This compound belongs to the class of organic compounds known as organophosphine oxides. These are organic compounds containing the phosphine oxide group, with the general formula R3P=O or R3P+O-.
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
169.590 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
169.042 Da
Monoisotopic Mass
169.042 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
114.000
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
2
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No validated bioassay or analytical application protocols are provided in the Product Data for this item.
General handling protocols for synthetic use:
Preparing stock solutions: Dissolve the hydrochloride salt in water, MeOH, or DMSO to prepare screening solutions. Filter through 0.22 µm if particulate is observed.
Free-base generation: Suspend in aqueous NaHCO3/Na2CO3 and extract into EtOAc or DCM; dry and concentrate to obtain the free base for subsequent organic reactions.
31P/1H/13C NMR characterization: Record spectra to confirm identity and salt state; phosphine oxides typically give a characteristic 31P resonance distinct from phosphines.
For any biological protocols (if subsequently developed by the user), design and validate conditions de novo and refer to institutional SOPs.
Biological Roles
Item-specific biological roles: None specified; this product is supplied for research use only.
General context (non-clinical):
Endogenous occurrence: 1,4-Azaphosphinane phosphine oxides are synthetic; they are not known natural metabolites.
Biochemical utility: After derivatization, organophosphorus heterocycles can serve as probes of polarity or H-bonding in biochemical systems due to the strong P=O dipole, but such applications depend on conjugation to biomolecular handles.
Stability: The phosphine oxide is typically resistant to hydrolysis under physiological pH; the ammonium chloride salt can increase aqueous solubility for in vitro assay development or as an intermediate toward bioconjugates.
Important limitation: No medical, diagnostic, or therapeutic use is intended or implied. Any biological testing should be performed under appropriate approvals and with reference to the SDS and institutional biosafety protocols.
Buffer Applications
Not typically used as a buffering agent. This compound is a heterocyclic phosphine oxide supplied as a hydrochloride salt; it does not constitute a defined acid/base conjugate pair with a target pKa range for biological buffers.
Practical note: If aqueous handling is needed, dissolve the HCl salt directly in water or buffer appropriate for your downstream chemistry, or convert to the free base before formulating in organic media. For true buffering needs, select standard systems (e.g., phosphate, HEPES, Tris) suited to your pH range.
Green Alternatives
This item is a solid heterocyclic building block rather than a solvent; green considerations center on choice of reagents and media for its transformations.
Greener tactics (literature-informed):
Reduction of phosphine oxides: Prefer hydrosilane systems that can be recycled (e.g., polymethylhydrosiloxane, PMHS) over stoichiometric chlorosilanes; catalytic hydrogenolysis routes under metal catalysis are emerging.
Solvent choices: Use water/ethanol or 2-MeTHF/EtOAc where feasible for N-derivatizations and coupling reactions; avoid chlorinated solvents unless necessary.
Base selection: For salt liberation, choose carbonate/bicarbonate in water or aqueous ethanol, minimizing strong organic bases and halogenated waste.
Telescoping: Perform in situ free-basing followed by direct coupling to limit isolation steps and solvent usage.
Illustrative comparison (general):
Conventional: Dichloromethane, oxalyl chloride, trichlorosilane for P=O manipulations → higher hazard and corrosive waste.
Greener: 2-MeTHF or EtOAc as media; PMHS or 1,3-diphenyldisiloxane with catalytic Ti or B-based systems; electrochemical or photochemical activation where supported.
Trade-offs:
Greener reductants may require higher temperatures or catalysts and can have slower kinetics.
Ethyl acetate and 2-MeTHF can alter solubility of the HCl salt; free-base conversion may be required.
Note: These are general green chemistry suggestions for the class; adapt to your reaction and consult EHS for waste minimization.
Pharmaceutical Uses
No pharmacopeial or excipient role is specified for this item. It is offered strictly for research and laboratory synthesis.
Salt form: The hydrochloride salt can aid in handling and weighing during discovery-scale synthesis and can enhance solubility in screening solutions for structure–activity relationship (SAR) campaigns, if the scaffold is used as a synthetic intermediate.
Process considerations: If used in route scouting, confirm salt stoichiometry and residual chloride when targeting neutral or non-chloride final forms; implement suitable in-process controls (IPC) such as argentometric titration or ion chromatography.
No therapeutic claims are made. Not for human or veterinary use.
