This compound belongs to the class of organic compounds known as organophosphorus compounds. These are organic compounds containing the phosphorus atom.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Point de fusion (°C)
69-72° C
Poids moléculaire
178.210 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
0
Rotatable Bond Count
0
Exact Mass
178.091 Da
Monoisotopic Mass
178.091 Da
Topological Polar Surface Area
0.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
216.000
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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Application Protocols
Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic protocols, refer to literature on phosphaalkyne cycloadditions and organometallic reactions, and optimize conditions as outlined under Reaction Conditions.
Biological Roles
This product is a specialized organophosphorus synthetic reagent and is not designed for biological systems.
Known biological roles: None established for 1-adamantylphosphaethyne (no natural occurrence expected). Any interaction with biomolecules would be non-specific and driven by the high reactivity of the polarized C≡P unit rather than a defined biochemical function (literature/general).
Biocompatibility: Not assessed; likely incompatible with aqueous/protic environments due to hydrolytic and addition reactions at the C≡P bond.
Research context: If used in chemical biology (e.g., as a reactive handle in abiotic conjugation chemistry), operations must be conducted in strictly anhydrous, aprotic media with immediate quench strategies; such uses are exploratory and outside typical bioassay conditions.
Item-specific biological data (toxicity, metabolism, uptake): Not specified for this item; refer to SDS and CoA.
Buffer Applications
Not typically applicable. 1-Adamantylphosphaethyne is moisture-sensitive and reactive toward protic media; it is unsuitable for aqueous buffer systems. For laboratory use, focus on strictly anhydrous, aprotic organic solvents as outlined under Solvent Selection and Reaction & Applications.
Green Alternatives
Green chemistry considerations focus on solvent choice, containment, and minimizing energy input, given that the C≡P motif is inherently reactive.
Preferred greener solvents (when compatible)
2-Methyltetrahydrofuran (2-MeTHF): biorenewable ether with lower peroxide formation tendency than THF; good balance of polarity and stability for many cycloadditions.
Cyclopentyl methyl ether (CPME): hydrophobic, low water miscibility, high stability; can reduce side reactions and facilitate workups.
Heptane or cyclohexane instead of toluene/hexane blends to reduce aromatics exposure.
Comparison (general)
THF vs 2-MeTHF: similar solvating power; 2-MeTHF often enables lower temperatures and easier phase separations, but must still be rigorously dried.
Toluene vs CPME: CPME offers higher hydrophobicity and often better stability toward acids/bases; toluene may provide higher solubility for some partners.
Process-intensity reductions
Run at the lowest temperature that affords selectivity to avoid excessive cooling/heating cycles.
Continuous-flow addition of the phosphaalkyne can improve safety and reduce solvent volumes.
Waste minimization
Use scavengers/resins for Lewis acids to streamline quench/neutralization.
Favor catalytic over stoichiometric activators.
Trade-offs: Greener ethers can still participate in undesired pathways with highly reactive partners; always conduct compatibility tests at micro-scale before substitution. Item-specific green data: Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
No direct excipient or formulation role is expected for 1-adamantylphosphaethyne.
Pharmacopeial status: Not listed (general comment).
Manufacturing context: Any use would be limited to early-stage discovery chemistry as a building block/intermediate generator for phosphorus-containing scaffolds under strictly anhydrous conditions.
Residual solvent/impurity expectations and cGMP controls: Not applicable to this research-use-only material. If derivatives enter later-stage programs, separate sourcing/specifications would be required.
Item-specific pharmaceutical/excipient information: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific specifications (for this catalog entry):
Appearance: 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.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed properties for 1-adamantyl-substituted phosphaalkynes (guidance only — verify experimentally):
Phase/volatility: low–moderate volatility; typically handled neat or as cold, inert solutions due to reactivity of the C≡P unit.
Density, refractive index, UV cutoff: data scarce in open literature for this specific derivative.
Thermal behavior: phosphaalkynes can oligomerize or undergo cycloadditions upon warming or in the presence of catalysts/acids/bases; refrigeration helps preserve monomer.
