LCL 161, phenol - ≥95%(HPLC) , CAS No.2095244-42-9

CAS: 2095244-42-9 Cat. No.: L287357 Formula: C₃₁H₄₂N₄O₆S Peso molecolare: 598.76 PubChem CID: 138911355

QUALITÀ & PUREZZA ≥95%(HPLC)

Synonyms

tert-Butyl ((S)-1-(((S)-1-cyclohexyl-2-((S)-2-(4-(3-hydroxybenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifiche

Sinonimi

tert-Butyl ((S)-1-(((S)-1-cyclohexyl-2-((S)-2-(4-(3-hydroxybenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

Specifiche e purezza

≥95%(HPLC)

Meccanismi biochimici e fisiologici

Functionalized IAP (XIAP and cIAP) ligand for PROTAC®research and development. Boc protected LCL 161. Supplied with a phenol functional handle for ready conjugation to a linker/target protein ligand. Part of a range of functionalized tool molecules for PR

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥95%(HPLC)

Nomi e identificatori

Sorrisi canonici

CC(C(=O)NC(C1CCCCC1)C(=O)N2CCCC2C3=NC(=CS3)C(=O)C4=CC(=CC=C4)O)N(C)C(=O)OC(C)(C)C

IUPAC Name

tert-butyl N-[(2S)-1-[[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(3-hydroxybenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

InChIKey

SPXBMEKMIPOEMC-LQGLAIQGSA-N

INCHI

1S/C31H42N4O6S/c1-19(34(5)30(40)41-31(2,3)4)27(38)33-25(20-11-7-6-8-12-20)29(39)35-16-10-15-24(35)28-32-23(18-42-28)26(37)21-13-9-14-22(36)17-21/h9,13-14,17-20,24-25,36H,6-8,10-12,15-16H2,1-5H3,(H,33,38)/t19-,24-,25-/m0/s1

PubChem CID

138911355

Peso molecolare

598.76

Application Protocols

The Product Data do not list tested applications or validated protocols for this item. Accordingly, no item-verified procedures are provided here.

General handling suggestions (non-validated; for planning only)

• Prepare a concentrated stock solution in a suitable solvent (commonly anhydrous DMSO) under inert atmosphere if the compound appears air/moisture sensitive. Filter (0.22 μm PTFE) if particulate persists.
• For biochemical assays, dilute the stock into assay buffer with vigorous mixing; keep final DMSO ≤0.5–1% v/v unless your assay tolerates more. Verify absence of precipitation visually and by UV/UPLC.
• For chemical reactions, dry glassware and solvents; consider running a small-scale scout reaction (≤0.05 mmol) to establish solubility and base/catalyst compatibility.

Please treat these as generic planning notes only; implement SOPs validated in your laboratory and refer to the item’s CoA/SDS for definitive instructions.

Biological Roles

Item-specific biological target/role information is not provided in the Product Data. No medical or clinical use is implied; this product is for research use only.

General literature context for phenolic small molecules (not specific to this item):

• Phenolic motifs are widespread in natural products and synthetic ligands, contributing to hydrogen-bonding with proteins (as H-bond donors/acceptors) and modulating redox behavior.
• Ionization state (phenol vs phenolate) can influence membrane permeability, target engagement, and aggregation; buffer pH relative to the compound’s pKa is critical in assay design.
• Phenols may undergo metabolic conjugation (glucuronidation, sulfation) in biological systems, affecting clearance in vivo; in cell-based work this translates to potential phase II metabolism by expressed enzymes.
• Assay considerations: phenols can show nonspecific redox cycling or metal chelation under certain conditions; include appropriate counterscreens and chelator controls to avoid false positives.

Because “LCL 161, phenol” lacks item-specific mechanistic annotation here, users should consult primary literature and the CoA/SDS for any additional information tied to CAS 2095244-42-9 before designing biological experiments.

Buffer Applications

This product is a small-molecule research compound and is not a buffering reagent. No buffer capacity, pKa specifications, or validated buffer formulations are provided for this item.

Practical note (general):

• If the compound must be introduced into an aqueous buffer for assays, prepare a concentrated co-solvent stock (commonly in DMSO or ethanol), then dilute into the target buffer with vigorous mixing to avoid precipitation. Keep the final organic solvent fraction low (often ≤0.5–1% v/v) and verify solubility empirically.

Green Alternatives

While this item is a solid research compound rather than a solvent or reagent in bulk, greener choices can be made in transformations involving phenolic substrates. The following suggestions are literature-based, not item-specific.

• Greener solvents and media

  • Replace DMF/DMAc/NMP with MeCN, 2-MeTHF, CPME, or propylene carbonate where feasible; consider water/ethanol mixtures for EAS or oxidation when compatible.
  • For stock solutions, ethanol or PEG-400 can partially substitute DMSO in some bioassays (validate assay performance).

