Bisphenol AP-d , CAS No.2469555-57-3

CAS: 2469555-57-3 Cat. No.: B1451754 Formula: C₂₀H₁₃D₅O₂ Molecular Weight: 295.39

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Bisphenol AP-d 5 is the deuterium labeled Bisphenol AP.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Molecular Weight: 295.39

Application Protocols

No item-specific tested applications are provided in the Product Data. As general guidance for analytical use as an internal standard:

• Stock solution preparation (analytical):
  • Prepare a primary stock at 0.5–1.0 mg/mL in LC-MS grade acetonitrile or methanol. Filter if necessary (PTFE, 0.2 µm) to remove particulates.
  • Store aliquots at −20 °C, protected from light. Avoid repeated freeze–thaw cycles.
• Working solutions and spiking:
  • Prepare serial dilutions freshly in mobile phase (e.g., water/MeCN with 0.1% formic acid) or extraction solvent.
  • Spike a constant amount of the deuterated standard into all calibration and sample extracts prior to extraction/cleanup to correct for matrix effects.
• LC-MS/MS setup (example-only, literature-style):
  • Monitor distinct MRM transitions corresponding to the deuterated analogue (mass shift relative to native). Optimize source parameters for phenolic aromatics.

Always verify concentrations, transitions, and stability with your laboratory’s validated methods. For synthesis uses, follow reaction-specific procedures provided in the Reaction Conditions section.

Biological Roles

No item-specific biological data are provided. The following notes describe general biochemical considerations for bisphenolic compounds and deuterated analogues (literature context; not an endorsement of biological use):

• Structural motifs: Bisphenols possess two phenolic OH groups capable of hydrogen bonding and π–π interactions. Their rigid, hydrophobic scaffold enables binding in certain protein hydrophobic pockets in vitro.
• Assay relevance: Deuterated analogues are primarily used as internal standards in bioanalytical quantitation (e.g., LC-MS/MS of bisphenols in plasma/urine extracts, environmental matrices). The deuterium label yields distinct mass transitions while closely matching extraction and ionization behavior of the unlabeled analyte.
• Metabolism (general for bisphenols): Phase II conjugation (glucuronidation/sulfation) of phenolic OH groups is common in biological systems; enzymatic pathways may differ among species. These points matter for analytical method setup (e.g., inclusion of deconjugation steps or targeted detection of conjugates), but do not pertain to this item’s use claims.
• Binding/biorecognition: Phenolic small molecules can interact with certain proteins in biochemical assays; however, no target specificity or bioactivity is claimed or provided for this product.

Important: This product is designated for research use only and is not intended for any diagnostic, therapeutic, or in vivo use.

Buffer Applications

This product is a hydrophobic, phenolic small molecule standard/monomer and is not a buffering agent. It does not serve as a conventional buffer component or pH stabilizer.

Practical notes:

• For preparing analytical standards in aqueous systems, use water-miscible organic cosolvents (e.g., MeCN or MeOH). If higher apparent solubility is required, basic aqueous conditions can generate phenolate salts, but this may not be suitable for all assays and may risk deuterium exchange depending on labeling sites.
• For chromatographic mobile phases, standard buffer systems (ammonium formate/acetate for LC-MS) are employed to control ionization—not the analyte/standard itself.

Green Alternatives

Context: Bisphenol AP-d is a labeled reference/standard or specialty monomeric building block; it is not a solvent. “Greener alternatives” therefore refer to process choices and solvent selection rather than a substitute analyte (analytical methods require the isotopologue of interest).

Greener process considerations (general):

• Solvent choice:
  • Prefer MeCN, EtOH, 2-PrOH, or ethyl acetate over chlorinated solvents where feasible in extractions and standard preparations.
  • For base-promoted etherifications, consider 2-methyltetrahydrofuran (2-MeTHF) or CPME as greener ethers compared to THF/DMF/DMSO when compatible with reactivity.
• Carbonate formation: avoid phosgene; use dimethyl/diphenyl carbonate under catalytic transesterification (e.g., Zn, Ti catalysts) when synthesizing carbonate derivatives for research.
• Waste minimization: isotopic standards are typically used at low concentrations—prepare small batches of working solutions to reduce disposal volumes.

Illustrative comparison (general guidance):

• THF vs 2-MeTHF: 2-MeTHF is bio-based, higher boiling, forms fewer peroxides; may offer similar solvency for phenolic transformations.
• DMF/DMSO vs propylene carbonate: propylene carbonate is less hazardous and high boiling, suitable for some base-mediated reactions; assess downstream removal.

