCU waste).
  • Employ catalytic DMAP at minimal loadings; consider CDI-mediated couplings generating CO2/imidazole byproducts.
• Catalysis:
  • Use ligand-optimized Pd at ppm–low mol% loadings; explore Ni catalysis for aryl bromide couplings to reduce precious metal usage.
• Energy efficiency:
  • Room-temperature or flow-enabled couplings to minimize heating; microwave can shorten times and reduce decomposition.

Comparison snapshot (general)

• THF/1,4-dioxane vs 2-MeTHF/CPME: latter are bio-derived/less hazardous and offer better peroxide profiles; note solubility differences and higher bp affecting workups.
• DCM vs EtOAc/Me-THF: EtOAc is less toxic and more biodegradable; partitioning and azeotrope behavior differ, requiring process adjustment.

Trade-offs

• Greener solvents may alter solubility and catalyst activity; small solvent screens are recommended to retain yield/selectivity while reducing environmental impact.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the product data for this item, and it is not a recognized pharmaceutical excipient.

Context for medicinal chemistry (literature/general)

• Role: versatile intermediate for assembling candidate molecules; the aryl bromide allows modular cross-coupling, while the carboxylic acid provides a handle for amide/ester libraries.
• Property tuning: converting the acid to esters, amides, or bioisosteres (e.g., tetrazoles) can modulate solubility, permeability, and metabolic stability during lead optimization.
• Conjugation: the acid can be used to tether the scaffold to linkers, tags, or solid supports for affinity or PROTAC-like tool compound development.

Manufacturing/formulation note

• If incorporated into research formulations (e.g., as a model compound), typical vehicles include DMSO stock solutions diluted into assay buffer or co-solvent systems. Ensure compatibility with assay components to avoid precipitation.

Compliance

• Research Use Only (per product data). Not for use in diagnostic procedures, foods, or drug products.

Physical Properties

Item-specific physicochemical specifications were not provided in the product data. The following are general or literature/structure-derived values provided for scientific context and should not be construed as this item’s specifications.

Item-specific specs

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Literature/structure-derived properties (non-item-specific)

• Molecular formula: C14H11BrO3 (computed from structure)
• Molecular weight: ~307.14 g/mol (computed)
• Acidic functionality: contains a benzoic acid; typical pKa for benzoic acids is ~4.0–4.5 (literature, scaffold-based)
• Lipophilicity: presence of a brominated aryl ether suggests moderate hydrophobicity; benzoic acid reduces overall logP relative to a neutral analog (qualitative, literature trend)
• Solubility (qualitative): expected sparingly soluble in water; soluble in polar aprotic organic solvents (e.g., DMSO, DMF) and moderately in chlorinated/aromatic solvents (DCM, THF, toluene) (literature expectation for similar scaffolds)
• Physical state: many analogous aryl-ether benzoic acids are crystalline solids; specific MP/appearance for this item Not specified for this item; refer to CoA/Spec Sheet.

Not provided for this item (consult CoA/SDS or request): melting point, boiling point, density, refractive index, UV cutoff, water content, residual solvents, metal content.

Quality and Grades

Item-specific grade, purity, and stabilizers are not provided in the product data for SKU B708632.

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades for small-molecule building blocks (for context)

• Research/technical grade: suitable for synthetic R&D where ultra-trace impurities are not critical. Typical assay reported by HPLC or NMR; residual solvents and water may be present at low levels (consult CoA).
• Analytical/AR grade: tighter impurity control, suitable for analytical or sensitive synthetic applications.
• High-purity (>98–99%) building blocks: often preferred for cross-coupling chemistry to minimize side reactions from halide impurities or adventitious metals.

Quality considerations specific to this scaffold (general)

• Aryl bromide integrity: monitor for debromination or hydrolysis during storage or prolonged exposure to high temperatures.
• Acid content/neutralization: verify free acid vs. salt form by NMR/IR; carboxylate salts can impact solubility and coupling conditions.
• Water and residual solvents: dry thoroughly before moisture-sensitive transformations (e.g., acid chloride formation, coupling via in situ activation).

Documentation

• For definitive, item-specific information (assay, impurity profile, residual metal/halide, water, MP), consult the Certificate of Analysis (CoA) associated with the lot shipped.

Reaction and Applications

As a bifunctional building block, 2-[(3-bromophenyl)methoxy]-benzoic acid offers orthogonal reactivity at the aryl bromide and the carboxylic acid. The aryl ether linkage provides conformational spacing between aromatic rings, enabling modular diversification.