• Greener reagents and methods

  • O-Alkylation: Use dimethyl carbonate or diethyl carbonate (as alkylating agents and green solvents) under base and elevated temperature in place of alkyl halides.
  • Esterification: Employ EDC·HCl or CDI in greener solvents (EtOAc/2-MeTHF) or use enzymatic acylations.
  • Oxidations: TEMPO/bleach or O2 with catalytic systems instead of stoichiometric Cr(VI)/Mn(VII) reagents when substrate permits.
  • Cross-couplings: Consider micellar catalysis (e.g., TPGS-750-M) or aqueous ethanol with ligand-enabled Pd/Ni catalysts to reduce organic solvent usage.

• Comparative overview (general)

  • Traditional: DMF + alkyl halide (efficient, but reproductive-tox concerns; halogenated waste).
  • Greener: Propylene carbonate + dimethyl carbonate (lower toxicity, recyclable, reduced halogenated byproducts).

• Operational considerations

  • Evaluate life-cycle impacts: solvent volume reduction, recovery/recycling, and minimizing protecting-group steps often deliver the largest green gains.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation-grade designation is provided for this item. This product is supplied strictly for research use only; no therapeutic claims are made or implied.

General R&D context (literature/generic):

• Phenol-containing small molecules are frequently explored in discovery screening as tool compounds due to their capacity for hydrogen bonding and tunable acidity.
• For in vitro studies, researchers often prepare DMSO stock solutions and dilute into assay media while monitoring for precipitation and nonspecific adsorption to plastics.
• Preformulation screening typically evaluates solubility across pH, co-solvent tolerance, and stability (oxidation to quinones, light sensitivity), but such data are item- and lot-specific; consult your internal development protocols and confirm with the item’s CoA.

Physical Properties

Item-specific physicochemical specifications are not listed in the Product Data. Values below are therefore not provided here.

• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.

General chemistry notes (literature/generic guidance, not item-specific):

• Phenols are weak acids (typical phenolic pKa ~9–10), with acidity modulated by ring substituents (electron-withdrawing groups lower pKa; electron-donating groups raise it).
• Solubility: neutral phenols often show moderate solubility in polar aprotic solvents (e.g., DMSO, DMF, acetonitrile) and alcohols; deprotonated phenolates are water-soluble as their salts.
• Solid state: many substituted phenols are crystalline solids with hydrogen-bonding propensity (self-association can affect apparent solubility and dissolution rate).
• Spectroscopy: phenolic O–H stretching typically appears broad around 3200–3600 cm⁻¹ (IR), and phenolic protons often resonate downfield (δ ~8–11 ppm) in 1H NMR due to hydrogen bonding. These are general tendencies; consult the item’s CoA/SDS for definitive data.

Quality and Grades

• Item-specific grade/purity (Product Data)

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

• How to interpret unspecified grade

  • When a catalog entry does not state a formal grade (e.g., AR, HPLC, BioUltra), quality is established by the accompanying Certificate of Analysis (CoA), which details assay, identity confirmation (NMR/LC–MS/HRMS/IR), and impurity profiling.
  • For screening-library compounds, vendors typically provide identity confirmation (≥95% by LC–MS/UPLC and 1H NMR) and report purity by HPLC/UPLC at a specific wavelength. Because such criteria vary, consult the CoA for this lot.

• Stabilizers and additives

  • No stabilizers or inhibitors are listed in the Product Data. If sensitive to oxidation, phenolic solids are often packaged under inert atmosphere or with desiccant; check the label/CoA for any such measures.

• Practical guidance for users

  • Upon receipt, record lot number and request the CoA if not included. Verify purity by an orthogonal method when project-critical (e.g., qNMR, LC–HRMS).
  • If performing UV-based assays or photochemical studies, assess the UV profile/impurities via a blank scan to ensure low background; HPLC-grade solvents and amber vials help maintain consistency.

Reaction and Applications

No Manufacturer Applications were provided for this specific item. The following outlines general reactivity and laboratory applications of phenolic compounds (literature/generic guidance) that may be relevant to phenol-containing small molecules.

• Functional group reactivity

  • Weak acidity enables formation of phenolates, which are potent nucleophiles for O-alkylation (Williamson ether synthesis) and O-acylation (ester formation, carbonates).
  • Electrophilic aromatic substitution (EAS) is activated ortho/para by –OH, enabling nitration, halogenation, sulfonation, and Friedel–Crafts acylation under controlled conditions.
  • Oxidation to quinones (e.g., with Fremy’s salt, CAN) provides redox-active scaffolds.
  • Mitsunobu coupling: conversion to aryl ethers or inversion with alcohol partners under DEAD/DIAD–PPh3 conditions (or greener variants).

