Phosphoric acid, bis(2-methylphenyl) ester - ≥95% , CAS No.35787-74-7

CAS: 35787-74-7 Cat. No.: P1029628 Formule: C₁₄H₁₅O₄P Poids moléculaire: 278.24 PubChem CID: 92302

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CC1=CC=CC=C1OP(=O)(O)OC2=CC=CC=C2C
• IUPAC Name: bis(2-methylphenyl) hydrogen phosphate
• InChIKey: OHRCKPRYDGSBRN-UHFFFAOYSA-N
• INCHI: 1S/C14H15O4P/c1-11-7-3-5-9-13(11)17-19(15,16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H,15,16)
• Isomères SMILES: CC1=CC=CC=C1OP(=O)(O)OC2=CC=CC=C2C
• PubChem CID: 92302
• Poids moléculaire: 278.24

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic phosphoric acids and derivatives
• Subclass: Phosphate esters
• Intermediate Tree Nodes: Aryl phosphates
• Direct Parent: Aryl phosphodiesters
• Alternative Parents: Phenoxy compounds Toluenes Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aryl phosphodiester - Phenoxy compound - Toluene - Benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aryl phosphodiesters. These are aryl phosphates in which the phosphate is esterified at exactly two positions.
• 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

• Poids moléculaire: 278.240 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 278.071 Da
• Monoisotopic Mass: 278.071 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 305.000
• 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

Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic or analytical use, follow standard organophosphorus handling and reaction protocols as outlined under Reaction Conditions.

Biological Roles

This is a synthetic diaryl phosphate intended for laboratory research. It does not have a known endogenous biological role.

• General context (literature): Aryl phosphate esters are structural mimics used in mechanistic enzymology (e.g., probing phosphoryl transfer), but specific biological activity for bis(2-methylphenyl) phosphate has not been established.
• No medical, diagnostic, or therapeutic use is implied. For any biochemical assays, validate concentration, vehicle, and controls empirically.

Buffer Applications

Not typically used as a buffer component. As a hydrophobic diaryl hydrogen phosphate, it lacks the aqueous solubility and pKa spacing desirable for conventional laboratory buffers. If phosphate functionality is required in aqueous systems, use established inorganic or organic phosphate buffers (e.g., phosphate saline buffers, phosphoric acid/NaH2PO4/Na2HPO4) instead.

Green Alternatives

• Solvent choices:
  • Prefer ethyl acetate, 2-MeTHF, or cyclopentyl methyl ether (CPME) over chlorinated solvents when solubility permits; these reduce halogenated waste.
  • Use toluene or 2-MeTHF for high-temperature operations in place of xylene or chlorinated media.
• Catalysis over stoichiometry:
  • For acid-catalyzed transformations, consider catalytic organic acids (e.g., p-toluenesulfonic acid) or solid acids (Amberlyst-15) that are easier to separate and recycle, provided reaction scope allows.
• Dehydrative couplings:
  • Replace DCC with water-compatible carbodiimides (EDC) or green coupling strategies (e.g., CDI, propanephosphonic anhydride—T3P in EtOAc) to minimize hazardous urea waste; verify compatibility with phosphate chemistry.

Comparison snapshot (general guidance):

• DCM vs EtOAc/2-MeTHF:
  • Environmental: Halogenated waste vs biodegradable/renewable solvent options.
  • Performance: DCM offers excellent solubility/inertness; EtOAc/2-MeTHF may require larger volumes but simplify workup and reduce toxicity.
• Homogeneous vs solid acids:
  • Workup: neutralization and saline waste vs simple filtration and reuse.
  • Selectivity: homogeneous acids may offer higher rates; solid acids trade some rate for sustainability and ease of handling.

