2-(Dimethylphosphoryl)benzoic acid - ≥98% , CAS No.79317-57-0

CAS: 79317-57-0 Cat. No.: D1289676 EG-Nummer: 845-633-0 PubChem CID: 563163

GRADE & PURITY ≥98%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

CP(=O)(C)C1=CC=CC=C1C(=O)O

IUPAC Name

2-dimethylphosphorylbenzoic acid

InChIKey

ZVUKMPRMHHHNQW-UHFFFAOYSA-N

INCHI

1S/C9H11O3P/c1-13(2,12)8-6-4-3-5-7(8)9(10)11/h3-6H,1-2H3,(H,10,11)

Isomere SMILES

CP(=O)(C)C1=CC=CC=C1C(=O)O

Alternative CAS-Nummer

79317-57-0

PubChem CID

563163

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acids
• Alternative Parents: Benzoyl derivatives Phenylphosphines and derivatives Organophosphine oxides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoic acid - Benzoyl - Phenylphosphine - Organophosphine oxide - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organophosphorus compound - Organooxygen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 198.160 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 198.045 Da
• Monoisotopic Mass: 198.045 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 243.000
• 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 as a bioassay reagent. No validated protocols for WB, IHC, IF, or flow cytometry are associated with this small-molecule building block.

For chemical applications, see Reaction Conditions and Synthetic Utility for general procedural guidance. Always optimize on small scale before larger preparations.

Biological Roles

This compound is a synthetic aryl carboxylic acid bearing a dimethylphosphoryl substituent and is intended for research and laboratory chemistry.

• Known endogenous role: none (not a natural metabolite).
• Biochemical interactions: aryl phosphine oxides can engage in hydrogen bonding via the P=O oxygen and can chelate to metal centers; however, no specific biological pathway involvement is established for this structure (literature).
• Use context: primarily as a chemical building block, ligand precursor, or coordination probe in materials/coordination chemistry. Any biological testing must be conducted under appropriate research approvals.

No medical or clinical claims are made. For research use only (per Product Data).

Buffer Applications

Not typically used as a buffering agent. As a monofunctional carboxylic acid without a conjugate base pair tailored for buffering near physiological ranges, it is not part of standard laboratory buffer systems.

• If aqueous work is required, the compound’s carboxylate salt can be formed with bases (NaHCO3, Na2CO3) to increase solubility for extraction or processing, but this is not a true buffer system.

Refer instead to the Solvent Selection, Reaction & Applications, and Synthetic Utility sections for relevant usage guidance.

Green Alternatives

This product is a solid organic building block rather than a process solvent. Green-chemistry considerations primarily concern choice of reaction media and coupling systems when using it.

Greener choices around common operations (literature guidance):

• Amidation/esterification media: replace DMF/DCM with Me-THF, CPME, 2-propanol, or water-enabled systems when feasible. Use catalytic DMAP and water-soluble carbodiimides (e.g., EDC) to minimize urea waste vs DCC.
• Acid activation: consider T3P (propylphosphonic anhydride in EtOAc) as a lower-toxicity, easier-to-work-up alternative to oxalyl chloride or SOCl2, noting different impurity profiles.
• Reduction of phosphine oxide: select milder hydrosilane systems (PMHS, a polymeric byproduct of silicone industry) with catalytic Ti(OiPr)4 instead of stoichiometric chlorosilanes; balance with workup complexity and potential Ti residues.

Small comparison (general):

• DMF vs Me-THF: Me-THF offers lower toxicity, partial bio-derived content, easier separation; however, polarity may be insufficient for some couplings—solubility testing is required.
• DCM vs EtOAc: EtOAc is less hazardous and more biodegradable; may require temperature control due to higher boiling point and different solvation.

Waste minimization:

• Run couplings at higher concentration to reduce solvent volume.
• Favor catalytic activation strategies where possible and recover metals if used. Always follow local regulations for disposal of phosphorus-containing residues.

Pharmaceutical Uses

Not an approved excipient and not intended for clinical use. No pharmacopeial monograph is indicated.

Potential formulation-relevant notes in a research/manufacturing context (general):

• As a polar aromatic acid, it could serve as an intermediate in the synthesis of ligands or API building blocks, but it is not itself a formulated excipient.
• The P=O group can coordinate metals; avoid unintended carryover into GMP streams unless fully justified and controlled.