• Protecting-group strategies

  • Convert –OH to silyl ethers (TBS/TIPS) or carbonates to guide regioselectivity in metalation or cross-coupling sequences; deprotect under fluoride or mild acid/base as appropriate.

• Cross-coupling pathways

  • Phenol-derived aryl triflates/tosylates/mesylates serve as pseudo-halides for Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig, or Negishi couplings after activating –OH.

• Practical considerations

  • Dry conditions and inert atmosphere improve outcomes for base-mediated transformations.
  • Monitor by TLC/UPLC; phenols often exhibit characteristic UV at 210–280 nm.
  • Workup: neutralize bases, extract into EtOAc/MTBE, and wash with bicarbonate/brine to remove residual phenol or base.

Reaction Conditions

The Product Data do not include reaction parameters specific to this item. The following are general literature conditions for common phenol transformations; optimize for your substrate.

• O-Alkylation (Williamson ether synthesis)

  • Base: K2CO3 or Cs2CO3 (2–3 eq) for benzyl/allyl halides; NaH or t-BuOK for hindered alkyl halides.
  • Solvent: Anhydrous DMF, MeCN, or acetone.
  • Temperature/time: 25–80 °C, 2–16 h. Monitor by TLC/UPLC.

• O-Acylation (ester/carbonate formation)

  • Reagents: Acyl chlorides or anhydrides with pyridine/Et3N; or CDI/DMAP for mild conditions.
  • Solvent: DCM, THF, or 2-MeTHF. 0–25 °C, 0.5–4 h.

• Formation of aryl triflates (activation for cross-coupling)

  • Reagents: Tf2O (1.1–1.5 eq), base (2,6-lutidine or pyridine), −20 to 0 °C in DCM.
  • Subsequent coupling: Pd(0) catalyst (e.g., Pd2(dba)3/XPhos) in toluene/MeCN or dioxane/H2O, 50–100 °C.

• Oxidation to quinones

  • Reagents: Fremy’s salt, CAN, or IBX/DMSO; solvent: MeCN/MeOH/H2O mixtures; 0–25 °C.

• Protecting-group installation

  • Silylation: TBSCl (1.5 eq), imidazole, DMF, 25 °C; deprotect with TBAF (THF) at 0–25 °C.

Notes

• Exclude moisture and oxygen where bases or low-valent metals are employed.
• For scale-up, assess exotherm and gas evolution; neutralize carefully to avoid emulsions.
• Expected yields are substrate-specific; typical ranges 60–90% under optimized conditions (literature/general).

Safety and Handling

Authoritative safety information must be obtained from the SDS. The Product Data for this item does not list specific GHS details.

• GHS/Labeling (Product Data)

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• Storage and shipping (Product Data)

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

• General laboratory precautions for phenolic compounds (literature/generic guidance)

  • Potential hazards: Many phenols are irritants or corrosive to skin/eyes and can be harmful if swallowed or absorbed. Work in a chemical fume hood; avoid inhalation of dust/aerosols.
  • PPE: Lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Change gloves regularly.
  • Handling: Avoid prolonged contact with bases or strong oxidants; phenols can undergo oxidative darkening. Use dry, clean tools; minimize exposure to air and light when possible.
  • First aid (overview; defer to SDS): In case of skin contact, remove contaminated clothing and rinse with water. For eye contact, rinse cautiously with water for several minutes and seek medical attention. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical advice.
  • Waste: Collect phenolic wastes in halogenated/non-halogenated organic solvent waste streams per your institution’s policy. Avoid drain disposal.

Solvent Selection

This item is a small-molecule solid (typical for phenolic derivatives), not a bulk solvent. Solvent choice here refers to dissolving the compound for reactions, screening, or analytics.

• Item-specific solubility data: Not specified for this item; refer to CoA/Spec Sheet.

• General solvent guidance for phenolic compounds (literature/generic)

  • Polar aprotic: DMSO and DMF are common first choices for stock solutions and reactions due to strong solvating power for H-bond donors/acceptors.
  • Protic: Methanol, ethanol, and isopropanol may dissolve many phenols and are amenable to preparative workups and recrystallizations.
  • Partially miscible organics: Ethyl acetate, acetone, and acetonitrile often give workable solubility while supporting a broad range of transformations and analyses.
  • Nonpolar aromatics: Toluene/xylene can be preferred for high-temperature substitutions or dehydrative couplings when the substrate is sufficiently lipophilic.

• Dielectric/polarity context (typical values; literature)

  • DMSO (ε ≈ 47), DMF (ε ≈ 37), MeCN (ε ≈ 37), MeOH (ε ≈ 33) provide good ionization of phenolates; toluene (ε ≈ 2.4) suits neutral, hydrophobic systems.

