Triisopropyl phosphate - ≥95% , CAS No.513-02-0

CAS: 513-02-0 Cat. No.: T332912 Formule: C₉H₂₁O₄P Poids moléculaire: 224.23 Numéro CE: 208-150-0 PubChem CID: 68188

GRADE & PURITY ≥95%

Synonyms

Phosphoric acid, tris(1-methylethyl) ester | Triisopropyl phosphate, analytical standard | MFCD00015490 | DTXSID90199295 | phosphoric acid triisopropyl ester | Phosphoric acid, triisopropyl ester | NCIOpen2_002645 | FT-0727890 | SCHEMBL80155 | tripropan-2

Storage

Room temperature

Shipped In

Normal

Specifications

Synonymes

Phosphoric acid, tris(1-methylethyl) ester | Triisopropyl phosphate, analytical standard | MFCD00015490 | DTXSID90199295 | phosphoric acid triisopropyl ester | Phosphoric acid, triisopropyl ester | NCIOpen2_002645 | FT-0727890 | SCHEMBL80155 | tripropan-2

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥95%

Noms et identifiants

Pubchem Sid

488184101

Sourires canoniques

CC(C)OP(=O)(OC(C)C)OC(C)C

IUPAC Name

tripropan-2-yl phosphate

InChIKey

OXFUXNFMHFCELM-UHFFFAOYSA-N

INCHI

1S/C9H21O4P/c1-7(2)11-14(10,12-8(3)4)13-9(5)6/h7-9H,1-6H3

Isomères SMILES

CC(C)OP(=O)(OC(C)C)OC(C)C

WGK Allemagne

3

PubChem CID

68188

Numéro ONU

1993

Groupe d'emballage

II

Poids moléculaire

224.23

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic phosphoric acids and derivatives
      • Subclass Phosphate esters
        • Level5 Alkyl phosphates
          • Level6 Trialkyl phosphates

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic phosphoric acids and derivatives
• Subclass: Phosphate esters
• Intermediate Tree Nodes: Alkyl phosphates
• Direct Parent: Trialkyl phosphates
• Alternative Parents: Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkyl phosphate - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Indice de réfraction: n20D1.4070 (lit.)
• Point d'éclair (°F): 73.4 °F
• Point d'éclair (°C): 23 °C
• Point d'ébullition (°C): 224° C (lit.)
• Poids moléculaire: 224.230 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 224.118 Da
• Monoisotopic Mass: 224.118 Da
• Topological Polar Surface Area: 44.800 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 168.000
• 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

Application Protocols

No assay or bioanalytical application protocols are specified for this item. As a general laboratory solvent/extractant, usage conditions are method-specific.

• For use as a co-solvent: Dry, add to reaction under inert atmosphere if required, and monitor by standard analytical techniques (GC, NMR, HPLC) to ensure compatibility.
• For liquid–liquid extraction: Establish distribution coefficients and phase disengagement times at small scale before scale-up; consider viscosity and temperature effects.

Refer to your method SOPs and consult the primary literature for system-specific protocols.

Biological Roles

This product is a synthetic organophosphate triester intended for research and laboratory use. It does not have a defined biological role in metabolism.

• General context (literature/general):
  • Trialkyl phosphate esters are not endogenous biomolecules. Their interactions with biological systems are typically non-specific (hydrophobic partitioning, weak H-bond acceptance) rather than receptor-targeted.
  • Hydrolysis (enzymatic or chemical) could, in principle, yield isopropyl alcohol and phosphate under harsh or catalytic conditions, but triesters like TIP are comparatively resistant in neutral aqueous media.

No medical, diagnostic, or therapeutic use is intended or implied. For toxicological and environmental fate information, consult the SDS and current literature.

Buffer Applications

Triisopropyl phosphate is not a buffering agent and is not typically used to prepare aqueous buffer systems.

• If present in aqueous/biochemical workflows, it would at most be as a minor organic co-solvent or extractant phase, not as a pH buffer.
• For buffer preparation, consider established systems (e.g., phosphate, Tris, HEPES) rather than organophosphate triesters.

Green Alternatives

Context: As a high-boiling polar aprotic medium/extractant, TIP competes with other phosphate esters and polar solvents. Selection should balance performance, safety, and environmental profile.

