Ethyl (chloromethyl)(methyl)phosphinate - ≥95% , CAS No.110838-42-1

CAS: 110838-42-1 Cat. No.: E955140 Formula: C₄H₁₀ClO₂P Peso molecolare: 156.550 Numero EC: 823-519-1

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CCOP(=O)(C)CCl

IUPAC Name

1-[chloromethyl(methyl)phosphoryl]oxyethane

InChIKey

TTXWIKOQNODHCO-UHFFFAOYSA-N

INCHI

1S/C4H10ClO2P/c1-3-7-8(2,6)4-5/h3-4H2,1-2H3

Peso molecolare

156.550

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organophosphorus compounds
    • Classe Organophosphinic acids and derivatives
      • Subclass Phosphinic acid esters

• Kingdom: Organic compounds
• Superclass: Organophosphorus compounds
• Classe: Organophosphinic acids and derivatives
• Subclass: Phosphinic acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphinic acid esters
• Alternative Parents: Organooxygen compounds Organochlorides Organic oxides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Phosphinic acid ester - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phosphinic acid esters. These are compounds containing a phosphinic acid ester 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

Proprietà chimiche e fisiche

• Peso molecolare: 156.550 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 156.011 Da
• Monoisotopic Mass: 156.011 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 104.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 biological assay protocols (WB, IHC, IF, FC, etc.) apply to this small-molecule reagent. For synthetic applications, see the Reaction Conditions and Application notes provided. Always adjust stoichiometry, temperature, and solvent to your specific nucleophile/catalyst system and confirm by TLC/GC/HPLC/LC–MS.

Biological Roles

This product is a synthetic organophosphorus building block and does not have established endogenous biological roles.

• General notes (context only, not product-specific):

  • Phosphinate esters are analogs of phosphonate/phosphate motifs but, as esters, are typically not bioactive without specific design. Hydrolysis yields phosphinic acids, which can act as isosteres of carboxylic or phosphonic acids in medicinal chemistry discovery; any such use remains research-only and outside the scope of product claims.
  • No known participation in metabolic pathways as a natural metabolite.

• Biosafety:

  • Handle solely for in vitro/in vivo laboratory chemistry. No food, cosmetic, or clinical applications. Adhere to institutional approvals for any biological handling.

Item-specific biological activity data: Not specified for this item; refer to literature if designing biochemical probes from derived structures.

Buffer Applications

Not typically applicable. Ethyl (chloromethyl)(methyl)phosphinate is an organophosphorus ester used as a synthetic building block, not as a buffering agent. For experimental planning, refer instead to the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections.

Green Alternatives

• Solvent choices:

  • Prefer ethyl acetate, 2-MeTHF, or cyclopentyl methyl ether (CPME) over chlorinated solvents when feasible. These greener solvents can support SN2 and substitution chemistry at –CH2Cl while improving EHS profiles.

• Comparison (general guidance): | Parameter | DCM | MeCN | EtOAc | 2-MeTHF | |---|---|---|---|---| | Polarity (relative) | Moderate | High | Moderate | Moderate | | Boiling point | Low (40 °C) | 82 °C | 77 °C | 80 °C | | EHS profile | Halogenated | Acceptable | Preferred | Preferred | | SN2 rates | Good | Often best | Good | Good |

• Reagents and conditions:

  • Where classical protocols call for DMF/DMSO, consider MeCN or propylene carbonate as greener high-permittivity options if compatible with nucleophile/catalyst.
  • For workup, replace brine-heavy washes with minimal aqueous buffers and solid-supported scavengers to reduce wastewater.

• Waste minimization:

  • Design substitutions to be high atom-economy (e.g., azide displacement followed by Staudinger/ligation pathways) and use catalytic phase-transfer agents to reduce excess nucleophile.

• Item-specific eco-metrics (E-factors, energy intensity): Not specified for this item; evaluate per process.