Physical Properties
Item-specific values (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Storage Conditions: Room temperature (per Product Data).
Other specifications (bp, mp, density, solubility, UV cutoff, water/peroxide/metal content): Not specified for this item; refer to CoA/Spec Sheet.
General/literature-based expectations for this class (non-spec):
Physical state: Typically an off-white to white crystalline solid for small heterocyclic phosphine oxide HCl salts.
Solubility: Hydrochloride salts of amine-containing heterocycles are commonly highly soluble in water and polar protic solvents (e.g., MeOH, EtOH); moderate in polar aprotics (DMF, DMSO, MeCN); poor in nonpolar hydrocarbons.
Thermal behavior: Phosphine oxides are thermally robust relative to P(III) analogs; HCl salts may show hygroscopicity and may cake upon moisture uptake.
Acid/base: Exists predominantly as the ammonium chloride salt; free base obtainable by neutralization (e.g., aqueous NaHCO3/Na2CO3), typically increasing solubility in organic solvents.
Note: The above are qualitative, literature-informed characteristics for related compounds and are not product specifications. For precise numerical data (mp, purity assays, residual solvents), consult the CoA/SDS.
Quality and Grades
Item-specific (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
Without a declared grade (e.g., AR, ≥98%, HPLC, BioXtra), end-users should reference the Certificate of Analysis for assay method (qNMR, HPLC/GC), residual solvents, and impurity profile.
For heterocyclic salts used as synthetic building blocks, typical quality determinants include: assay of active species (salt vs. free base content), water content (Karl Fischer), residual inorganic chloride quantitation (ion chromatography), and identity confirmation (1H/13C/31P NMR, HRMS).
If intended for catalysis/ligand precursor work, low metal background is often preferred; check CoA for ICP-MS screening when critical.
Stabilizers: None indicated for this item. If a stabilizer is used in related catalog items, it will be declared on the label/CoA. Absence of declaration generally implies neat material.
Batch-to-batch considerations: Phosphine oxide salts are typically robust; however, hygroscopic uptake can shift mass balance. We recommend standardizing on salt equivalency (mmol of cation) when stoichiometry is important.
Purchasing tip: Request CoA prior to large-scale use to verify salt form, counterion content, and any residual solvent from crystallization.
Reaction and Applications
Use domain: Organophosphorus heterocycle building block. The 1,4-azaphosphinan-4-one scaffold (phosphine oxide) serves as a precursor to ligands, functional materials, and P–N heterocycle libraries.
Ligand precursor chemistry: Reduction of the phosphine oxide to the corresponding P(III) phosphine enables access to P–N chelating ligands for transition-metal catalysis (e.g., hydrogenation, cross-coupling), with the saturated ring imparting conformational control.
Functionalization at nitrogen: Alkylation/acylation/sulfonylation after free-basing furnishes tertiary amides/sulfonamides or quaternary ammonium derivatives for ionic materials.
Alpha-functionalization at ring carbons: Deprotonation strategies (strong base) can enable substitution adjacent to the P-heteroatom, enabling diversity-oriented synthesis on the ring.
P-center transformations: Chlorination of P=O to P–Cl (via POCl3 derivatives or oxalyl chloride/Cl-silane systems) followed by substitution affords P–C, P–N, or P–O diversification while retaining the azaphosphinane framework.
Materials/probe development: The persistent P=O dipole can be leveraged for high dielectric materials, H-bonding probes, or as a polarity reporter in spectroscopy after appropriate tagging.
Practical notes:
Salt handling: Convert HCl salt to free base with a mild inorganic base (Na2CO3, K2CO3) in biphasic systems to avoid over-basic conditions that might induce ring opening.
31P NMR is a powerful handle for monitoring transformations; phosphine oxides typically appear downfield (positive ppm) vs. phosphines (upfield).
Drying: For reactions sensitive to trace water (e.g., chlorination or silyl-mediated reductions), dry thoroughly and operate under inert atmosphere.
Manufacturer Applications: Not provided in Product Data; the above expands on typical uses of azaphosphinane phosphine oxide salts in research synthesis.
Reaction Conditions
General conditions for common transformations of azaphosphinane-4-one HCl salts (literature-informed; adjust to your substrate and scale):
Free-basing the HCl salt:
Solvent: Water/MeOH or water/EtOAc biphasic.
