Cyclohexyl 5-bromo-2-hydroxybenzoate - ≥95% , CAS No.1131587-74-0

CAS: 1131587-74-0 Cat. No.: C989126 Formula: C₁₃H₁₅BrO₃ Peso molecolare: 299.160

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1CCC(CC1)OC(=O)C2=C(C=CC(=C2)Br)O
• IUPAC Name: cyclohexyl 5-bromo-2-hydroxybenzoate
• InChIKey: YRBDFCPARYWPLJ-UHFFFAOYSA-N
• INCHI: 1S/C13H15BrO3/c14-9-6-7-12(15)11(8-9)13(16)17-10-4-2-1-3-5-10/h6-8,10,15H,1-5H2
• Peso molecolare: 299.160

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Benzoic acid esters
          • Level6 o-Hydroxybenzoic acid esters

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Benzoic acid esters
• Direct Parent: o-Hydroxybenzoic acid esters
• Alternative Parents: Salicylic acid and derivatives 3-halobenzoic acids and derivatives P-bromophenols Benzoyl derivatives Bromobenzenes 1-hydroxy-2-unsubstituted benzenoids Aryl bromides Vinylogous acids Carboxylic acid esters Organooxygen compounds Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: O-hydroxybenzoic acid ester - Halobenzoic acid or derivatives - 3-halobenzoic acid or derivatives - Salicylic acid or derivatives - Benzoyl - 4-bromophenol - 4-halophenol - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Vinylogous acid - Carboxylic acid ester - Carboxylic acid derivative - Organobromide - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organohalogen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy 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

Proprietà chimiche e fisiche

• Peso molecolare: 299.160 g/mol
• XLogP3: 5.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 298.02 Da
• Monoisotopic Mass: 298.02 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 263.000
• 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

No assay-specific protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule building block. For synthetic applications, see the Reaction Conditions section. For use as a substrate/intermediate, follow standard organic synthesis and purification practices (dry/inert techniques for air/moisture-sensitive steps, chromatographic purification, and spectroscopic verification).

Biological Roles

• Item-specific biological data: Not specified for this item; refer to literature if needed.
• General context (no clinical/therapeutic claims)
  • The molecule is a synthetic salicylate derivative featuring a phenolic OH and an aryl bromide. It is not known as a natural metabolite.
  • Salicylate motifs (2-hydroxybenzoates) are prevalent in natural products and metal-chelating ligands due to the ortho-hydroxy–carbonyl arrangement that can form six-membered chelates with many metal ions. This intramolecular H-bonding also modulates acidity and lipophilicity.
  • As a research building block, derivatives may be explored in biochemical probe development or as intermediates toward ligands for metalloenzymes or coordination complexes; however, any biological evaluation is project-specific and outside the scope of this listing.
  • The cyclohexyl ester increases hydrophobicity versus the parent acid, potentially improving membrane partitioning for probe delivery in cell-based studies; such use requires dedicated optimization and safety assessment.

Buffer Applications

This compound is not a buffering agent and lacks a conjugate acid/base pair suitable for maintaining pH in aqueous systems. It is poorly water-soluble and is not typically used to prepare biochemical buffers. For aqueous experimental contexts, dissolve in a miscible organic co-solvent (e.g., DMSO) before dilution if absolutely necessary, or select a true buffer system appropriate to the pH range of interest (e.g., phosphate, Tris, HEPES).

Green Alternatives

Greener choices focus on solvent and catalyst systems rather than on the substrate itself.

• Solvent substitutions (literature guidance)
  • Replace dichloromethane/chloroform with ethyl acetate or dimethyl carbonate for dissolution and workups when feasible.
  • Substitute THF with 2-MeTHF or CPME in cross-couplings and O-alkylations; these offer lower peroxide concerns and preferable life-cycle metrics.
  • Use aqueous micellar media (e.g., TPGS-750-M) for Pd-catalyzed Suzuki couplings at room temperature when boron partners and bases are compatible.
• Catalyst/conditions
  • Employ ligand-optimized Pd systems that operate at lower loadings (≤0.1–0.5 mol%) and in water-rich media to reduce metal and solvent footprints.
  • Consider nickel catalysis for certain couplings to reduce reliance on Pd; balance against substrate sensitivity and selectivity.
• Comparison snapshot (general)
  • DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; may require higher volumes due to solubility differences.
  • THF vs 2-MeTHF: 2-MeTHF derived from renewables, better partitioning for extractions; note higher boiling point and potential for phase behavior differences.
  • DMF/DMAc vs Cyrene or PC (propylene carbonate): greener polar aprotics; verify substrate solubility and base compatibility.
• Trade-offs
  • Greener solvents can alter rates/selectivity; small-scale scouting is recommended. Ensure downstream analytics (e.g., residual solvent specs) align with project requirements.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.
• General notes (no therapeutic claims)
  • As an aryl salicylate bearing an aryl bromide, this compound is best viewed as a synthetic intermediate for discovery and process chemistry rather than as an excipient or formulated component.
  • Potential roles in pharmaceutical R&D include:
    • Scaffold for SAR exploration around salicylate motifs, with C5 diversification via cross-coupling.
    • Protected form of 5-bromo-2-hydroxybenzoic acid, where the cyclohexyl ester can be removed under controlled saponification to unveil the acid late in a sequence.
    • Precursor to ligand frameworks (e.g., salicylaldimine-type ligands after formylation and condensation), useful in asymmetric catalysis development.
  • Any use in GMP or clinical manufacturing would require full qualification (impurity profile, residual solvents, elemental impurities) and adherence to ICH guidelines; no such claims are made for this catalog item.