For regulated applications, obtain detailed impurity profiles and residual solvent/metals data from the CoA/Spec Sheet. Use is restricted to research and development only (per Product Data).

Physical Properties

Item-specific physicochemical specifications (bp, mp, density, refractive index, elemental/metals, UV cutoffs): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for this class of compound (for method planning only):

• Physical state: typically a crystalline solid for aryl carboxylic acids bearing phosphine oxide groups (literature). Exact appearance for this SKU: Not specified.
• Acidic character: benzoic-acid–like acidity; ortho electron-withdrawing P=O may slightly enhance acidity relative to benzoic acid (pKa benzoic acid ≈ 4.20, literature). For this specific compound, expected pKa (carboxyl): ~3.8–4.3 (literature/analogs); confirm experimentally for your system.
• Polarity: high due to carboxylic acid and P=O; good H-bonding capability (acceptor: P=O; donor: –CO2H).
• Solubility profile (qualitative, literature):
  • Good: polar aprotic organics (DMSO, DMF, NMP), alcohols (MeOH, EtOH) upon gentle warming or as salts.
  • Moderate: acetone/EtOAc; lower in nonpolar hydrocarbons (hexanes, heptane).
  • Aqueous: low as free acid; increases on basification to the carboxylate salt.

Do not treat any of the above as product specifications. For validated values used in regulated environments, consult the item’s CoA/Spec Sheet and SDS.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Storage: Room temperature (per Product Data). Shipped under normal conditions.

Interpretation and implications:

• In absence of a stated analytical grade (e.g., AR, HPLC, anhydrous), treat this material as a research-grade reagent suitable for general synthetic use. If low UV background, ultra-trace metals, water content, or specific residual-solvent limits are critical, request the current CoA/Spec Sheet.
• Typical quality controls for this class may include NMR (1H, 13C, 31P), HPLC/GC purity, melting range (if solid), and water content (KF). None are item-specific unless reported on the CoA/Spec Sheet.
• Stabilizers/inhibitors: None indicated. Phosphine oxides are inherently stable to air/oxidation; no antioxidant normally required.

Recommendations for critical applications:

• Chromatography-sensitive uses (UV detection ≤220 nm), organometallic catalysis (phosphine formation), or structure-based studies should verify purity by NMR including 31P and assess residual metals/halides as needed (Not specified for this item; refer to CoA/Spec Sheet for any limits).

Reaction and Applications

As a bifunctional aryl building block, 2-(Dimethylphosphoryl)benzoic acid provides orthogonal chemistry at the carboxyl carbon and at the aryl–P(=O)Me2 moiety.

• Carboxylate derivatization:
  • Amide formation: standard peptide-coupling reagents (EDC·HCl, HATU, PyBOP) give amides that retain the P=O functionality. Use mild bases (DIPEA) and minimize excess nucleophiles that might strongly coordinate P=O.
  • Ester formation: Fischer esterification (alcohol/H+, reflux), Steglich esterification (DCC or EDC + DMAP, DCM) afford esters useful as protecting groups or for solubility tuning.
  • Acid chloride: SOCl2 or (COCl)2 with DMF catalyst (literature) enables subsequent acylations; ensure anhydrous conditions and control exotherm.
• Phosphine-oxide–centered transformations:
  • Reduction to aryl dimethylphosphine ligands: trichlorosilane/Et3N in toluene or dichloromethane, or PMHS/Ti(OiPr)4 systems (literature) reduce ArP(=O)Me2 → ArPMe2. The resulting secondary/tertiary phosphine can be isolated as its borane complex (BH3·THF) for air-stable handling.
  • Oxidation state stability: P=O is robust to most coupling conditions; it can act as a directing/chelating site in metalation/C–H activation chemistry (literature), sometimes enabling regioselective transformations on the ring.
• Orthogonal functionality and ligand design:
  • The ortho juxtaposition of –CO2H and P=O supports intramolecular H-bonding and bidentate chelation to metals (e.g., Zr/Hf, lanthanides) for materials and coordination studies.
  • The aryl–P(=O)Me2 motif is a precursor in the synthesis of tailored phosphine ligands for cross-coupling catalysis after reduction and subsequent functional modification.

Applications are for research use only (per Product Data). Validate conditions at small scale before scale-up.

Reaction Conditions

The following conditions are general literature guidance for this class of substrates; they are not item-specific specifications.