Base: Na2CO3 or K2CO3 (2–3 equiv).
Temperature: 0–25 °C.
Workup: Separate organic layer containing free base; dry over Na2SO4; concentrate.
N-alkylation (to tertiary amine or quaternary ammonium):
Solvent: Acetonitrile, DMF, or acetone.
Base: DIPEA, K2CO3, or Cs2CO3 (1.5–2.0 equiv).
Electrophile: Alkyl halide or tosylate (1.1–1.5 equiv).
Temperature/time: 25–60 °C, 2–16 h.
Notes: Monitor by LC/MS and 31P NMR; minimize over-alkylation if tertiary amine is desired.
Reduction of P=O to P(III):
Reagent set A: HSiCl3 (3–4 equiv) with Et3N (3–4 equiv) in dry toluene or CH2Cl2, 0–25 °C to reflux, 2–24 h.
Reagent set B (greener): PMHS (4–6 equiv) with catalytic Ti(OiPr)4 (5–10 mol%) in toluene, 80–110 °C, 6–24 h.
Workup: Quench cautiously with MeOH/aq. NaHCO3; oxidize or protect P(III) as needed; handle under inert atmosphere.
Conversion to P–Cl intermediate:
Reagents: Oxalyl chloride (2–3 equiv) with catalytic DMF or Thionyl chloride, optionally in presence of a chlorosilane.
Solvent: CH2Cl2 or toluene (anhydrous).
Conditions: 0–25 °C to reflux; monitor 31P shift.
Expected yields: Highly substrate- and method-dependent; consult primary literature for closely related azaphosphinane systems.
Safety: Chlorosilanes and acid chlorides are corrosive and moisture-sensitive; use rigorous anhydrous technique and appropriate PPE.
Safety and Handling
Item-specific hazard data (Product Data):
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 guidance (consult SDS for authoritative instructions):
Potential hazards: Organophosphorus compounds can cause eye/skin irritation; hydrochloride salts are acidic and may be corrosive to eyes/mucosa in concentrated form. Phosphine oxides are not organophosphate esterase inhibitors; nevertheless, avoid inhalation and ingestion.
PPE: Safety glasses or goggles, lab coat, and chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid dust/aerosol exposure.
Handling: Minimize dust generation; avoid contact with strong bases (will liberate the free base) and strong oxidizers/reductants incompatible with ammonium salts. Prevent moisture uptake if hygroscopic by working quickly with capped containers.
Incompatibilities: Strong bases (deprotonation), strong dehydrating agents, and reagents that react with chloride under strongly acidic conditions. Avoid mixing with azides or cyanides in acid due to potential gas release (general acid-salt caution).
First aid (summary): If on skin/eyes, rinse cautiously with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth; do not induce vomiting; seek medical attention in all cases of significant exposure.
Fire: Use water spray, CO2, dry chemical, or foam. Combustion may produce phosphorus oxides and nitrogen oxides; wear self-contained breathing apparatus.
Always defer to the product-specific SDS for GHS codes, exposure limits, spill response, and disposal procedures.
Solvent Selection
Applicability: As a charged hydrochloride salt, solvent choice primarily affects solubility and reactivity of the amine site and handling of the phosphine oxide.
General solubility/miscibility profile (literature-informed, non-spec):
Water and polar protic (MeOH, EtOH): Typically high solubility due to ammonium chloride character.
Polar aprotic (DMSO, DMF, NMP, MeCN): Good solubility; useful for coupling or derivatization steps.
Ethers and esters (THF, EtOAc): Variable; often improved upon conversion to the free base.
Hydrocarbons (toluene, hexanes): Poor solubility as the HCl salt; free base form may be more compatible.
When to choose the HCl salt vs free base:
HCl salt: Preferred for storage, weighing accuracy, and minimizing amine volatility/odor. Suitable for aqueous-phase transformations (e.g., salt metathesis) and for reactions tolerant to acidic media.
Free base: Preferred for nucleophilic substitutions, base-mediated couplings, or when solubility in nonpolar organic media is required. Generate in situ by neutralization with a stoichiometric base (e.g., DIPEA, Na2CO3) in the reaction solvent.
Practical tips:
For moisture-sensitive steps downstream (e.g., chlorination of P=O), first convert to free base and rigorously dry (e.g., azeotrope with toluene; high vacuum over P2O5 or molecular sieves).