Comparison (literature/general; qualitative):

• Triisopropyl phosphate (TIP):

  • Pros: Neutral, non-halogenated; thermal stability; lower viscosity than TBP; moderate coordinating ability; typically low odor and low vapor pressure relative to low-MW solvents.
  • Cons: Combustible organic; limited biodegradability data; not bio-based; potential aquatic toxicity must be assessed case-by-case.

• Tri-n-butyl phosphate (TBP):

  • Pros: Stronger extractant for metal separations; very low volatility; extensive process know-how.
  • Cons: Higher viscosity; persistence concerns; challenging to remove from waste streams.

• Green(er) alternatives depending on task:

  • For polar aprotic solvent roles: Cyclic carbonates (e.g., propylene carbonate) or bio-derived ethers (e.g., 2-MeTHF) may offer improved sustainability, but differ in coordinating ability and boiling point.
  • For extraction roles: Bio-based esters (e.g., triacetin) or ionic liquids/deep eutectic solvents can reduce VOC emissions; performance must be validated.

Guidance:

• Evaluate EHS metrics (boiling point, flash point, biodegradability) and process compatibility. Conduct solvent selection using life-cycle and safety criteria (e.g., CHEM21/PSC). Substitute only where performance and downstream separation remain acceptable.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is specified for this item; refer to CoA/Spec Sheet.

General context (literature/general):

• Some trialkyl phosphates are used industrially as plasticizers in coatings or packaging; however, triisopropyl phosphate is not a common pharmaceutical excipient.
• In a research/manufacturing setting, such esters might appear as processing aids or specialty solvents in non-aqueous steps, with rigorous removal prior to final drug substance/product.

No therapeutic or clinical use is implied. Compliance with relevant pharmacopeias (USP/EP/JP) is not established for this SKU unless explicitly stated in the CoA.

Physical Properties

Item-specific physical property specifications (for this SKU) are not provided in the Product Data.

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

• Literature/typical properties for triisopropyl phosphate (reference only; not product specifications):

  • Physical state/appearance: Colorless to pale liquid (literature/general)
  • Molecular weight: ~224.24 g/mol (computed from C9H21O4P, literature)
  • Qualitative polarity: Polar aprotic; good H-bond acceptor (phosphoryl O), poor donor (literature/general)
  • Volatility: Lower than small dialkyl phosphates; typically high-boiling, low vapor pressure (literature/general)
  • Solubility: Expected miscibility with many non-protic organic solvents; limited solubility in water (literature/general)

Notes:

• Exact BP, MP, density, refractive index, water content, UV cutoff, and impurity limits are Not specified for this item; refer to CoA/Spec Sheet.
• For rigorous process design, measure or verify properties under your conditions, and consult the SDS/CoA for current specifications.

Quality and Grades

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

Interpretive guidance (general):

• Trialkyl phosphate esters sold for laboratory use may be offered as technical, reagent, or high-purity grades. Higher grades typically control acidity (as phosphoric acid), residual alcohols, water content, and UV absorbance.
• For chromatographic or moisture-sensitive applications (e.g., organometallic catalysis), request specifications for water (Karl Fischer), acidity (mg KOH/g or ppm H3PO4), and residual alcohol content. If HPLC/UV grade is relevant, low background absorbance will be specified.
• Stabilizers: None are typically required for neutral phosphate esters. If any stabilizer is present, it should be listed on the CoA; none are specified for this item.
• Batch documentation: For scale-up or regulated work, obtain CoA with impurity profile, elemental analysis (if needed), and trace metal content. Values are Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• Laboratory roles (literature/general):
  • High-boiling polar aprotic solvent/co-solvent for reactions benefiting from a neutral, weakly coordinating environment.
  • Neutral phosphoryl donor ligand in liquid–liquid extraction of certain metal ions (though TBP is more common). TIP’s steric bulk can modulate extraction selectivity and kinetics.
  • In polymer and materials labs, trialkyl phosphates serve as plasticizers or flame-retardant co-additives; TIP may be explored where steric hindrance and lower viscosity versus TBP are preferred.
• Reactivity considerations:
  • Generally inert toward many nucleophiles at ambient temperature; hydrolysis/transesterification may occur under strong acid/base or with catalysts at elevated temperatures.
  • Not a common phosphorylating reagent compared to POCl3 or phosphoramidites; however, it can participate in exchange reactions under forcing conditions.
• Practical tips:
  • Drying: Treat with activated 3 Å molecular sieves or distill under reduced pressure if a dry solvent is required. Avoid prolonged heating with strong bases.
  • Degassing: For sensitive catalysis, sparge with inert gas or apply freeze–pump–thaw cycles to remove dissolved gases.
  • Materials compatibility: Phosphate esters can plasticize certain elastomers; verify compatibility with seals and tubing (e.g., nitrile vs. PTFE).
• Related methodologies (reference):
  • Extraction science: Similar principles to TBP-based extraction systems (e.g., solvating extractants for metal nitrato/chloro complexes), but system-specific benchmarking is advised.