Pharmaceutical Uses

• This product is intended for research use only.
• No pharmacopeial status, excipient role, or formulation use is provided for this item.
• General context (non-product-specific): Organophosphorus esters and their acids can serve as intermediates in discovery chemistry to explore phosphorus-containing bioisosteres; however, any clinical or therapeutic claims are explicitly excluded. If pursuing GMP or formulation work, source appropriate grade and regulatory documentation — this listing does not provide them.

Physical Properties

• Item-specific specifications (grade-dependent values such as water, metals, peroxide, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (non-spec, for context):

  • State at room temperature: Typically a colorless to pale liquid for low-mass phosphinate esters; verify on receipt.
  • Approximate relative polarity: Moderate due to P=O and P–O–Et functionality; significantly more polar than simple chlorinated alkanes.
  • Solubility: Expected to be miscible with many polar aprotic organic solvents (e.g., dichloromethane, acetonitrile, THF, ethyl acetate) and limited solubility in water due to ester character; possible slow hydrolysis in aqueous basic media.
  • Density, refractive index, boiling point, melting point, logP, pKa: Not specified for this item; consult CoA/SDS or primary literature for closely related phosphinate esters. Phosphinate P–OH conjugate acids typically have pKa1 ~1–2 and the P-centered acids pKa2 ~6–8 (literature, for free acids; esters do not display these equilibria).

• Practical notes (general):

  • Moisture sensitivity: Phosphinate esters are generally stable, but prolonged exposure to strong base or strong acid can promote hydrolysis or alcoholysis.
  • Thermal behavior: Avoid unnecessary heating until a verified boiling point/thermal profile is obtained from the CoA/SDS.

Quality and Grades

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

• General notes for this class of materials:

  • Research-grade phosphinate esters are typically provided with purity suitable for synthetic applications. If using in sensitive catalysis (e.g., cross-coupling), consider verifying trace metal and water content via CoA and, if critical, re-purify or dry prior to use.
  • Stabilizers: Not specified for this item. Many phosphinate esters are supplied neat without stabilizers; if any stabilizer is used, it will be listed on the CoA.

• What to check on receipt:

  • Purity method (GC, HPLC, NMR) and reported assay.
  • Water content (Karl Fischer) if relevant to moisture-sensitive reactions.
  • Residual solvents and halide content if the chloromethyl group’s reactivity is critical.

• Fit for purpose:

  • For routine organic synthesis or as a P-reagent in method development, research grade is generally appropriate.
  • For analytical applications (e.g., quantitative reference), verify assay and impurity profile or request higher-grade material if available.

Reaction and Applications

• Functional profile:

  • Phosphinate ester (P=O with P–OEt) bearing methyl and chloromethyl P–C bonds. The chloromethyl substituent enables SN2 substitution with soft to hard nucleophiles, furnishing –CH2–Nu derivatives tethered to phosphorus.

• Representative transformations (literature/general):

  • Nucleophilic substitution: Halide → azide, thiolate, alkoxide, amine under SN2 conditions (MeCN, DMF; 0–50 °C). Useful for installing handles for further elaboration or introducing functionality adjacent to the P center.
  • Reduction/dehalogenation: Hydrogenolysis or radical-based reduction of –CH2Cl to –CH3 under mild conditions.
  • Oxidation or functional group interconversions at the –CH2– site (e.g., conversion to alcohols via substitution then oxidation to aldehydes/acids if desired downstream).
  • Use as a phosphorus source: Phosphinate esters can engage in P–C bond forming reactions (e.g., Hirao-type couplings typically employ dialkyl phosphites/phosphonates; some protocols extend to phosphinates under modified conditions).

• Application domains:

  • Synthesis of P-containing ligands, pro-ligands, or building blocks for materials/coordination chemistry.
  • Preparation of functionalized phosphinate esters as intermediates in organophosphorus chemistry, including derivatives useful in flame-retardant, extractant, or surface-modifying motifs (research context).