If performing aqueous workups, anticipate strong partitioning of the HCl salt into the aqueous phase; basify to extract the free base into organic solvent.
Storage and Reconstitution
Item-specific (Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for this class (non-spec):
Container: Store in a tightly closed, chemically compatible container with desiccant if hygroscopic. Protect from prolonged exposure to moisture to prevent caking or deliquescence of the HCl salt.
Inert atmosphere: Not strictly required for the phosphine oxide salt; optional nitrogen/argon blanket may help for long-term storage.
Light sensitivity: No particular photolability expected for saturated heterocycles; store away from direct sunlight as good practice.
Reconstitution/preparation of solutions:
Aqueous: Dissolve directly in deionized water or buffer; adjust pH only if needed for downstream applications.
Organic: For better solubility in less polar organic solvents, first convert to the free base. Alternatively, use polar aprotic solvents (DMSO, DMF, MeCN) for the HCl salt.
Filtration: If particulates are present, sterile-filter through 0.22 µm for assay use (research only).
Freeze–thaw: Solid form is preferred; if solution storage is necessary, aliquot to minimize freeze–thaw cycles. Verify stability by 31P NMR/LC before critical use.
Disposal: Follow institutional and local regulations for organophosphorus compounds; consult SDS for specifics.
Structure and Identity
Brief: 4-Methyl-1,4λ5-azaphosphinan-4-one hydrochloride is a saturated six‑membered P–N heterocycle bearing a pentavalent phosphorus(V)=O (phosphine oxide) at ring position 4, N in the ring, and a 4‑methyl substituent; isolated as the hydrochloride salt of the ring nitrogen.
Item-specific (Product Data):
CAS: 945459-80-3
CID: 66833053
InChIKey: 188630 (as provided; note: atypical format for an InChIKey)
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/literature-based description):
Core ring: 1,4-azaphosphinane (six-membered ring containing one nitrogen and one phosphorus).
Oxidation state: P(V) phosphine oxide (P=O) at the 4-position (λ5 notation indicates pentavalent phosphorus).
Substitution: Methyl group at C4; the hydrochloride indicates protonation at the ring nitrogen (forming an ammonium chloride salt) under isolation.
Stereochemistry: Ring can adopt chair conformations; the 4-methyl and P=O may be diaxial/diequatorial depending on conformation; no defined stereocenter unless substituted asymmetrically elsewhere.
2D structure in words: A chair-like six-membered ring with adjacent P and N atoms; at ring carbon-4 the phosphorus center (as part of the ring) bears a double-bonded oxide, and the same carbon bears a methyl substituent; the ring nitrogen is protonated and paired with chloride.
Synthetic Utility
Functional group handles and reactivity (literature-informed):
P=O center: Convertible to P(III) (phosphine) via reduction; can be chlorinated to P–Cl intermediates for further substitution. Strongly polar, aids crystallinity and purification.
Ring nitrogen: After free-basing, enables N-alkylation, acylation, sulfonylation, or quaternization to generate ionic derivatives.
Ring framework: The saturated six-membered P–N ring imparts conformational rigidity; substituents at C4 (methyl) influence steric and electronic environment around P for ligand design.
Named/typical transformations:
Reduction of phosphine oxides: Trichlorosilane/Et3N, polymethylhydrosiloxane (PMHS) with catalytic Ti, or dihydrosilanes under Lewis acid catalysis to access P(III) ligands.
P–Cl formation: Activation with oxalyl chloride in presence of chlorosilanes or via SOCl2/POCl3-based protocols to yield electrophilic P centers.
Cross-coupling adjuncts: The P(III) derivatives can be converted to phosphine ligands configured for Pd, Ni, or Rh catalysis.
N-derivatization: Mitsunobu-type or SN2 alkylations (for secondary amines) once the salt is neutralized; amide/sulfonamide formation using standard coupling reagents (EDC/HATU).
Retrosynthetic value:
The scaffold allows late-stage diversification at N and at P, decoupling steric tuning (via ring substitution) from electronic tuning (via P-oxidation state), enabling parallel synthesis of ligand or material libraries.
Target Specificity
Not applicable. This product is a small-molecule heterocycle, not a biological macromolecule (e.g., antibody, enzyme, or inhibitor) with defined target specificity. No antigen/epitope or species reactivity information is relevant.
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