Note: Select greener options case-by-case; confirm that alternative media do not promote undesired transesterification of the phosphate.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

• General note: Diaryl phosphate esters are not common pharmaceutical excipients due to hydrophobicity and limited regulatory precedence. Any use would be limited to non-clinical research and process development studies (e.g., as an acid catalyst or intermediate) and must not be incorporated into products for human or veterinary administration.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (literature): ~278.24 g/mol (C14H15O4P)
• Physical state at ambient conditions (literature/typical for diaryl hydrogen phosphates): viscous liquid or low-melting solid; exact MP/BP not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cut-off, water content, residual peroxides, metal content: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/typical behavior):
  • Water: low solubility due to hydrophobic aryl groups despite presence of acidic P–OH; can form salts to increase aqueous solubility.
  • Organic solvents: soluble in common aprotic organics (e.g., dichloromethane, toluene, ethyl acetate, acetone); miscibility depends on solvent polarity.
• Acidity (literature/typical): diaryl hydrogen phosphates are moderately strong Brønsted acids (pKa1 commonly ~1–2 in water for diphenyl analogs); exact pKa for the bis(2-methylphenyl) derivative not specified.
• Partitioning (literature/expected): hydrophobic; logP expected to be positive; exact value not specified for this item.

Note: For authoritative, lot-specific physical constants and any chromatographic suitability parameters, consult the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grades (general guidance):
  • Analytical/Reagent grade: tight control of inorganic impurities and assay; suitable for most synthetic and analytical tasks.
  • HPLC grade (for solvents): low UV absorbance and particulate; not typically applicable to this solid/liquid reagent class but relevant if used as mobile phase additive.
  • Trace metal or electronic grade: minimized metal content for catalysis-sensitive workflows.
• Stabilizers/inhibitors: Not specified for this item. Diaryl hydrogen phosphates typically do not require polymerization inhibitors, but moisture control can be important to suppress hydrolysis; always confirm on the CoA.
• What to check on receipt (best practices):
  • Appearance match to CoA, assay or NMR purity, acidity (acid number or titration), residual phenol content, water by Karl Fischer if hydrolysis is a concern.
  • For sensitive transformations (e.g., catalysis), verify metals by ICP if a low-metal spec is required.
• Documentation: For method validation or regulated environments, request and retain the batch CoA, SDS, and any available impurity profiles or NMR spectra.

Reaction and Applications

• Phosphorylation building block (literature): Diaryl hydrogen phosphates can be converted to mixed or triester phosphates, enabling installation of phosphate protecting groups on alcohols or phenols under dehydrative coupling conditions (e.g., carbodiimide-mediated couplings with catalytic DMAP). Reaction efficiency benefits from water removal and base scavenging.
• Brønsted acid catalysis (literature): As a moderately strong, non-volatile organic-soluble acid, diaryl hydrogen phosphates can catalyze acetalizations, esterifications, and dehydration reactions in nonaqueous media. The ortho-methyl groups increase lipophilicity and can modulate acidity/solubility compared with the diphenyl analogue.
• Leaving group chemistry (literature): Aryl phosphate esters serve as good leaving groups in SN1/SN2’ manifolds under appropriate activation, enabling substitution on activated systems or participation in Mitsunobu-like manifolds where phosphate serves as an intermediate or protecting group.
• Salt formation: Neutralization with organic bases (e.g., tertiary amines) affords lipophilic phosphate salts useful as phase-transferable reagents or ionic co-catalysts.
• Materials/organophosphorus research: Diaryl phosphates are model compounds for studying hydrolysis kinetics, P–O bond cleavage mechanisms, and as precursors to tailored phosphate esters; the o-tolyl substituents impart steric bulk valuable in comparative studies.

Practical tips (general):

• Dry solvents and exclude water to limit competitive hydrolysis; use molecular sieves or Dean–Stark where appropriate.
• For esterification to triesters, use coupling agents (e.g., DCC/EDC) with catalytic nucleophilic acyl transfer catalysts (DMAP/PPy); monitor for phenol release.
• For selective monoactivation, pre-form amine salts to tune acidity and solubility; titrate back to free acid during workup.

Reaction Conditions

General, literature-based guidance for diaryl hydrogen phosphates; optimize for your substrate.