Representative application families (literature/general)

• Cross-coupling at the aryl bromide:
  • Suzuki–Miyaura: introduction of aryl/heteroaryl via boronic acids/esters (Pd(0/II), base such as K3PO4, Na2CO3; solvents 1,4-dioxane/H2O, toluene/H2O, or 2-MeTHF).
  • Buchwald–Hartwig amination: convert Ar–Br to anilines using Pd catalysts and dialkylbiaryl phosphine ligands; bases like NaOtBu, Cs2CO3.
  • Sonogashira: install alkynes (Pd/Cu cocatalysis) when alkyne handles are desired.
• Carboxylic acid elaboration:
  • Amide coupling: HATU/HBTU/EDC·HCl with HOAt/HOBt or Oxyma; or acid chloride (SOCl2, oxalyl chloride) followed by amine addition.
  • Esterification: Steglich (DCC/DMAP) or Fischer (alcohol, catalytic acid) to tune lipophilicity/solubility.
  • Decarboxylative strategies: silver- or photocatalyzed decarboxylative cross-couplings to access C–C or C–heteroatom bonds (emerging literature).
• Protective group/salt tactics:
  • Temporary carboxylate salt formation (Na/K) for phase manipulation; benzyl esters as removable protecting groups (hydrogenolysis).

Practical tips

• Maintain anhydrous conditions for acid chloride formation and moisture-sensitive couplings.
• For cross-couplings, ensure base compatibility with the acid (consider preforming a soluble carboxylate or using buffered/aqueous systems to avoid neutralization issues).
• The meta-bromo position on the distal ring typically couples efficiently; oxidative addition to aryl bromides is generally favorable under Pd catalysis.

Reaction Conditions

The following representative conditions are provided as literature-style guidance for the aryl bromide and carboxylic acid functionalities. They are not item-specific specifications.

Suzuki–Miyaura coupling (Ar–Br to Ar–Ar′)

• Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1–2 mol%) with dialkylbiaryl phosphine ligand (e.g., XPhos, SPhos, RuPhos).
• Base: K3PO4, K2CO3, or Na2CO3 (2–3 equiv).
• Solvent: 1,4-dioxane/H2O, toluene/H2O, or 2-MeTHF/H2O; 60–100 °C, 2–16 h.

Buchwald–Hartwig amination (Ar–Br to Ar–NR2)

• Catalyst/ligand: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%) with BrettPhos, tBuBrettPhos, or XPhos.
• Base: NaOtBu, Cs2CO3, or K3PO4.
• Solvent: toluene, dioxane, or CPME; 80–110 °C, 4–18 h.

Sonogashira coupling (Ar–Br to Ar–C≡CR)

• Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) with CuI (5–10 mol%).
• Base: Et3N, iPr2NH, or K2CO3.
• Solvent: THF, DMF, or 2-MeTHF; ambient to 60 °C.

Amide coupling from the acid

• EDC·HCl (1.2–1.5 equiv) + Oxyma or HOBt; base: DIPEA (2–3 equiv).
• Solvent: DMF, MeCN, or EtOAc; 0–25 °C to room temp, 2–16 h.

Acid chloride route

• Reagent: SOCl2 (2–5 equiv), catalytic DMF; solvent: DCM or toluene; reflux until gas evolution ceases, then add amine and base (e.g., pyridine) at 0–25 °C.

Notes

• The free carboxylic acid can interact with catalysts/bases; aqueous biphasic conditions or in situ salt formation often improve outcomes.
• Monitor reactions by LC–MS/HPLC; aryl-aryl ether is generally robust under Pd-catalyzed conditions.

Safety and Handling

Item-specific hazard classification is not supplied in the product data; defer to the SDS for authoritative information.

GHS and hazard statements (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.

General safety considerations for aryl bromide benzoic acids (literature/general guidance)

• Likely hazards: may cause skin/eye irritation and respiratory irritation to dust; avoid inhalation of particulates.
• PPE: lab coat, safety glasses or chemical splash goggles, and suitable gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
• Incompatibilities: strong bases can deprotonate the carboxylic acid forming salts; strong oxidants may react with the aromatic system; avoid strong reducing agents that could affect the aryl bromide under forcing conditions.
• Fire safety: organic solid; combustible. Use CO2, dry chemical, or foam for small fires. Avoid dust accumulation.
• 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 attention for persistent irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.

Waste and spill response

• Collect solids with minimal dust generation; place in suitable container for organic waste. Dispose of according to local regulations.

Always consult the product’s SDS for definitive hazard, exposure limits, and emergency measures.

Solvent Selection

This product is a small-molecule, non-volatile aromatic acid building block rather than a solvent. Solvent selection is therefore discussed in the context of dissolving the compound for synthesis or analysis (general guidance; not item-specific specifications).

Polarity and miscibility (literature expectations)

• Likely good solubility: DMSO, DMF, NMP; moderate in acetone/EtOAc/THF/DCM; limited in hexanes/heptane; low in water as the neutral acid but water-soluble upon basification (forming the carboxylate salt).
• For chromatographic handling: EtOAc/hexanes or DCM/MeOH systems typically provide tunable Rf; acidic modifiers (0.1–1% AcOH) can sharpen bands for acids.