Trade-offs:

• Highly green solvents may alter solubility or reaction rates for phenolic substrates; validate on small scale.
• Analytical LC-MS often mandates MeCN/MeOH/water systems for volatility and ionization performance—these are already relatively benign compared to chlorinated solvents.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this SKU. The product is for research use only.

Relevant non-clinical, laboratory contexts:

• Analytical reference standard: deuterated bisphenols are used as internal standards in quality control testing of materials (e.g., polymer leachables/extractables studies) where sensitive quantitation of bisphenol AP is required.
• Process/packaging studies: supports method development for monitoring residual monomers or migrants in manufacturing environments and packaging systems.

Notes:

• Do not use in human or veterinary applications.
• If integrating into GMP analytical workflows, obtain full CoA with isotopic enrichment, impurity profile, and validated assay methods. Verify stability-indicating methods for stock solutions in approved solvent systems.

Physical Properties

Item-specific specifications were not provided in the Product Data. Values below are general/literature guidance for non-deuterated bisphenol AP (for method development only). Deuteration changes exact molecular weight but typically has negligible effect on bulk phase properties.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (literature, bisphenol AP): typically in the ~160–170 °C range (reports around 162–165 °C are common). Exact MP for the deuterated analogue and this lot is not specified.
• Boiling point: High; compound decomposes before boiling at 1 atm (literature). Not typically distilled.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature trends):
  • Water: very low solubility due to hydrophobic triaryl core.
  • Organic: soluble in polar aprotic and protic organics (MeOH, EtOH, acetone, acetonitrile, DMSO, DMF, THF); limited in aliphatic hydrocarbons.
• pKa (phenolic OH, literature): phenolic pKa typically ~9.5–10.5; exact values for the two OH sites in bisphenol AP vary by medium and ionic strength.
• LogP (literature expectation): high (hydrophobic triaryl structure); reported values for related bisphenols are typically logP > 3.
• Refractive index: Not applicable for a solid; Not specified for this item.

Always verify property data on the lot-specific CoA/SDS before designing purification or analytical methods.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and isotopic enrichment.

Interpretation and guidance (general):

• Deuterated standards: For -d products, two quality dimensions are critical:
  1. Chemical purity (% area by GC/HPLC, residual solvents, inorganic residues).
  2. Isotopic enrichment and labeling pattern (overall %D and location-specific D incorporation), which directly affect mass spectral response and chromatographic coelution behavior.
• Analytical use: Isotopically labeled bisphenols are commonly used as internal standards in LC-MS/MS or GC-MS quantitation of bisphenol residues in polymers, environmental, or food-contact extracts. Verify the exact D count and labeling sites on the CoA to ensure correct mass transitions and to avoid overlap with native or partially deuterated backgrounds.
• Stabilizers/inhibitors: None specified for this item. If stabilizers are present, they will be listed on the CoA; their presence can influence blank levels and UV baselines.
• UV background: If intended for LC-UV, check the CoA for low-UV impurities; bisphenols have strong aromatic absorbance, so solvent and impurity background can matter.

Recommendation: Request recent CoA, SDS, and, if needed, a Spec Sheet detailing isotopic purity, residual solvent limits, and chromatographic suitability (HPLC/LC-MS) for your method.

Reaction and Applications

Focus and use cases:

• Analytical applications (typical for -d materials):

  • Internal standard for LC-MS/GC-MS quantitation of bisphenol AP (native) in polymer extracts, environmental samples, and product testing. Deuterium labeling provides defined mass shifts for MRM/SIM methods and compensates for matrix effects and recovery losses.
  • Method validation: spike-recovery, calibration curve bracketing, and isotopic dilution workflows.

• Synthetic/derivatization chemistry (general for bisphenols; not item-specific):

  • O-alkylation/etherification: phenolic OH can be alkylated using alkyl halides or sulfate esters under basic conditions (e.g., K2CO3/DMF or NaH/THF), forming diaryl aryl-alkyl ethers.
  • Esterification/acylation: acyl chlorides or anhydrides yield aryl esters; useful for protecting phenols or modulating chromatographic behavior.
  • Carbonate formation: reaction with phosgene or safer equivalents (triphosgene, diphenyl or dimethyl carbonate) to afford polycarbonates/oligocarbonates.
  • Epoxy precursor formation: with epichlorohydrin under basic conditions to form diglycidyl ethers (DGE) akin to bisphenol-based epoxy monomers.
  • Electrophilic aromatic substitution: phenolic activation directs ortho/para; however, sterics around para positions are constrained by substitution.

