This compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
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
369.400 g/mol
XLogP3
3.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
5
Exact Mass
369.076 Da
Monoisotopic Mass
369.076 Da
Topological Polar Surface Area
96.300 Ų
Heavy Atom Count
25
Formal Charge
0
Complexity
443.000
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
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Recensioni
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Application Protocols
No item-specific validated application protocols are provided for this SKU. The following general practices are commonly used for small-molecule library members:
Stock preparation for screening:
Dissolve in DMSO to 10–50 mM; sonicate/warm gently if needed. Filter through 0.22 μm PTFE if particulate persists.
Store aliquots to avoid repeated freeze–thaw; equilibrate to room temperature before opening to prevent condensation.
Assay dilution:
Titrate into assay buffers to a final DMSO content typically ≤0.5–1.0% v/v. Mix thoroughly to avoid precipitation.
Analytical confirmation:
Verify identity/purity by LC–MS and HPLC prior to key experiments. For oxidative sensitivity studies, include standards of sulfide/sulfoxide/sulfone if available.
For synthesis workflows, see the Reaction Conditions and Synthetic Utility sections. Always adapt procedures to your instrumentation, scale, and safety requirements.
Biological Roles
Item-specific biological data are not provided for this SKU. The following comments are general to benzimidazole–pyridine thioether/sulfoxide scaffolds and are intended strictly for research context (no clinical claims).
Chemical biology context (literature/general):
The lansoprazole scaffold, particularly in its sulfoxide state, is a well-known chemotype for acid-activated covalent modifiers in gastric parietal cells; the sulfide is a reduced analog useful in mechanistic and metabolism studies.
Phenolic substitution at the 4-position can modulate ionization, permeability, and metabolic stability, making hydroxy derivatives valuable for SAR and as intermediates to ether pro-analogs.
In enzymology and ADME research, sulfide/sulfoxide/sulfone series are used to probe oxidative metabolism (e.g., CYP-mediated transformations) and to assign MS/MS fragmentation pathways.
Screening libraries:
As a heteroaromatic, H-bonding small molecule, the compound may be included in targeted libraries exploring benzimidazole recognition motifs.
No target engagement, potency, or selectivity data are specified for this item; consult primary literature and generate experimental data under your assay conditions.
Buffer Applications
This is not a buffering reagent and is not typically used to prepare pH buffer systems. For aqueous assay work, it may be dissolved first in DMSO or another compatible co-solvent and then diluted into a pre-formed buffer (e.g., phosphate, HEPES) at low final organic content (commonly ≤1%). If you require buffering guidance, refer to dedicated buffers such as PBS, HEPES, MOPS, or citrate depending on your pH range.
Green Alternatives
When working with benzimidazole–thioether scaffolds, greener choices can reduce environmental impact without sacrificing performance.
Solvents (general guidance):
Replace DMF/DMAc/NMP with acetonitrile, ethanol, isopropanol, 2-MeTHF, CPME, propylene carbonate where feasible.
For extractions and chromatography, consider EtOAc, 2-MeTHF, or Me-THF/hexanes in place of DCM/CHCl3.
Oxidations to sulfoxide/sulfone (class-relevant):
Use aqueous H2O2–urea (UHP), Oxone (KHSO5), or H2O2 in MeOH/AcOH as alternatives to chlorinated peracids.
Employ phase-transfer catalysis or buffered media to minimize byproducts and waste.
Deprotection/alkylation steps:
Favor carbonate bases (K2CO3, Cs2CO3) in greener solvents (MeCN, acetone, 2-MeTHF) for O-alkylations.
Consider microwave or flow to shorten cycle times and reduce solvent volumes.
Comparison snapshot (literature/general):
m-CPBA in DCM vs UHP/H2O2 in MeOH/H2O
Safety: Peracids are shock-sensitive/irritant; H2O2 systems are generally safer to handle.
Waste: DCM/peracid generates chlorinated waste; aqueous peroxide systems simplify workup.
Selectivity: Peracids often give clean sulfoxidation; peroxide systems may need tighter control of equivalents/time.
Item-specific green data (E-factors, LCA, solvent preferences) are not specified for this item; adapt based on process constraints.