Selection by task (general)

• Cross-coupling at the aryl bromide: 1,4-dioxane, 2-MeTHF, toluene, or DMF commonly used; water co-solvent often beneficial in Suzuki–Miyaura.
• Amidation/esterification: DCM or EtOAc for acid chloride routes; DMF or MeCN for carbodiimide/uronium activations.
• Salt formation or extraction: aqueous NaHCO3/Na2CO3 to form the carboxylate for phase-separable workups; re-acidify with dilute HCl to precipitate the free acid.

Analytical dissolution

• Stock solutions for screening: prepare in dry DMSO or DMF at 10–100 mM, then dilute with reaction medium. Filter through 0.2 µm PTFE if particulates are present.

Note: Always verify actual solubility empirically; the above guidance is based on literature behavior of analogous aryl-ether benzoic acids.

Storage and Reconstitution

Storage (item-specific from product data)

• Store at room temperature.

Additional best practices (general)

• Keep tightly closed in a dry, inert environment; use desiccant if ambient humidity is high to prevent clumping or hydrolysis during long-term storage.
• Protect from prolonged light and heat during storage to minimize any potential degradation of the aryl bromide.
• After opening, consider storing under nitrogen/argon for extended shelf life, especially if frequent opening is expected.

Reconstitution and solution handling (general guidance)

• Prepare concentrated stock solutions in dry DMSO, DMF, or other suitable solvent (e.g., 10–100 mM) for synthetic or analytical use.
• For aqueous work, dissolve in a water-miscible organic solvent first, or convert to a soluble carboxylate salt with dilute base, then adjust to desired medium.
• Filter solutions (0.2 µm PTFE) to remove particulates before use in analytical workflows.

Shipping

• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Shelf life

• Monitor integrity by NMR/HPLC upon receipt and periodically if stored long term. For definitive shelf-life or retest period, refer to the lot-specific CoA.

Structure and Identity

A brominated biaryl ether bearing a benzoic acid: an ortho-(benzyloxyl)benzoic acid with the distal aryl ring brominated at the meta position.

• Product name: 2-[(3-Bromophenyl)methoxy]-benzoic acid (SKU: B708632)
• CAS: 743453-43-2 (product data)
• PubChem CID: 3302765 (product data)
• InChIKey: 429655 (product data; note: truncated/abbreviated as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C14H11BrO3 (computed from name; literature/structure-derived)
• Molecular weight: ~307.14 g/mol (computed from formula; literature/structure-derived)

Structural features (descriptive 2D):

• Core scaffold: a benzoic acid ring with the carboxyl group at position 1 and an O–CH2–Ar substituent at position 2 (ortho).
• Ether linkage: phenoxy oxygen bound to a benzylic methylene (–O–CH2–) that connects to a second phenyl ring.
• Distal aryl ring: a phenyl bearing bromine at the 3-position relative to the benzylic carbon (meta-bromo).
• Functional groups: carboxylic acid (–CO2H), aryl ether (Ar–O–CH2–Ar′), aryl bromide (Ar′–Br).
• Stereochemistry: achiral, no stereocenters; planar aromatic systems connected by a flexible benzylic ether.

Notes on identifiers:

• Where identifiers are missing in product data (e.g., SMILES), consult the Certificate of Analysis (CoA) or SDS for definitive item-specific identity fields.

Synthetic Utility

Functional group orthogonality makes this compound a useful linchpin in multistep synthesis.

Reactive handles (literature/general)

• Aryl bromide (meta to benzylic ether):
  • Cross-coupling platform for C(sp2)–C(sp2/sp) bond formation (Suzuki, Negishi, Stille, Kumada, Sonogashira) and C–N/C–O couplings (Buchwald–Hartwig, Ullmann-type under Cu).
  • Radical-mediated substitutions (e.g., photoredox/nickel dual catalysis) for C–C/C–heteroatom formation under mild conditions.
• Carboxylic acid:
  • Activation to acyl chlorides/anhydrides; amide/ester formation via carbodiimide or uronium reagents; decarboxylative cross-couplings as alternative C–C construction.
• Ether linkage:
  • Typically stable; can serve as a spacer controlling conformation and electronics. Under strong Lewis acids, benzylic cleavage is possible but generally avoided.

Retrosynthetic value

• Enables convergent assembly: diversification of the distal aryl via coupling late in the route while independently varying the amide/ester at the acid terminus.
• Protecting-group strategies: temporary masking of the acid (methyl/benzyl esters) facilitates base-sensitive transformations and improves chromatographic behavior.

Practical notes

• For cross-couplings, optimize ligand/base to balance reactivity with the acidic proton; aqueous base systems (e.g., K3PO4/H2O in dioxane) often mitigate acid–base incompatibilities.
• Preforming the carboxylate salt can improve solubility and reduce acid-induced catalyst inhibition in some cases.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target, or oligonucleotide). No antigen/epitope, clone, isotype, or species reactivity information applies.