• Phosphorylation of alcohols (to triesters):
  • Typical setup: alcohol (1.0 equiv), diaryl hydrogen phosphate (1.1–1.5 equiv), DCC or EDC (1.2–1.8 equiv), catalytic DMAP (5–10 mol%).
  • Solvent: DCM, THF, or acetonitrile (anhydrous). Temperature: 0–25 °C initially, then allow to warm or stir overnight. Remove urea by filtration; purify by silica gel using nonbasic eluents.
• Acid-catalyzed transformations:
  • Use 1–10 mol% of the diaryl phosphate as a Brønsted acid catalyst for acetalization of carbonyls with diols, or for Fischer esterifications, in toluene or 2-MeTHF with Dean–Stark water removal. Temperatures: reflux; times: 2–12 h.
• Hydrolysis studies/control:
  • Aqueous buffers (pH 2–10) at 20–60 °C can be used to profile hydrolytic stability; expect acceleration under basic conditions with formation of o-cresol and inorganic/monoaryl phosphate (literature behavior). Avoid strong base during processing unless hydrolysis is intended.
• Monitoring:
  • 31P NMR for phosphorus speciation; 1H/13C NMR for aryl signals and o-cresol byproduct; LC–MS for mass balance.

Notes:

• The above are literature-style conditions; exact conditions for “Phosphoric acid, bis(2-methylphenyl) ester” may vary. Always run small-scale trials to establish kinetics and selectivity. No item-specific performance guarantees are implied.

Safety and Handling

• GHS classification, signal word, hazard (H) statements, and pictograms: Not specified for this item; refer to the SDS for definitive safety information.
• General hazards (literature/typical for aryl phosphate acids):
  • Corrosive/irritant potential to skin, eyes, and mucosa due to acidity.
  • May be harmful if swallowed or inhaled; avoid aerosol/mist generation.
• PPE and engineering controls:
  • Wear lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles.
  • Handle in a chemical fume hood; employ local exhaust during transfers.
• Handling guidance:
  • Avoid contact with bases, strong oxidizers, and reactive metals. Neutralization with bases generates corresponding phosphate salts; heat evolution possible.
  • Minimize exposure to moisture if purity is critical; hydrolysis to phenols and phosphates can occur slowly under aqueous/basic conditions.
  • Prevent contamination with alcohols if the free acid functionality must be preserved; esterification/transesterification may be acid-catalyzed under forcing conditions.
• First-aid overview (consult SDS for full instructions):
  • Skin/eye contact: Immediately flush with water for ≥15 min; remove contaminated clothing; seek medical attention.
  • Inhalation: Move to fresh air; obtain medical advice if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety (literature/typical):
  • Not highly volatile; combustion may produce CO/CO2 and phosphorus oxides; use standard extinguishing media (CO2, dry chemical, foam). Thermal decomposition can be irritating—firefighters should wear SCBA.
• Spill response: Absorb with inert material (vermiculite, diatomaceous earth), collect for disposal; avoid discharge to drains. Decontaminate surfaces with mild alkaline detergent if compatible.

Solvent Selection

This compound is a hydrophobic, moderately polarizable diaryl phosphate acid. Solvent choice should reflect its limited water solubility, acidity, and compatibility with downstream reactions.