Pharmaceutical Uses
No pharmacopeial or excipient designation is specified for this item. The following reflects general practice for this scaffold family in a research/manufacturing context (no therapeutic claims):
Reference/impurity standard: 4-Hydroxy lansoprazole sulfide can serve as a process or degradation-related reference in analytical methods supporting development of lansoprazole analogs.
Synthetic intermediate: The sulfide state is routinely advanced to sulfoxide in late-stage synthesis; the 4-hydroxy handle enables ether diversification for property optimization.
Analytical development: Useful for method robustness checks (e.g., orthogonal RP–HPLC methods to resolve sulfide/sulfoxide/sulfone), impurity mapping, and forced-oxidation studies.
Any claims of suitability for human or veterinary use are not applicable; this product is provided strictly for research use only, as stated in the Product Data.
Physical Properties
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting point (spec): Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (spec): Not applicable for a high–boiling, likely decomposing heteroaromatic; specific value not specified for this item; refer to CoA/Spec Sheet.
Density (spec): Not specified for this item; refer to CoA/Spec Sheet.
Refractive index (spec): Not applicable/Not specified for this item; refer to CoA/Spec Sheet.
UV cutoff/ε (spec): Not specified for this item; refer to CoA/Spec Sheet.
Water content, residual metals, or impurity limits (spec): Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for this chemical class (benzimidazole–aryl thioethers):
Physical state: Typically off-white to light-colored solid; may exhibit light sensitivity due to thioether and heteroaryl chromophores.
Solubility profile: Poorly soluble in water; soluble in polar aprotic organic solvents (DMSO, DMF, NMP) and moderately in EtOAc/MeOH/ACN; solubility enhanced by the phenolic OH in basic media (phenolate formation).
Acid–base: Benzimidazole is weakly basic (pKa of conjugate acid ~5.5–6.5, literature range for benzimidazoles); phenolic OH pKa typically ~9–11 (literature), enabling salt formation or ionization under basic conditions.
Lipophilicity: Moderate to high logP is typical for lansoprazole analog sulfides; precise value not specified for this item.
All definitive specifications should be confirmed against the CoA/SDS for this SKU.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Context and guidance:
In discovery chemistry and library supply, materials are often provided at research grade with purity verified by HPLC/UPLC and identity confirmed by NMR/MS. If this product is designated with a specific grade on your CoA (e.g., ≥95% HPLC or analytical standard), that denotes:
HPLC area% purity: Suitable for SAR screening and most synthetic applications; specific chromophore content and low UV background are typical.
Analytical/Reference standard: Tighter identity and purity criteria, often with traceable documentation.
Stabilizers/additives: None specified for this item. If present, stabilizers would be disclosed on the CoA/SDS and can affect applications (e.g., UV detection, bioassays).
Documentation: For batch-specific details (purity, analytical methods, residual solvents, water content, counterions), consult the CoA/Spec Sheet linked to the lot number.
Recommendation: If using in sensitive assays (e.g., bioactivity profiling), verify purity by orthogonal methods (HPLC–PDA, HRMS, 1H NMR) and, if necessary, perform a short silica plug or recrystallization to reach the purity required by your protocol.
Reaction and Applications
Use cases for 4-Hydroxy Lansoprazole Sulfide center on its role as a thioether intermediate and heteroaromatic building block within lansoprazole-like scaffolds.
Synthetic transformations (literature/general):
Selective oxidation: Thioether → sulfoxide (PPI-like core) using m-CPBA, Oxone, or H2O2-based systems; further oxidation to sulfone with excess oxidant.
O-alkylation/O-arylation: Phenolic OH enables diversification to ethers/aryl ethers (e.g., K2CO3 or Cs2CO3 in DMF/acetone; Buchwald–Hartwig or Ullmann-type for arylation).
N-functionalization: Benzimidazole N1/N3 alkylation or acylation to tune basicity and solubility (base-promoted in polar aprotics).
Cross-coupling avenues: If a halo substituent is present on the aryl portion (varies by analog), Suzuki/Negishi pathways can append diversity (general to the class).
Research applications:
Probe and standard: Reference material for method development and LC–MS tracking within lansoprazole metabolism/impurity studies (sulfide → sulfoxide/sulfone series).
SAR exploration: Modifying the 4-hydroxy moiety to ether/ester analogs and modulating oxidation state at sulfur supports structure–property profiling.