Physical Properties

• Item-specific specifications
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
  • UV cutoff, residual metals, water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed (reference values; not product specifications)
  • Molecular weight: ~299.16 g/mol (computed from C13H15BrO3)
  • Expected physical state: crystalline solid or low-melting solid (typical for aryl salicylate esters with Br); exact MP not located in common databases.
  • Boiling point: Not readily reported; thermal decomposition likely precedes boiling under ambient pressure for many aryl esters (literature generality).
  • Density: Not located.
  • LogP: Likely moderate to high lipophilicity due to cyclohexyl ester and aryl bromide; quantitative value not located.
  • Solubility: Poorly soluble in water (expected for aryl esters); soluble in common organic solvents such as dichloromethane, chloroform, ethyl acetate, THF, acetone; sparingly to moderately soluble in alcohols. Exact solubilities not located.
  • Acid-base properties: Contains a phenolic OH (weakly acidic; pKa typically ~9–11 for salicylates, literature generality). The carboxyl functionality is esterified (non-ionizable under neutral conditions).
  • Spectroscopic notes (literature expectations): IR ν≈ 1735–1715 cm−1 (ester C=O), 3200–3600 cm−1 (phenolic O–H, often intramolecularly H-bonded in salicylates), aromatic C–H stretches ~3050 cm−1, Ar–Br absorptions in fingerprint region. Distinct 1H NMR phenolic OH often downfield (δ 10–12) due to intramolecular H-bonding; aryl proton pattern consistent with 1,2,5-trisubstitution.

Quality and Grades

• Item-specific quality information
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grades (general guidance)
  • Research-grade small-molecule building blocks are typically provided at high chemical purity sufficient for synthetic and analytical work. When a specific assay purity (e.g., ≥98%) or chromatographic purity is stated on the CoA, it reflects validated analytical methods (commonly HPLC/GC/1H NMR).
  • If an “HPLC-grade” or “chromatography-grade” solvent designation appears (not applicable here unless supplied as a solution), it implies minimized UV-absorbing impurities and low residue on evaporation.
  • Absence/presence of stabilizers: Phenolic salicylate esters generally do not require radical inhibitors; if any stabilizer is used, it will be listed on the CoA. Use of stabilizers may influence downstream polymerization or radical chemistry.
• Batch-specific documentation
  • For exact purity, residual solvents, metal content, and analytical spectra (1H/13C NMR, LC-MS, IR), consult the batch CoA/Spec Sheet. These documents also define acceptance criteria, analytical methods, and storage/handling notes specific to the lot you receive.

Reaction and Applications

As a 5-brominated salicylate ester, this molecule is a versatile bifunctional building block offering orthogonal reactivity at the aryl bromide, the phenolic OH, and the ester linkage.