Practical tips:

• For analytical standards, minimize proton–deuteron exchange: avoid strong protic/alkaline media if the labeled positions are at exchangeable sites (pattern not specified—verify on CoA). Use dry, neutral solvents and store cold.
• For O-alkylation, dry conditions and anhydrous bases improve conversion; monitor by TLC/HPLC with UV at 220–280 nm (aromatic bands).
• For carbonate/epoxy chemistry, control base stoichiometry to limit oligomerization/crosslinking.

Reaction Conditions

The following are literature-style general conditions for transformations of bisphenolic substrates; actual conditions should be optimized per substrate and scale. No item-specific specifications are provided.

• O-alkylation (aryl–O–R ether formation):

  • Typical: K2CO3 (2–3 equiv) in DMF or acetone, alkyl halide (1.2–2.0 equiv per OH), 25–60 °C, 2–16 h. Alternatively, NaH (1.1–2.2 equiv) in THF/DMF at 0–25 °C for more hindered electrophiles.
  • Notes: Strictly anhydrous conditions improve yields; monitor by HPLC/LC-MS.

• Esterification (aryl esters):

  • Acyl chloride (2.2 equiv), pyridine or Et3N base, DCM/MeCN, 0–25 °C. Or DCC/DMAP coupling with carboxylic acids in DCM/DMF at 0–25 °C.

• Carbonate formation:

  • With diphenyl carbonate or dimethyl carbonate, catalytic base or transesterification catalyst (e.g., Zn, Ti), 120–180 °C (solvent-free or high-boiling solvent). For small-molecule carbonates, 60–120 °C in MeCN/acetone with suitable activating agents.

• Epoxy monomer (diglycidyl ether) formation:

  • Epichlorohydrin excess, NaOH, 50–90 °C, phase-transfer catalyst optional; purify by vacuum distillation/precipitation.

• Analytical derivatization (GC):

  • Silylation with BSTFA + 1% TMCS, 60–70 °C, 15–30 min, dry acetonitrile or pyridine.

Deuterium label care:

• Use neutral/dry media to reduce H/D exchange risk.
• Avoid prolonged exposure to strong acids/bases or metal-catalyzed hydrogenation conditions if labeling could be labile (site-specific stability depends on labeling pattern; consult CoA/labeling map).

Safety and Handling

Hazard classification details (GHS, H-statements, pictograms) are not provided in the Product Data for this SKU; consult the SDS for authoritative information.

General safety guidance for bisphenolic solids (literature/experience-based):

• Likely hazards: eye/skin irritation; harmful if swallowed; phenolic compounds can be irritant/sensitizers. Avoid dust generation and inhalation.
• PPE: use lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize dust and vapors.
• Incompatibilities: strong oxidizers; strong bases/acids may cause rapid salt formation or decomposition; acylating/alkylating agents react readily with the phenolic OH.
• First aid overview: remove to fresh air after inhalation; flush eyes/skin with water for ≥15 min; remove contaminated clothing; seek medical attention if symptoms persist. If ingested, rinse mouth—do not induce vomiting; obtain medical aid.
• Fire safety: organic combustible solid; use CO2, dry chemical, or foam. Thermal decomposition may release irritating fumes.
• Spill response: avoid dust; collect mechanically or with HEPA-filtered vacuum; place in suitable container for disposal. Decontaminate area with appropriate solvent while observing compatibility.
• Waste: dispose according to local regulations; phenolic wastes may require special handling.

Storage and shipping (item-specific):

• Storage conditions: Store at -20 °C (per Product Data). Keep tightly closed, dry, and protected from light.
• Shipped in: Ice chest + ice pads (per Product Data).

For all safety decisions, defer to the product SDS.

Solvent Selection

Applicability: As a hydrophobic, di-phenolic triarylmethane derivative, Bisphenol AP-d dissolves best in mid- to high-polarity organic solvents. Selection should reflect your downstream application (synthesis vs. analytical standard preparation).

General solubility/miscibility guidance (literature/experience):

• Preferred solvents for stock solutions (analytical): acetonitrile (MeCN), methanol, isopropanol, acetone; DMSO/DMF for highly concentrated stocks.
• Less suitable: aliphatic hydrocarbons (hexanes, heptane) due to limited solubility; aqueous media require organic cosolvent or basification to form phenolate salts.
• pH leverage: Deprotonation (e.g., NaOH, K2CO3) forms soluble phenolates in water/MeOH but may trigger side reactions for synthetic applications.