Reaction Conditions

Item-specific recommended reaction conditions are not provided. The following are general, literature-based considerations when using triisopropyl phosphate (TIP) as solvent/co-solvent or extractant:

• Solvent use (general):
  • Atmosphere: Inert gas (N2/Ar) for moisture- or air-sensitive reactions.
  • Drying: Pre-dry with 3 Å molecular sieves; verify water content if critical.
  • Temperature: Suitable for elevated temperatures where lower-boiling ethers/esters would reflux; exact boiling point Not specified for this item; refer to CoA/Spec Sheet.
• Compatibility:
  • Acids/bases: Stable under neutral conditions; strong acids/bases catalyze transesterification/hydrolysis at elevated temperatures.
  • Metals/catalysts: Weakly coordinating; can modulate activity/selectivity in Lewis acid catalysis. Test catalyst tolerance, as phosphate esters can inhibit some catalysts.
• Extraction use (general):
  • Phase ratio and salting agents (e.g., nitrate, chloride) govern complexation and distribution for metal ions; TIP is generally less potent than TBP—optimize ligand concentration and aqueous acidity accordingly.
• Workup:
  • TIP’s high boiling point and low vapor pressure relative to common solvents require vacuum stripping or solvent exchange for removal.

Always pilot small-scale trials to establish rates, selectivity, and separation feasibility under your specific conditions.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
• General hazards (literature/general): Trialkyl phosphate esters are typically combustible liquids; they can cause eye/skin irritation and may be harmful if ingested or upon prolonged exposure. Avoid inhalation of mists.
• PPE: Wear appropriate gloves (e.g., nitrile), lab coat, and eye protection (chemical splash goggles). Use in a chemical fume hood to avoid aerosol/mist exposure.
• Incompatibilities (general): Strong acids/bases (can catalyze transesterification or hydrolysis), strong oxidizers. Avoid moisture contamination in applications requiring low acid/alcohol content.
• Reactivity notes: Stable under ambient conditions; hydrolysis is typically slow at neutral pH but can be accelerated by heat and catalysts. Not known to form peroxides.
• First aid overview (general guidance; defer to SDS):
  • 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; seek medical advice. Do not induce vomiting unless directed by medical personnel.
• Fire-fighting: Use dry chemical, CO2, or alcohol-resistant foam. Combustion may produce phosphorus oxides; firefighters should wear self-contained breathing apparatus.
• Spill response: Absorb with inert material (vermiculite, diatomaceous earth), collect for disposal. Prevent entry into drains.

Always consult the product-specific SDS for authoritative safety information.

Solvent Selection

Triisopropyl phosphate (TIP) functions as a high-boiling, polar aprotic organic medium and weakly coordinating ligand/solvent in certain extractions.

• Polarity and coordination (literature/general):
  • Polar aprotic with a strongly polarized P=O bond; effective H-bond acceptor, negligible donor capacity.
  • Coordinates weakly to hard Lewis acids (e.g., metal cations) via the phosphoryl oxygen; far less coordinating than phosphine oxides like TOPO but more than simple ethers.
• Miscibility profile (general):
  • Typically miscible with many organic solvents (aromatics, chlorinated, esters, ketones). Water solubility is limited.
• When to choose TIP (general guidance):
  • As a high-boiling diluent or co-solvent when a neutral, thermally stable phosphate environment is desired.
  • In liquid–liquid extraction systems requiring a neutral phosphoryl donor (by analogy to TBP), noting that TIP has lower viscosity and higher volatility than tri-n-butyl phosphate.
• Alternatives/comparisons (general):
  • TBP (tri-n-butyl phosphate): stronger extractant for many metal ions; higher bp and viscosity, lower volatility; widely used in metal separations.
  • Trialkyl phosphates with smaller alkyls (e.g., triethyl phosphate) are more volatile and lower viscosity but often more water soluble.