• Practical tips:

  • Control moisture and base strength to minimize ester cleavage.
  • For SN2 at –CH2Cl, choose solvent/nucleophile pairing to favor substitution over elimination; use phase-transfer catalysis for heterogeneous systems.

Reaction Conditions

The following are literature-style general conditions for functional group classes analogous to this reagent; they are not product specifications.

• SN2 substitution at –CH2Cl:

  • Nucleophiles: NaN3, KSAc, NaOMe/RO−, secondary amines, thiolates.
  • Solvents: MeCN, DMF, DMSO, 2-MeTHF.
  • Base: Na2CO3, K2CO3, DIPEA (as appropriate to nucleophile).
  • Temperature: 0–60 °C; monitor to control exotherm and suppress elimination.
  • Time: 1–16 h depending on nucleophile and solvent.
  • Notes: Employ dry conditions; add nucleophile slowly. Phase-transfer catalysis (e.g., TBAB) can accelerate heterogeneous substitutions.

• Hydrolysis/transesterification (if needed downstream):

  • Acidic methanolysis/ethanolysis at ambient to 50 °C with catalytic HCl/H2SO4; or basic NaOMe/NaOEt under carefully controlled, low-temperature conditions.
  • Caution: Overexposure to base can lead to decomposition.

• Reductive dechlorination:

  • Catalytic hydrogenation (Pd/C, 1–3 bar H2, RT–40 °C) or radical-based conditions (e.g., tributyltin hydride alternatives) under photoredox catalysis.

• Workup/purification:

  • Quench reactive nucleophiles cautiously; extract with non-basic, non-aqueous systems where possible. Use buffered aqueous washes to minimize hydrolysis; dry over MgSO4/Na2SO4 and purify quickly on neutral or slightly acidic silica.

Safety and Handling

• Item-specific (from Product Data):

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General GHS considerations for organophosphorus phosphinate esters (literature/general guidance):

  • May cause eye/skin irritation and respiratory tract irritation. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
  • Chloromethyl functionality can be irritating; handle in a fume hood.

• PPE and engineering controls:

  • Use chemical splash goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Employ fume hood or local exhaust ventilation.
  • Avoid contact with strong bases/acids and strong nucleophiles that may induce decomposition or substitution.

• Incompatibilities and reactivity (general):

  • Strong bases/acids can catalyze hydrolysis/transesterification.
  • Strong nucleophiles can displace chloride on the chloromethyl group (exothermic SN2 possible). Add nucleophiles slowly with temperature control.

• First aid (general, defer to SDS for authoritative guidance):

  • Eye/skin contact: Rinse with water for 15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Waste: Collect organophosphorus waste in halogenated-organic waste streams per institutional and local regulations.

Solvent Selection

This compound is a moderately polar organophosphorus ester with a reactive chloromethyl substituent.

• General miscibility profile (literature-based):

  • Good solubility in polar aprotic media (DCM, THF, acetonitrile, acetone, ethyl acetate).
  • Limited solubility expected in alkanes; modest in toluene.
  • Hydrolysis/transesterification possible in aqueous strong acid/base; avoid prolonged exposure to aqueous media.

• Selection tips by use-case:

  • Nucleophilic substitution at chloromethyl: Use dipolar aprotic solvents (e.g., DMF, DMSO, MeCN) to enhance SN2 rates; manage exotherm.
  • Transition-metal-catalyzed coupling using P(V) reagents (if applicable): THF, dioxane, toluene, or MeCN commonly employed depending on catalyst system.
  • Purification: DCM/EtOAc/hexanes mixtures often provide good chromatographic performance; monitor for hydrolysis on basic silica.

• Comparison (general):

  • THF vs MeCN: THF offers broader solubility for organics and compatibility with many catalysts; MeCN provides higher polarity and can accelerate bimolecular substitutions.
  • DCM vs EtOAc: DCM maximizes solubility and volatility; EtOAc is a greener alternative with higher polarity and safer profile.