• Aryl bromide transformations (literature)
  • Suzuki–Miyaura coupling: introduction of (hetero)aryl or vinyl groups at C5 using Pd catalysts (e.g., Pd(PPh3)4 or Pd-PEPPSI variants) with bases such as K2CO3, K3PO4, or Cs2CO3 in dioxane/H2O or toluene/H2O.
  • Buchwald–Hartwig amination: installation of anilines/anilides at C5 using Pd2(dba)3 or Pd(OAc)2 with BINAP/XPhos/BrettPhos ligands; bases such as NaOtBu in toluene or dioxane.
  • Direct lithiation/Br–Li exchange: i-PrMgCl•LiCl (Turbo Grignard) or n-BuLi at low temperature to form arylmetals for subsequent electrophile trapping (requires careful control to avoid deprotonation of phenol—protecting the OH as silyl ether or carbonate is beneficial).
• Phenolic OH transformations
  • Selective O-alkylation/acylation to modulate electronics/solubility; carbonate or silyl protection (TBS/TIPS) to guide site-selective metalation or cross-coupling.
  • Intramolecular H-bonding typical of salicylates can influence acidity and rates; bases like K2CO3/Cs2CO3 in acetone/DMF often suffice for O-alkylation.
• Ester linkage utility
  • Cyclohexyl ester functions as a removable protecting group for the carboxylate: saponify under basic aqueous conditions (NaOH, KOH) or transesterify under acid catalysis to access the acid or alternate esters.
• Application contexts
  • Late-stage diversification of salicylate scaffolds for SAR studies.
  • Intermediate toward functional materials or ligands where ortho-hydroxybenzoate chelation is advantageous.

Reaction Conditions

The following are literature-style general conditions suitable for compounds of this class; they are not item-specific specifications.

• Suzuki–Miyaura coupling at C5–Br
  • Catalyst: 1–3 mol% Pd(PPh3)4 or Pd2(dba)3 (1 mol% Pd) with XPhos/SPhos (2–5 mol%).
  • Base: K3PO4 (2–3 equiv) or K2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (4:1) or toluene/H2O; 80–100 °C; 2–12 h.
  • Notes: Protect or neutralize the phenolic OH if it poisons the catalyst; addition of TBAB or phase-transfer agents can accelerate reactions.
• Buchwald–Hartwig amination
  • Catalyst/ligand: Pd(OAc)2 (1–2 mol%) with BrettPhos or DavePhos (2–4 mol%); base NaOtBu (2–3 equiv).
  • Solvent: toluene or dioxane; 80–110 °C; 4–16 h.
  • Notes: Phenol protection (e.g., TBS) can improve yields with hindered amines.
• Br–Li or Br–Mg exchange (electrophile trapping)
  • Reagents: n-BuLi (1.1 equiv) in THF at −78 to −40 °C; or i-PrMgCl•LiCl in THF at −30 to 0 °C.
  • Notes: Phenolic OH should be protected or pre-deprotonated/complexed; quench with CO2, DMF, electrophiles as desired.
• O-alkylation of phenol
  • Base: K2CO3 or Cs2CO3 (1.2–2.0 equiv).
  • Solvent: acetone, MeCN, or DMF; 25–60 °C; 2–8 h.
  • Electrophiles: alkyl halides, sulfate esters.
• Ester hydrolysis (to 5-bromo-2-hydroxybenzoic acid)
  • Conditions: Aqueous NaOH or KOH (1–2 M) in MeOH/H2O or THF/H2O; 25–60 °C; 1–6 h; then acidify to pH ~2.
  • Notes: Maintain temperature control to avoid competing ether cleavage if phenol is protected.

Safety and Handling

• Item-specific hazard data
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements / GHS Classification / Pictograms: Not specified for this item; refer to SDS.
• General laboratory safety guidance (literature/general; not a substitute for SDS)
  • Likely hazards: Irritation to skin, eyes, and respiratory tract is plausible for aryl esters and phenolic compounds. Avoid inhalation of dust and contact with skin/eyes.
  • PPE: Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize exposure to dust/vapors.
  • Incompatibilities: Strong bases (risk of ester saponification); strong acids (acid-catalyzed transesterification/hydrolysis); strong oxidizers; reactive metals for aryl halides under metal–halogen exchange conditions.
  • Thermal/chemical stability: Aromatic esters are generally stable under ambient conditions; avoid prolonged heating in the presence of base or moisture to prevent hydrolysis. No known tendency for peroxide formation (non-ether).
  • First aid overview: If on skin, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and seek medical advice. If inhaled, move to fresh air; if symptoms persist, seek medical attention. If swallowed, rinse mouth—do not induce vomiting; obtain medical attention.
  • Spill/cleanup: Avoid dust generation. Collect solids with minimal dusting; for solutions, absorb with inert material. Dispose of in accordance with local regulations.
  • Always consult the product SDS for authoritative hazard classifications and response measures.

Solvent Selection

This compound is a moderately lipophilic aryl ester with a phenolic OH and an aryl bromide. It is expected to be essentially insoluble in water but soluble in a range of organic solvents.