Solubility profile: expected high solubility in nonpolar and moderately polar aprotic organic solvents (pentane, hexane, toluene, Et2O, THF) and negligible solubility in water (literature/class behavior).
Acid/base: the C≡P unit is weakly basic at phosphorus and electrophilic at carbon; no relevant pKa in water (literature/class behavior).
General notes for practitioners:
Avoid protic media; moisture can induce decomposition or downstream reactivity.
Work cold (−78 to 0 °C) and under inert atmosphere to limit oligomerization.
Because reliable numeric constants (bp/mp/logP) are not broadly reported for this exact compound, determine working values empirically on small scale where needed.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet. The Certificate of Analysis will provide batch-level assay, residual solvent profile, and other analytical data (e.g., NMR, GC, elemental analysis) as applicable.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Some phosphaalkyne derivatives are shipped cold and under inert atmosphere without added stabilizers to preserve reactivity.
What “research use only” means here:
Intended for laboratory chemical synthesis and mechanistic studies; not for human or veterinary use, diagnostics, or food/cosmetic applications.
Recommended quality verification on receipt (good practice):
31P NMR: sharp resonance characteristic of phosphaalkyne P; absence of broad oligomer signals indicates good quality.
13C NMR: sp-carbon of C≡P typically far downfield; confirms integrity of the triple bond.
IR: strong band in the region associated with C≡P stretch (literature: typically ~1200–1300 cm−1; verify).
Handling implications:
Maintain the cold chain; minimize headspace oxygen/moisture.
If supplied as a solution, note the solvent grade (anhydrous) and expiry guidance on the CoA.
UV/metal/peroxide specifications: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
1-Adamantylphosphaethyne is a sterically shielded phosphaalkyne (R–C≡P) useful as a reactive C≡P synthon. The adamantyl group enhances kinetic stability while preserving the characteristic reactivity of the C≡P moiety.
Representative application areas (literature/general):
Cycloadditions
[2+2], [2+3], and [4+2] cycloadditions with alkenes, alkynes, nitriles, and 1,3-dipoles to access P-containing heterocycles (e.g., phospholes, phosphinidenes adducts, and phosphaaza-heterocycles).
Thermal vs. Lewis acid/transition-metal catalyzed variants allow tuning of regioselectivity at the polarized C≡P bond.
Formation of phosphaalkenes and phosphacumulenes
Nucleophile-induced addition to the C of C≡P followed by rearrangement/elimination can furnish P=C species valuable in main-group chemistry.
Coordination/organometallic chemistry
Acts as a ligand or insertion partner to low-valent metal centers; reactivity parallels/is complements to alkynes but with distinct P-based donor properties.
Polymer/oligomer formation studies
Controlled oligomerization of phosphaalkynes generates conjugated P-containing materials; the adamantyl substituent can modulate aggregation and solubility.
Practical tips:
Use sub-ambient temperatures (−78 to 0 °C) to dose and mix, warming judiciously to initiate cycloaddition.
Choose non-protic, dry solvents; toluene and ethers are common.
Monitor by 31P NMR to follow consumption of C≡P and appearance of product resonances.
Catalyst screens: Lewis acids (e.g., AlCl3, BF3·OEt2) and late-transition metals (e.g., Ni, Pd, Pt) can profoundly alter pathways; run small test reactions first.
Reaction Conditions
General literature-guided conditions for phosphaalkyne transformations (optimize per substrate):
Atmosphere and setup
Strictly inert (Ar/N2); flame-dried glassware; anhydrous, degassed solvents. Syringe or cannula transfer recommended.
Temperature
Dosing/mixing: −78 to 0 °C to minimize premature side reactions.
Reaction: −78 to ambient (occasionally to 60 °C) depending on partner and catalyst; monitor carefully as exotherms can occur.
Concentration/time
0.02–0.2 M typical for cycloadditions; slow addition of the phosphaalkyne over 10–120 min can improve selectivity. Total reaction times range from minutes to several hours.