• Polarity/miscibility (literature/typical):
  • Good solubility: dichloromethane (DCM), chloroform, toluene, ethyl acetate, acetone, acetonitrile.
  • Limited/variable: alcohols (may engage in acid–base or esterification chemistry under strong acid/heat).
  • Poor: water (unless neutralized to a salt), aliphatic hydrocarbons at room temp may require warming.
• When to choose which solvent:
  • DCM/CHCl3: extraction, chromatography, and reactions where mild Lewis basicity of the medium is acceptable.
  • Toluene: higher-temperature operations, azeotropic drying, and nonpolar media.
  • Ethyl acetate/MTBE: workups and crystallizations of salts or derivatives; greener than chlorinated options.
  • Acetonitrile/acetone: if modest polarity is needed and protic interactions must be minimized.
• Compatibility notes:
  • Avoid prolonged exposure in lower alcohols at elevated temperatures if free acid integrity is required (risk of transesterification/triester formation under strong acid catalysis).
  • For aqueous processing, consider forming a buffered salt (e.g., triethylammonium) to improve water miscibility, then back-convert if needed.
• Small comparison (general):
  • DCM vs EtOAc: DCM offers higher solubility and inertness; EtOAc is greener and supports easier waste handling.
  • Toluene vs MeCN: toluene favors nonpolar conditions/thermal stability; MeCN provides higher polarity for ionic partners.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from bases and oxidizers. Protect from prolonged moisture exposure to limit hydrolysis.
• Container: Use amber glass with PTFE-lined cap to minimize interaction and moisture ingress. If dispensing frequently, consider a desiccator or inert-atmosphere cabinet.
• Stability: Diaryl hydrogen phosphates are generally stable at ambient conditions when kept dry. Hydrolysis can occur over time in the presence of moisture, especially under basic conditions.
• Reconstitution/Preparation:
  • Not supplied lyophilized; no reconstitution required. For solution preparation, dissolve in a compatible anhydrous organic solvent (e.g., DCM, toluene, acetonitrile, ethyl acetate) at the desired concentration. Prepare fresh solutions for sensitive transformations.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Research use note: For research use only. Not for human or veterinary use.

Always consult the SDS for detailed storage incompatibilities and spill/fire response procedures.

Structure and Identity

Phosphoric acid, bis(2-methylphenyl) ester is a diaryl hydrogen phosphate featuring two o-tolyl (2-methylphenyl) groups bound to phosphorus via P–O–Ar linkages and one ionizable P–OH.

• Item-specific identifiers (from Product Data):

  • CAS: 35787-74-7
  • SKU: P1029628
  • Category: Life Science (research use only)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity details (general reference, not item-specific specifications):

  • Common name: di(o-tolyl) phosphate (hydrogen)
  • Molecular formula (literature): C14H15O4P (diaryl hydrogen phosphate with two o-tolyl groups)
  • Molecular weight (literature): ~278.24 g/mol
  • Core functional groups: tetrahedral phosphate P(V) center bearing one phosphoryl (P=O), two aryl phosphate esters (P–O–Ar), and one acidic hydroxyl (P–OH)
  • Structural description: a central phosphate with trigonal-pyramidal/tetrahedral geometry; two ortho-methyl-substituted phenyl rings attached through oxygen; the ortho-methyl groups introduce steric bulk proximal to the P–O bonds; one free acidic OH capable of forming salts/esters.

• Stereochemistry: none (achiral at phosphorus for the hydrogen diester).

Synthetic Utility

• Functional group profile:
  • Brønsted-acidic P–OH enables salt formation and catalysis in nonaqueous media.
  • Two aryl phosphate esters (P–OAr) make the phosphorus center an electrophile under dehydrative conditions, allowing conversion to mixed/triester phosphates.
• Transformations (literature):
  • Phosphorylation of alcohols/phenols via carbodiimide coupling (DCC/EDC) with nucleophilic catalysts (DMAP), forming triaryl/aryl–alkyl phosphates and releasing o-cresol.
  • Protection strategies where phosphate acts as a temporary masking group for diols/polyols; removal via hydrolysis or nucleophilic displacement.
  • Generation of lipophilic phosphate salts with tertiary amines to tune solubility and phase-transfer behavior.
• Retrosynthetic value:
  • Serves as a convergent handle to introduce phosphate under mild conditions compared with harsher reagents like POCl3; steric and electronic effects of o-tolyl groups can modulate reactivity relative to diphenyl phosphate.
• Practical notes:
  • Exclude moisture, particularly when targeting high yields of triesters.
  • Monitor by 31P NMR; diaryl hydrogen phosphates typically resonate around −10 to −5 ppm (external H3PO4 = 0 ppm), shifting downfield upon esterification (literature, compound-dependent).

Target Specificity

Not applicable. This product is a small-molecule organophosphorus reagent and is not an antibody, enzyme, or biological targeting agent. No target, epitope, clone, or species reactivity data are provided.