• Polarity/miscibility (literature/general expectations)
  • Good solubility: dichloromethane, chloroform, ethyl acetate, acetone, THF, toluene, DMF/DMSO.
  • Moderate solubility: alcohols (MeOH, EtOH, i-PrOH) depending on temperature and presence of base.
  • Poor solubility: water and highly nonpolar alkanes (hexanes) unless warmed or with co-solvent.
• Selection by application
  • Cross-coupling at the aryl bromide: dioxane, toluene, THF, or DMAc/DMF are common; addition of water can aid base solubility for Suzuki reactions.
  • O-alkylation or acylation of the phenol: polar aprotic solvents (acetone, acetonitrile, DMF) with mild inorganic base (K2CO3, Cs2CO3) are typical.
  • Hydrolysis/transesterification: alcoholic solvents (MeOH/EtOH) with acid/base catalysis; or aqueous base in THF/MeOH co-solvent.
• Comparison notes
  • Versus highly nonpolar aromatics (toluene), chlorinated solvents (DCM) often give faster dissolution at room temperature.
  • For greener profiles, consider EtOAc or 2-MeTHF instead of DCM/THF where compatible (see Green Alternatives).

Storage and Reconstitution

• Item-specific storage/shipping
  • Storage Conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from incompatible reagents (strong acids/bases, oxidizers).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• General handling recommendations
  • Protect from prolonged exposure to light and moisture to minimize slow hydrolysis of the ester and oxidation of the phenolic function.
  • After opening, consider storing under inert gas with desiccant to extend shelf life, especially in humid environments.
• Preparation of solutions (general guidance)
  • Solvents: Prepare stock solutions in dry organic solvents such as DMSO, DMF, THF, dichloromethane, or ethyl acetate depending on application. For biological testing contexts, DMSO stocks (e.g., 10–100 mM) are common; filter if needed.
  • Stability in solution: Esters can undergo slow hydrolysis in basic or wet media; prepare fresh solutions for moisture/base-sensitive operations. Refrigerated storage of stock solutions can improve stability, but avoid repeated freeze–thaw cycles; aliquot when practical.
• Research Use Note: For research use only (per Product Data).

Structure and Identity

Cyclohexyl 5-bromo-2-hydroxybenzoate is a salicylate-derived aryl bromide bearing a phenolic OH ortho to a benzoate ester and a bromine at the 5-position.

• Item-specific (from Product Data)
  • CAS: 1131587-74-0
  • InChIKey: 444655
  • 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 product specifications)
  • Expected molecular formula (based on name): C13H15BrO3 (computed)
  • Computed molecular weight: ~299.16 g/mol (computed)
  • Core structural features: benzene ring (1,2-disubstituted, salicylate motif), phenolic hydroxyl at C2, benzoate ester at C1 bearing a cyclohexyl group, aryl bromide at C5.
  • Functional groups: aryl bromide (Ar–Br), phenol (Ar–OH), aromatic ester (Ar–CO2–Rcyclohexyl).
  • 2D description: A 1,2-disubstituted benzenoid ring where positions 1 and 2 are an ortho pair; position 1 carries a carbonyl carbon of a benzoate linking to an O–cyclohexyl substituent; position 2 is a phenolic OH; position 5 bears bromine; the cyclohexyl ring is a saturated six-membered ring tethered through oxygen.
• Stereochemistry: None (all centers achiral; cyclohexyl conformational isomers possible but not configurationally stable).

Synthetic Utility

• Orthogonal functional handles
  • Aryl bromide (C5): gateway to diverse C–C/C–N/C–O bonds via Pd/Ni catalysis (Suzuki, Buchwald–Hartwig, Ullmann-type under copper, or direct metalation).
  • Phenolic OH (C2): tunable reactivity; protect as carbonate/ether/silyl to direct downstream steps; enables formation of bidentate motifs (salicylate chelates) after further elaboration.
  • Benzoate ester: cyclohexyl group offers robustness under many coupling conditions yet is cleavable (basic hydrolysis or acid-catalyzed transesterification), functioning as a carboxyl protecting group.
• Strategic roles in synthesis
  • Modular diversification: Install substituents at C5 via cross-coupling, then manipulate the phenolic OH independently to craft libraries of salicylate derivatives.
  • Late-stage functionalization: Br enables site-selective introduction of sensitive fragments (boronates, stannanes, azoles) under mild cross-coupling.
  • Access to heteroatom-rich frameworks: Through ortho-quinone methide chemistry from salicylates (after activation), or via electrophilic formylation/oxidation sequences directed by the phenol.
• Protecting group logic
  • Cyclohexyl esters balance stability and removability; compared to methyl/ethyl esters, they may hydrolyze slightly slower under base but show good resistance under neutral coupling conditions, reducing premature deprotection.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.