Practical tips:
Control oxidant equivalents and temperature to stop at sulfoxide where desired.
Protect the phenol (e.g., benzyl or silyl) during aggressive conditions; deprotect under mild hydrogenolysis or fluoride.
Avoid strong acids/oxidants during storage and workup to minimize undesired sulfoxidation or ring opening.
Manufacturer-Provided Applications: Not specified in the Product Data; the above reflect general literature practices for this scaffold class.
Reaction Conditions
General literature conditions suitable for benzimidazole–aryl thioether scaffolds (adjust per substrate and scale):
Thioether → sulfoxide oxidation:
m-CPBA (1.0–1.2 eq) in DCM at 0–25 °C, 0.5–3 h; monitor by TLC/HPLC. Quench with Na2S2O3 to remove excess peracid. Avoid >1.2 eq to limit sulfone.
Urea–H2O2 (UHP, 1.1–1.5 eq) or 30% H2O2 (1.1–1.5 eq) in MeOH/AcOH or MeCN/H2O at 0–25 °C; longer times (2–16 h), good selectivity under buffered conditions.
Sulfoxide → sulfone:
m-CPBA (2.0–3.0 eq) or Oxone (2–3 eq), typically in DCM/MeOH/H2O, 0–25 °C, 2–12 h.
O-alkylation of 4-hydroxy group:
K2CO3 or Cs2CO3 (2–3 eq), alkyl halide (1.2–1.5 eq) in DMF/MeCN/acetone, 20–60 °C, 1–12 h; phase-transfer (TBAB) in acetone can accelerate.
For challenging alkylations, NaH (60% in oil) in DMF/THF at 0–25 °C then add electrophile; rigorously exclude moisture.
N-alkylation on benzimidazole:
Cs2CO3 (2 eq) in DMF/MeCN, 50–80 °C, 2–16 h with benzyl/alkyl halides; control mono- vs di-alkylation by stoichiometry.
Chromatography/workup tips:
Avoid strong acids during workup to limit sulfoxidation. Include antioxidants or use degassed solvents if sensitivity is observed.
Reverse-phase prep-HPLC (MeCN/H2O + 0.1% formic acid or ammonium bicarbonate) can separate oxidation states cleanly.
All parameters above are general literature guidance; optimize for this substrate. Item-specific method details are not specified for this product.
Safety and Handling
GHS classification (item-specific): Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms (item-specific): Not specified for this item; refer to SDS.
General safety guidance for benzimidazole–thioether research compounds (literature/practice):
Hazards: May cause irritation to skin, eyes, and respiratory tract. Thioethers can be malodorous and may oxidize to sulfoxide/sulfone; avoid prolonged air/oxidant exposure.
PPE: Lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to avoid dust/vapor exposure.
Handling: Avoid inhalation of dust. Minimize exposure to heat and light. Keep container tightly closed. Use clean, dry tools to prevent contamination.
Incompatibilities: Strong oxidizers (can oxidize the sulfide), strong acids/bases (may cause degradation/alkylation or salt formation), and electrophiles capable of sulfenylation side reactions.
First aid (overview):
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill response: Avoid dust generation; collect with inert absorbent; dispose per institutional and local regulations.
Always consult the product-specific SDS for authoritative hazard and response information.
Solvent Selection
This compound is a heteroaromatic thioether with a benzimidazole nucleus and a phenolic OH (inferred from name). It behaves as a moderately polar, largely organic-soluble small molecule.
Polarity and miscibility (literature/general for this class):
Water: Low intrinsic solubility at neutral pH; solubility increases in basic aqueous media (phenolate formation) or with co-solvents/surfactants.
Polar aprotic: High solubility in DMSO, DMF, NMP, DMAc, acetonitrile; commonly used for stock solutions (e.g., 10–50 mM in DMSO for screening).
Moderately polar protic: Methanol, ethanol, isopropanol often dissolve at useful concentrations.
Less polar organics: Ethyl acetate, dichloromethane, MTBE, and toluene may dissolve depending on substitution; warming and sonication help.
Practical choices:
Analytical stocks: DMSO for bioassay plates; dilute into assay buffer with ≤1% DMSO final.
Synthesis/processing: DMF/MeCN for alkylation and coupling; DCM/EtOAc for workups and chromatography; MeOH/MeCN–water for HPLC.
pH control: Deprotonation of the phenolic OH (e.g., Na2CO3, K2CO3) improves solubility/reactivity in O-alkylation.