• Item-specific solvent specs (UV cutoff, water content limits): Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage (from Product Data): Room temperature.
• Shipping: Not specified for this item; typical ambient shipment is suitable for stable organophosphorus esters unless otherwise indicated.
• Container: Store tightly closed in a dry, inert atmosphere if possible (e.g., under nitrogen/argon) to minimize hydrolysis and oxidation.
• Stability considerations (general):
  • Protect from moisture and strong acids/bases. Avoid prolonged exposure to elevated temperatures.
  • If long-term storage is anticipated, consider refrigerating (2–8 °C) as a conservative practice unless crystallization or viscosity becomes problematic; equilibrate to room temperature before opening to prevent condensation.
• Reconstitution: Supplied neat unless otherwise stated. If preparing stock solutions, use dry, oxygen-free solvents (e.g., anhydrous MeCN, DCM, or THF). Store solutions in sealed glass under inert gas at low temperature; prepare fresh for moisture-sensitive transformations.
• Freeze–thaw: Not typically applicable to neat liquids. If stored as a solution, avoid repeated freeze–thaw by aliquoting.
• On receipt: Inspect for clarity/color; any turbidity or acidic odor may indicate hydrolysis—check by 31P/1H NMR before critical use.

Structure and Identity

Ethyl (chloromethyl)(methyl)phosphinate is an organophosphorus phosphinate ester featuring a P(V)=O center, one alkoxy substituent, and two P–C alkyl substituents (methyl and chloromethyl).

• Item-specific (from Product Data):

  • CAS: 110838-42-1
  • CID: 10630760
  • InChIKey: 349908 (as provided; atypical format length — verify against CoA/SDS)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (non-spec, for context):

  • Expected structural motif: EtO–P(=O)(CH3)(CH2Cl) — an ethyl phosphinate ester with methyl and chloromethyl substituents on phosphorus.
  • Functional groups: phosphoryl (P=O), phosphate ester (P–O–Et), two P–C alkyls (methyl, chloromethyl), benzylic-like chloromethyl C–Cl suitable for SN2.
  • Stereochemistry: None (achiral at P; P is tetracoordinate in a trigonal-bipyramidal resonance description around P=O but no stereogenic center here).
  • 2D description in words: A tetra-coordinated phosphorus doubly bonded to oxygen; single bonded to an ethoxy group, a methyl group, and a chloromethyl group.

• Molecular formula and molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation for the formula based on the name would be consistent with a small C4 framework bearing P, two O, and Cl; confirm on CoA.)

Synthetic Utility

• Building-block logic:

  • The molecule provides a P(V) phosphinate core with two P–C bonds (methyl and chloromethyl) and one P–O–ethyl ester. The chloromethyl moiety is a versatile handle for SN2 diversification, enabling installation of N-, O-, S-, or C-nucleophiles to furnish functionalized –CH2–X arms adjacent to phosphorus.

• Strategic transformations (literature/general):

  • Alkyl/aryl substitution at –CH2Cl with secondary amines or azide (followed by reduction) to build aminoalkyl-phosphinate derivatives.
  • Thiolate substitution to access thioether-functional phosphinates; useful as ligating motifs or for further oxidation to sulfoxides/sulfones.
  • Conversion to alcohols via acetate displacement/hydrolysis and subsequent oxidations, extending the homologation manifold from the P center.
  • Engagement in radical chemistry (e.g., halogen-atom transfer) to edit the –CH2– substituent under photochemical conditions.

• Retrosynthetic value:

  • Serves as a convergent entry to P-containing analogs of small molecules where a methylene spacer from P is required. The ethyl ester can later be transesterified or hydrolyzed (under controlled conditions) to adjust protecting group patterns at phosphorus.

• Compatibility considerations:

  • Avoid strong base in alcohol solvents to prevent transesterification.
  • Use neutral/almost-neutral silica for chromatography to minimize ester cleavage.

Target Specificity

Not applicable. This product is a small-molecule organophosphorus building block and is not an antibody, enzyme, or biological affinity reagent. No antigen/epitope specificity or species reactivity applies.