When to choose what:

• LC-MS internal standard stocks: MeCN or MeOH (volatile, MS-friendly). Add ≤0.1% acid (FA/AA) only if compatible with your quantitation strategy; note that protonation state can influence ionization efficiency relative to the native analyte.
• Preparative workup or derivatization: acetone, MeCN, or THF for O-alkylation/acylation steps; DMSO/DMF for SN2 etherifications with weak bases.
• Spectroscopy (UV/fluorescence): MeCN or EtOH provide clean baselines; avoid strongly absorbing stabilizers.

Quick comparison (general):

• MeCN: strong solvency, low viscosity, LC-MS compatible.
• MeOH: protic, aids dissolution; can engage in H-bonding.
• DMSO/DMF: maximal solvency; harder to remove; non-volatile.

Always confirm solvent grade (LC-MS, HPLC, anhydrous) and compatibility with your application.

Storage and Reconstitution

Item-specific storage/shipping (from Product Data):

• Storage conditions: Store at −20 °C.
• Shipped in: Ice chest + ice pads.

General handling guidance:

• Keep container tightly closed under dry, inert atmosphere if possible. Include desiccant to minimize moisture uptake.
• Protect from light and heat. Allow vial to warm in a desiccator to room temperature before opening to prevent condensation.

Reconstitution and solution stability:

• Solvents: LC-MS grade acetonitrile or methanol are recommended for analytical stocks; DMSO/DMF can be used for highly concentrated solutions but are less volatile.
• Concentration: common analytical stocks 0.1–1.0 mg/mL; prepare working dilutions freshly.
• Stability: Specific solution/solid-state stability is not provided for this item; refer to CoA/Spec Sheet. As a general practice, aliquot and store solutions at −20 °C, protected from light, and avoid repeated freeze–thaw cycles.

Notes on deuterated materials:

• If deuterium is located at exchangeable positions, exposure to protic or basic media may induce H/D exchange. Use dry, neutral solvents for long-term stocks and verify mass spectra periodically.

For authoritative guidance, consult the product’s CoA and SDS.

Structure and Identity

Brief description: Bisphenol AP-d is a deuterium-labeled analogue of the industrial monomer bisphenol AP, featuring two para-phenolic groups on an aryl-alkylidene triaryl methane core. Labeling pattern and deuterium content for this SKU are not provided in the Product Data.

• SKU: B1451754
• Product name: Bisphenol AP-d
• CAS: 2469555-57-3
• Category: Life science research reagent (research use only)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature for non-deuterated bisphenol AP):

• Core motif: triarylmethane-type central quaternary carbon bearing one phenyl and two para-hydroxyphenyl groups (p,p′-dihydroxy substitution).
• Functional groups: two phenolic OH groups (acidic, nucleophilic after deprotonation), extended aromatic system (three phenyl rings).
• 2D description: two para-hydroxyphenyl rings linked through a central sp3 carbon, which also carries a phenyl and a methyl substituent (literature depiction of bisphenol AP); the deuterated analogue substitutes one or more hydrogens with deuterium (pattern not specified here).

Notes:

• Exact deuteration sites and isotopic enrichment determine the precise formula and mass; consult the lot-specific CoA.

Synthetic Utility

General reactivity of the bisphenol AP scaffold (applies to unlabeled core; deuteration does not materially change connectivity):

• Functional handles: two phenolic OH groups enable diverse O-functionalizations—etherification, esterification, carbonate formation, and urethane linkage to isocyanates. The triaryl core confers rigidity and hydrophobicity.
• Polymer/oligomer precursors (research scale):
  • Polycarbonates via transesterification with dialkyl/aryl carbonates.
  • Epoxy monomers via reaction with epichlorohydrin (diglycidyl ethers), analogous to other bisphenols.
  • Poly(arylene ether)s by nucleophilic aromatic substitution with activated dihalides (using the phenolate as nucleophile) when appropriately activated partners are used.
• Protecting group chemistry: transient conversion to carbonate, silyl ethers (TBDPS/TBS), or benzoates facilitates selective transformations on the aromatic rings if needed.
• Analytical derivatization: formation of silyl ethers (e.g., BSTFA) or acyl derivatives to enhance GC volatility or modify LC retention for trace analysis of bisphenol AP; the deuterated standard supports isotope-dilution calibration for the same derivatized species.

Caution for deuterated materials:

• Avoid conditions that promote H/D exchange at labeled positions (pattern unknown here). Generally, strong bases, acids, and catalytic hydrogenation can scramble deuterium labels at benzylic or aromatic positions under certain conditions.

Target Specificity

Not applicable. This product is a small-molecule chemical standard/monomer, not a biological targeting reagent (e.g., antibody, ligand with defined receptor specificity for assays). No antigen/epitope or species reactivity is relevant.