• Amide coupling (EDC/HOBt or HATU):

  • Solvent: DMF or DCM (anhydrous); base: DIPEA (2–3 equiv).
  • Stoichiometry: acid (1.0 equiv), amine (1.1–1.5 equiv), coupling reagent (1.1–1.5 equiv).
  • Temperature/time: 0–25 °C, 2–16 h. Typical isolated yields: 70–95% for unhindered partners (literature).

• Steglich esterification (DCC/DMAP):

  • Solvent: DCM or DCM/DMF.
  • Additives: DMAP (0.1 equiv). DCC (1.2 equiv).
  • 0 °C to rt, 4–18 h; filter urea byproduct and purify.

• Acid chloride formation:

  • Reagents: SOCl2 (3–5 equiv) or (COCl)2 (2–3 equiv) + catalytic DMF.
  • Solvent: DCM or neat; reflux SOCl2 or 0–25 °C for (COCl)2.
  • Notes: exclude moisture; vent HCl/ SO2/ CO gases appropriately.

• Reduction of aryl dimethylphosphine oxide to aryl dimethylphosphine (literature examples):

  • HSiCl3 (4–6 equiv), Et3N (6–8 equiv), DCM or toluene, 0 °C → rt, 2–6 h; quench cautiously, isolate phosphine as BH3 adduct if needed.
  • PMHS (3–5 equiv) + Ti(OiPr)4 (10–20 mol%) in toluene, 80–110 °C, 6–24 h.

• NMR characterization:

  • 31P{1H} typically shows a singlet for ArP(=O)Me2 in the +25 to +45 ppm range (relative to 85% H3PO4) and shifts downfield/upfield modestly with hydrogen bonding (literature).

Safety and Handling

Authoritative safety information must be taken from the product SDS. The following are general considerations for aryl carboxylic acids bearing phosphine oxide groups.

• GHS classification, pictograms, signal word, H/P statements: Not specified for this item; refer to SDS.
• Likely hazards (general): carboxylic acids are typically irritants to skin/eyes; dust may irritate respiratory tract. Phosphine oxides are generally of low volatility and comparatively low acute toxicity (literature), but avoid ingestion and inhalation of dust.
• PPE: lab coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile). Weigh in a fume hood to avoid dust exposure.
• Handling tips:
  • Avoid contact with strong bases and oxidizers. Formation of carboxylate salts at high pH can increase solubility and migration.
  • Hygroscopicity: not typically pronounced for aryl acids, but keep container tightly closed to prevent moisture uptake and contamination.
• First aid (general):
  • Eye/skin contact: rinse with water for 15 minutes, remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; seek medical attention if symptoms develop.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Fire safety: combustible organic solid; use CO2, dry chemical, or foam. Product is expected to be thermally stable relative to phosphines because it is an oxide.
• Spill response: avoid dust generation; collect mechanically; wash residue with suitable solvent while controlling for compatibility and waste regulations.

Solvent Selection

This compound is a polar, hydrogen-bonding solid with both an acidic carboxyl and a strongly polar P=O group.

• Polarity/miscibility (general, literature):
  • Highly soluble in polar aprotic solvents (DMSO, DMF, NMP) and in alcohols with warming.
  • Sparingly soluble in nonpolar solvents (hexanes, toluene) as free acid; solubility improves upon conversion to esters or salts.
  • Aqueous solubility is limited at neutral pH; increases markedly in basic aqueous media as the carboxylate salt.
• Dielectric constants (solvent context, literature): DMSO ≈ 47, DMF ≈ 38, MeOH ≈ 33, EtOAc ≈ 6. These support dissolution of polar organics via strong dipole and H-bonding interactions.

When to choose specific solvents (practical guidance):

• NMR: DMSO-d6 or CD3OD typically give sharp 31P and aromatic 1H signals; slight intramolecular H-bonding may shift –CO2H and P=O resonances.
• Coupling/activation of the acid: DMF, DCM, or MeCN are common media for EDC/HOBt, HATU, or mixed anhydride routes; base choice (DIPEA, collidine) should balance minimizing P=O coordination.
• Esterification: MeOH/EtOH under Fischer conditions; for Steglich esterification use DCM/DMF with DMAP and DCC/EDC.
• Purification: Silica gel chromatography using EtOAc/hexanes or MeOH/CH2Cl2 gradients; note that strong adsorption may occur due to –CO2H and P=O—add a small % of acetic acid or NH3 to mobile phase to manage tailing.