Comparison (general):
DMSO (maximal solubility, high boiling) vs MeCN (lower solubility, easier removal). Choose based on downstream needs (evaporation, assay compatibility).
Item-specific solubility and solvent recommendations are not specified for this item; verify empirically or consult the CoA.
Storage and Reconstitution
Storage conditions (item-specific from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Best practices (general for this scaffold):
Container: Store in a tightly sealed, chemically compatible vial; amber glass recommended to minimize light exposure.
Environment: Keep dry; use a desiccator if possible. Limit exposure to air/oxidants to reduce inadvertent sulfoxidation during long storage.
Stability: Thioethers can slowly oxidize; if long-term storage is planned, consider inert atmosphere (nitrogen/argon) and include oxidation controls in QC.
Reconstitution guidance (general):
Prepare stock solutions in DMSO, DMF, or MeCN at desired concentrations (e.g., 10–50 mM). Record solvent, concentration, and date.
For aqueous use, dilute stocks into buffer with vigorous mixing; maintain low final organic content to prevent precipitation.
If sterile solutions are required for cell-free assays, pass through a 0.22 μm PTFE filter. Avoid aqueous storage of phenolate forms unless immediately used.
Always refer to the lot-specific CoA/SDS for definitive storage and handling instructions.
Structure and Identity
Brief overview: 4-Hydroxy Lansoprazole Sulfide is a benzimidazole–pyridine thioether analog within the lansoprazole chemical family, offered for research and small-molecule library use.
Item-specific identifiers (from Product Data):
SKU: H936610
Product Name: 4-Hydroxy Lansoprazole Sulfide
CAS: 131926-95-9
PubChem CID: 71749086
InChIKey: 264554 (as provided)
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 (inferred from name; literature/general):
Core motif: Substituted 1H-benzimidazole linked via a thioether “sulfide” bridge to a substituted pyridine/aryl moiety (the lansoprazole scaffold typically connects benzimidazole to a pyridine ring through –S–CH2–).
4-Hydroxy substitution: The term “4-hydroxy” indicates a phenolic OH on the heteroaryl/aryl ring (position-4 relative to the benzylic sulfur linkage) in place of an ether substituent seen in lansoprazole.
Stereochemistry: None expected at sulfur in the sulfide state (achiral); sulfoxidation would introduce a stereogenic sulfur, but this item is the sulfide (pre-oxidized) form.
2D description (general): A benzimidazole ring fused to a benzene ring is connected through a benzylic–thioether linker to a 4-hydroxyl-substituted pyridine/aryl ring.
Synthetic Utility
Key functional elements and their reactivity enable diverse transformations:
Thioether (sulfide) linker:
Oxidizable to sulfoxide (chiral S) or sulfone; the oxidation state controls electronics and polarity across the scaffold.
Can undergo electrophilic activation (e.g., sulfenyl chloride formation) facilitating further C–S bond transformations (applied cautiously to avoid over-reaction).
Phenolic OH (4-position):
O-alkylation with alkyl halides/mesylates under basic conditions (K2CO3/Cs2CO3 in DMF/MeCN/acetone) to install ethers.
O-acylation (acyl chlorides/anhydrides; DMAP catalysis) to tune lipophilicity and stability.
Cross-coupling via aryl-O → aryl–C is possible after conversion to a triflate, enabling Suzuki/Negishi/Stille on the derived aryl–OTf.
Benzimidazole nucleus:
N-alkylation/acylation adjusts pKa and solubility; can be protected (e.g., Boc on benzimidazole N, or temporary N-oxide on pyridine analogs in related scaffolds) to direct chemo-selectivity.
Retrosynthetic value:
Modular assembly from benzimidazole and 4-substituted pyridine/aryl building blocks via thioether linkage formation (e.g., S-alkylation of thiols with benzylic halides), then late-stage oxidation and O-functionalization for library generation.
These utilities make the compound a versatile node for diversification in PPI-related chemotypes and beyond.
Target Specificity
Not applicable. This product is a small-molecule research chemical, not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity is specified for this item. For potential biochemical targets in your assays, generate empirical data or consult the primary literature for benzimidazole-based chemotypes.
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