Catalysis/activation (examples)
Lewis acids (e.g., BF3·OEt2, AlCl3): accelerate [2+2]/[4+2] pathways; start with catalytic loadings (2–10 mol%).
Transition metals (e.g., Ni(0), Pd(0/II), Pt(II)): enable coordination/insertion and annulation chemistry; 1–10 mol% typical. Add phosphine scavengers post-reaction if needed.
Thermal, catalyst-free variants are feasible with highly activated partners (nitrile oxides, azides, electron-poor alkenes/alkynes).
Monitoring and workup
Track by 31P NMR (disappearance of C≡P signal; emergence of P-containing product signals) and TLC/GC if volatile partners used.
Quench Lewis acids with solid bases or resin scavengers; avoid aqueous quench until C≡P is fully consumed or masked.
Yields/selectivity
Reported outcomes vary widely (30–90% typical in literature depending on partner/catalyst). Run micro-scale screens to define optimal conditions before scale.
Note: Numeric conditions are general literature guidance for phosphaalkynes; item-specific validated conditions are not provided for this SKU.
Safety and Handling
Item-specific hazard information provided: none. Always consult the SDS for authoritative guidance.
General safety considerations for phosphaalkynes and related organophosphorus reagents (literature/class-based):
GHS/CLP: Not specified for this item; refer to SDS. Expect potential flammability and acute toxicity/irritancy typical of low-molecular-weight organophosphorus compounds.
Special risks: the polarized C≡P moiety is highly reactive and may undergo exothermic polymerization/cycloadditions, particularly in the presence of acids, bases, Lewis acids, or transition-metal catalysts.
Incompatibilities: strong acids/bases, oxidizers, moisture, protic solvents, and radical initiators. Avoid contact with halogens and peroxides.
Atmosphere: handle strictly under inert gas (N2/Ar). Use air-free techniques (Schlenk or glovebox). Degas solvents thoroughly.
Temperature: keep cold. Store and manipulate on ice or in a cold bath when feasible to suppress side reactions.
PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., laminated or nitrile); use within a fume hood. For scale-up, add splash protection.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Skin/eye contact: immediate decontamination with copious water; remove contaminated clothing; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Waste: collect under inert solvent if needed; quench cautiously via controlled reactions recommended in the literature, or consign as hazardous organophosphorus waste per institutional/EHS policy.
Solvent Selection
Guidance for choosing solvents for 1-adamantylphosphaethyne (class-based best practices):
Polarity/miscibility
Nonpolar to moderately polar aprotic solvents are preferred: pentane, hexanes, cyclohexane, toluene, diethyl ether, MTBE, and dry THF.
Avoid protic solvents (water, alcohols) and strongly nucleophilic dipolar aprotics (e.g., DMSO, DMF) that can engage the C≡P unit or accelerate side reactions.
Dielectric and coordinating character
Hydrocarbons (ε ~2): maximize kinetic stability, minimize activation of cycloadditions; good for storage/transfer at low T.
Ethers (ε ~4–7): enhance solubility and facilitate reactions with polar reagents; use scrupulously dry and cold to reduce unintended reactivity.
Practical choices by task
Storage/stock solutions: dry pentane/hexane or toluene at −20 to 0 °C under Ar.
Cycloaddition chemistry: toluene, Et2O, or THF at −78 to 25 °C depending on partner reactivity; toluene often balances solubility and stability.
Metal-complex chemistry: aromatic hydrocarbons, Et2O/THF, or chlorinated solvents if compatible with the metal precursor (test stability first).
Comparison (literature-guided)
Hydrocarbons: highest stability, lower rates.
Ethers: greater reactivity/solubility, increased risk of side reactions.
Chlorinated solvents: powerful solvents but may promote decomposition with some organophosphorus reagents; use only after preliminary tests.
Always degas and dry solvents rigorously (molecular sieves, solvent stills, or solvent purification systems).
Storage and Reconstitution
Item-specific storage and shipping
Storage: Store at −20 °C (as provided in Product Data).