For moisture- or base-sensitive transformations (e.g., acid chlorides), use dry, oxygen-free solvents.

Storage and Reconstitution

• Storage conditions (per Product Data): Room temperature. Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to moisture and strong bases/acids during storage.
• Shipping: Shipped under normal conditions (per Product Data).

Reconstitution and use (general guidance):

• Dissolution: For stock solutions, use dry polar solvents such as DMSO, DMF, or MeOH. Warm gently and sonicate if needed. For aqueous workflows, dissolve by first preparing the sodium or potassium carboxylate salt (add equimolar NaHCO3/Na2CO3), then adjust pH as required.
• Concentration ranges: prepare 0.05–0.5 M stock solutions in DMSO/DMF for synthetic operations; store aliquots to minimize freeze–thaw of solutions.
• Stability notes: Phosphine oxides are air-stable; the carboxylic acid is stable under neutral conditions. Avoid strong bases for extended periods to prevent undesired reactions (e.g., ester hydrolysis if present) and potential metal-catalyzed side reactions due to P=O coordination.
• Solid handling: If caking occurs, gently break up under dry conditions. Desiccation can help maintain consistent weighing.

For any item-specific stability or solution shelf-life limits, consult the current CoA/Spec Sheet and SDS.

Structure and Identity

A bifunctional aromatic building block combining a benzoic acid (carboxylic acid) with an ortho-dimethylphosphoryl (aryl–P(=O)Me2) substituent.

• Product name: 2-(Dimethylphosphoryl)benzoic acid (o-(Dimethylphosphoryl)benzoic acid)
• CAS: 79317-57-0
• PubChem CID: 563163 (literature identifier)
• InChIKey (from Product Data): 467773
• 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 description):

• Aromatic benzene ring bearing two ortho-adjacent substituents: a carboxylic acid group (–C(=O)OH) and a dimethylphosphoryl group (–P(=O)(CH3)2) directly bonded to the ring carbon.
• Functional groups: carboxylic acid (acidic, H-bond donor/acceptor), tertiary phosphine oxide (strongly polar P=O, H-bond acceptor, Lewis-basic oxygen), aryl C–P bond.
• Stereochemistry: none (achiral; no stereogenic centers).
• 2D structure in words: a benzene ring where adjacent positions carry (i) a benzoic acid function and (ii) a dimethylphosphoryl substituent; remaining ring positions are unsubstituted hydrogens.

Notes:

• The ortho arrangement enables intramolecular H-bonding between –CO2H and P=O in many aryl phosphine oxides (literature), potentially influencing conformation and acidity.

Synthetic Utility

Key reactive sites and transformations:

• Carboxylic acid handle:

  • Conversion to acid chlorides (SOCl2 or (COCl)2/DMF catalyst) for acylation of nucleophiles.
  • Formation of amides and esters via EDC/HOBt, HATU, or T3P-mediated couplings; Steglich esterification (DCC/DMAP) in DCM or DMF.
  • Decarboxylative strategies (literature) may be explored under photoredox or silver-mediated conditions to access aryl radicals adjacent to a P=O directing group.

• Aryl dimethylphosphine oxide:

  • Robust to many oxidative and basic conditions; serves as a directing/coordination site in Pd/Ir/Ru-catalyzed C–H activation (literature), enabling regioselective functionalizations on related scaffolds.
  • Reduction to aryl dimethylphosphine (ArPMe2) using HSiCl3/Et3N (DCM/toluene), or PMHS with Ti catalysts. The resulting phosphine can be trapped as a borane adduct (ArPMe2·BH3) for air-stable handling and later deprotected.
  • Further elaboration: oxidation state toggling (P(III)↔P(V)) for ligand tuning; quaternization at phosphorus is not applicable here because phosphorus is fully substituted (P(V)).

Strategic value:

• Orthogonal functionalization permits sequential synthesis: first derivatize the acid (amide/ester), then reduce P=O to obtain a ligand precursor embedded in a functionalized arene, or vice versa.
• The ortho relationship of –CO2H and P=O can assist intramolecular H-bonding, sometimes improving crystallinity and facilitating purification (literature observation).

Target Specificity

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

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 79317-57-0. InChIKey ZVUKMPRMHHHNQW-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.