• Practical tips

  • Prepare concentrated DMSO stocks (e.g., 10–50 mM) then dilute into assay buffers with vigorous mixing to avoid precipitation; include co-solvent ceilings (commonly ≤0.5–1% DMSO in biological assays).
  • For base-promoted O-alkylations/acylations, use anhydrous polar aprotic solvents (DMF/DMSO/MeCN) with inorganic bases; exclude water.

Storage and Reconstitution

• Storage (Product Data)

  • Store at −20 °C.
  • Shipped in ice chest with ice pads to maintain a cold chain.

• Packaging and stability

  • Appearance and stabilizers are not specified for this item; refer to CoA/Spec Sheet.
  • Upon receipt, keep container tightly closed. Minimize freeze–thaw cycles by aliquoting.

• Reconstitution (general guidance; not item-specific)

  • Solvents: Many phenolic small molecules dissolve well in anhydrous DMSO, DMF, ethanol, or methanol. Start with a small test aliquot to determine solubility.
  • Procedure: Warm to room temperature in a desiccator before opening. Add solvent incrementally with gentle vortexing/sonication. If needed, mildly heat (≤40 °C) briefly. Filter through 0.22 μm PTFE if particulates remain.
  • Working stocks: For bioassays, prepare 10–50 mM DMSO stocks and store aliquots at −20 °C in amber vials. Record preparation date and concentration.

• Stability considerations (generic)

  • Protect from light and air to mitigate oxidative discoloration common to phenolic materials.
  • Avoid prolonged exposure to strong bases or oxidants during storage.

Always refer to the product label and SDS/CoA for item-specific stability limits, re-test intervals, and any special precautions.

Structure and Identity

Brief description: LCL 161, phenol is supplied as a small-molecule research chemical in our small-molecule/compound library category. Item-specific identifiers are limited; structural details below reflect only what is provided and general notes.

• Item-specific identifiers (Product Data)

  • SKU: L287357
  • Product Name: LCL 161, phenol
  • CAS: 2095244-42-9
  • PubChem CID: 138911355
  • InChIKey: 342225 (as provided; truncated/atypical format in Product Data)
  • 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.

• Structural features (general chemistry context)

  • Name indicates a phenolic functionality (–Ar–OH). Phenols comprise an aromatic ring directly bearing a hydroxyl group, enabling hydrogen bonding, weak acidity, and electrophilic aromatic substitution chemistry (literature/general knowledge).
  • Typical 2D motif for phenols: a six-membered benzene ring with an –OH substituent; additional substituents (if any) define electronics/sterics (literature/general knowledge).

• Stereochemistry

  • Phenolic cores are typically achiral; chirality (if present) would arise from additional substituents or axial elements. No stereochemical information is provided for this item (Product Data).

Synthetic Utility

From a synthetic standpoint, phenolic functionality provides multiple, orthogonal handles useful in route design (general literature guidance):

• Nucleophilicity after deprotonation: Formation of aryl ethers via Williamson ether synthesis; carbonate and carbamate formation (CDI, Boc2O) for protection or further diversification.
• Traceless activation: Convert –OH to sulfonates (triflate, tosylate, mesylate) enabling C–C/C–N cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Negishi) where direct aryl halides are unavailable.
• Regioselective EAS: Ortho/para activation by –OH permits site-selective nitration/halogenation/acylation; temporary protection can steer regioselectivity and suppress overreaction.
• Oxidation and redox tuning: Access to quinones/catechols enables redox-active intermediates for further annulations and cycloadditions.
• Directed metalation: Phenol (as silyl ether or carbamate) can direct ortho-metalation with strong bases (s-BuLi/TMEDA), unlocking formylation, borylation, or halogen–lithium exchange sequences.

Practical guidance

• Choose protecting groups to survive subsequent steps (e.g., TBS for strong base; benzyl for hydrogenolysis; carbonate for mild acid/base removal).
• In multistep sequences, phenolic –OH can serve as a polarity tag to aid crystallization or chromatographic separation.
• Ensure water control; phenolates are moisture-sensitive in coupling steps and can revert or hydrolyze under acidic workups.

Target Specificity

Target/epitope specificity, binding constants, or enzyme/receptor profiles are not provided in the Product Data for this item. No claims regarding biological targets are made. For any exploratory target engagement studies, please consult primary literature relevant to CAS 2095244-42-9 and verify identity/purity with the product’s CoA before use.

Domande frequenti

What is the purity of this product, and how is it determined?

This product is supplied at ≥95% purity, determined by HPLC. Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 2095244-42-9, the molecular formula is C??H??N?O?S, and the molecular weight is 598.76 g/mol. InChIKey SPXBMEKMIPOEMC-LQGLAIQGSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.