For analytical separations or moisture-sensitive catalysis, pre-dry TIP (e.g., 3 Å molecular sieves) and verify water content per your method requirements.

Storage and Reconstitution

• Storage (item-specific from Product Data): Room temperature.
• Shipping (item-specific): Shipped under normal conditions.
• Container: Store tightly closed in compatible containers (glass or compatible fluoropolymer-lined caps). Minimize headspace if moisture uptake is a concern.
• Handling/storage guidance (general):
  • Keep away from strong oxidizers, strong acids/bases, and ignition sources.
  • If ultra-dry solvent is needed, dry over activated 3 Å molecular sieves, then dispense under inert gas. Record water content if process-critical.
• Reconstitution: Not applicable; supplied neat as a liquid. If solidification occurs at low temperatures, gently warm to ambient and mix thoroughly before use.
• Stability: Generally stable under ambient conditions. Avoid prolonged exposure to moisture and elevated temperatures in the presence of acids/bases to limit hydrolysis or transesterification.

Always refer to the product’s CoA and SDS for definitive storage and handling instructions.

Research Use Only: For research use only; not for human or veterinary use.

Structure and Identity

Triisopropyl phosphate is a trialkyl phosphate ester featuring a central phosphoryl (P=O) group bearing three isopropoxy substituents.

• Item-specific registry data (from Product Data):

  • CAS: 513-02-0
  • InChIKey: 269922 (as provided; consult CoA/SDS for a full identifier)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature identity (for reference; not item specifications):

  • Synonyms: TIP; Phosphoric acid triisopropyl ester; Triisopropyl phosphate
  • Molecular formula: C9H21O4P (literature)
  • Molecular weight: ~224.24 g/mol (literature)
  • Representative SMILES: CC(C)OP(=O)(OC(C)C)OC(C)C (literature)

• Structural features (general chemistry description):

  • Functional groups: One phosphoryl P=O; three P–O–alkyl (isopropoxy) linkages; no stereocenters at phosphorus in the free ester; each isopropyl is prochiral but achiral overall.
  • 2D structure in words: A tetra-coordinated phosphorus center double-bonded to oxygen and single-bonded to three oxygen atoms, each connected to a secondary (isopropyl) carbon, yielding three –O–CH(CH3)2 arms around a central P=O.
  • Class: Neutral organophosphate triester; polar, weakly coordinating Lewis base at the phosphoryl oxygen.

Synthetic Utility

From a synthetic strategy perspective, triisopropyl phosphate (TIP) serves primarily as an inert, polar aprotic medium and weakly coordinating phosphoryl donor rather than as a direct reagent.

• Functional elements:
  • P=O moiety: strong dipole; can stabilize cationic transition states and coordinate to Lewis-acidic metals, subtly influencing selectivity and rates in catalysis or extraction.
  • Three isopropoxy groups: confer steric hindrance and reduce susceptibility to nucleophilic displacement under mild conditions.
• Utility highlights (literature/general):
  • As co-solvent in high-temperature condensations or polymerizations requiring neutral conditions where ethers may be too volatile.
  • As a diluent or modifier in metal-ion extraction systems where tuning donor strength and viscosity is essential.
  • Potential role as a leaving-group reservoir in transesterification under strong acid/base catalysis, though less reactive than smaller trialkyl phosphates.
• Retrosynthetic note:
  • TIP itself is commonly prepared by alcoholysis of phosphorus oxychloride or via phosphorylation routes using isopropanol, underscoring its stability under neutral conditions.

When selecting TIP for synthesis, benchmark against phosphine oxides (stronger donors) and carbonates/esters (greener or more volatile) based on the required donor strength, bp, and downstream separations.

Target Specificity

Not applicable. This product is a small-molecule organophosphate solvent/extractant, not a biological targeting reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.