Shipping: Shipped in ice chest with ice pads to maintain a cold chain.
General handling guidance for this class of reagents
Atmosphere: keep under inert gas (Ar/N2). Use air-free techniques; protect from moisture and light (amber vials recommended).
If supplied neat: pre-cool receiving vial; transfer by syringe/cannula at low temperature.
If supplied in solution: maintain the anhydrous solvent system; do not evaporate to dryness unless necessary and conditions are strictly inert and cold.
Thawing/aliquoting: allow to equilibrate to handling temperature under inert gas; rapidly aliquot into pre-chilled, inerted vials to minimize exposure time. Re-freeze promptly.
Shelf life, stabilizers, and exact solvent (if any): Not specified for this item; refer to CoA/Spec Sheet.
Before use: verify integrity by 31P NMR/IR for the C≡P signature. If broad byproducts are evident, consider low-temperature filtration or re-purification under inert atmosphere.
Structure and Identity
Brief: 1-Adamantylphosphaethyne is a phosphaalkyne (R–C≡P) bearing a bulky, rigid 1-adamantyl substituent that stabilizes the highly polarized C≡P unit.
Item-specific identifiers
SKU: A332908
Product name: 1-Adamantylphosphaethyne
CAS: 101055-70-3
PubChem CID: 2784593
InChIKey (as provided): 275302
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description)
Functional groups: terminal phosphaalkyne (C≡P) conjugated to a tertiary carbon of the adamantyl cage.
Ring system: adamantane polycyclic cage (tricyclo[3.3.1.13,7]decane framework) as the substituent; no aromatic rings.
Stereochemistry: none expected at the ipso carbon; adamantyl framework contains no stereogenic centers in this substitution pattern.
Bonding: strong, short, polarized triple bond between carbon and phosphorus (C≡P), isoelectronic to alkynes (C≡C) but more reactive toward cycloadditions and coordination.
2D description in words
A quaternary bridgehead carbon of the adamantyl cage is sp-hybridized to the C of a C≡P unit, giving R–C≡P where R is 1-adamantyl. The cage confers steric protection around the C≡P axis while leaving the π-system accessible.
Formula/MW
Item-specific molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Item-specific molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (for the structure R = 1-adamantyl): approximate formula C11H15P; approximate formula mass ~178 g/mol (literature/computed; verify against CoA).
Synthetic Utility
Key reactive element: the C≡P (phosphaalkyne) bond combines alkyne-like π-systems with a lone pair on phosphorus, creating orthogonal reactivity not accessible with C≡C alkynes.
Electrophilic carbon, nucleophilic phosphorus
Nucleophiles can add to the sp-carbon, enabling conversion to phosphaalkenes (P=C) or phosphaallenes with subsequent steps.
The phosphorus can coordinate to metals or accept electrophiles, modulating downstream reactivity.
Cycloaddition platform
[2+2], [2+3] (dipolar), and [4+2] pathways give access to P-containing rings (phospholes, phosphinines, and related frameworks) with substituent control via the bulky adamantyl group.
Organometallic compatibility
Engages in π-complexation and insertion with low-valent metals; useful for assembling metal–P–C linkages, unique ligands, or metal-promoted functionalizations that diverge from standard alkyne chemistry.
Retrosynthetic value
Treat the reagent as a masked “C≡P” synthon enabling late-stage installation of phosphorus into π-frameworks.
Selectivity lever: adamantyl bulk
The rigid steric profile often biases approach vectors in cycloadditions, improving regio- or chemoselectivity and reducing uncontrolled oligomerization compared with less hindered phosphaalkynes.
Analytical control: 31P NMR is highly diagnostic throughout; combine with IR (C≡P stretch) and HRMS to confirm incorporation patterns in complex products.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, protein, or probe). No antigen/epitope/isotype or species reactivity data are relevant.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). 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 101055-70-3, the molecular formula is C11H15P, and the molecular weight is 178.21 g/mol. InChIKey PEMKIUPAYNEFGZ-UHFFFAOYSA-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.
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