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HomeProduct name listdiethyl benzylphosphonate

diethyl benzylphosphonate

Synonym(s):(Diethoxyphosphonomethyl)benzene;Benzylphosphonic acid diethyl ester;NSC 62294

  • CAS NO.:1080-32-6
  • Empirical Formula: C11H17O3P
  • Molecular Weight: 228.22
  • MDL number: MFCD00009078
  • EINECS: 214-097-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-12-07 15:50:20
diethyl benzylphosphonate Structural

What is diethyl benzylphosphonate?

Chemical properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

The Uses of diethyl benzylphosphonate

Reactant for synthesis of:
    3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders
    Natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions
    Stilbenes via on-column oxidation of vicinal diols and Horner-Emmons reactions
    Inhibitors of teh Wnt pathway for colon cancer repression using Wadsworth-Emmons reactions
    Antimalarial drug analogs against P. falciparum

Reactant for:
Cyclization of aryl ethers, amines, and amides
Investigating the effects of functional groups on the performance of clue organic LEDs

The Uses of diethyl benzylphosphonate

Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs.

Preparation

Diethyl benzylphosphonate was synthesized according to the previously published procedure [1]. Benzylphosphonic acid (1 mmol, 172 mg) and triethyl orthoacetate (30 mmol, 5.5 mL) were mixed overnight at 90 °C. The completion of the reaction was monitored by 31P NMR. After the completion of the reaction, an excess of the orthoester was evaporated under reduced pressure. The crude product was purified via a short silica gel column (hexanes/ethyl acetate). The compound 1 was isolated as a transparent oil with 98% yield (0.98 mmol, 224 mg). 1H NMR (400 MHz, DMSO-d6) δ 7.39–7.14 (m, 5H), 3.94 (dq, JH-P = 7.9, JH-H = 7.0, 4H), 3.21 (d, JH-P = 21.6 Hz, 2H), 1.16 (t, JH-H = 7.0 Hz, 6H); 13C NMR (101 MHz, DMSO-d6) δ 132.3 (d, JC-P = 9.0 Hz), 129.7 (d, JC-P = 6.6 Hz), 128.2 (d, JC-P = 3.0 Hz), 126.4 (d, JC-P = 3.4 Hz), 61.3 (d, JC-P = 6.5 Hz), 32.3 (d, JC-P = 135.1 Hz), 16.1 (d, JC-P = 5.8 Hz); 31P NMR (162 MHz, DMSO-d6) δ 26.5. The NMR data are in accordance with those reported in literature [2].

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 1513, 1988 DOI: 10.1016/S0040-4039(00)80339-1
Synthesis, p. 222, 1981 DOI: 10.1055/s-1981-29393

References

[1] DAMIAN TRZEPIZUR. Selective Esterification of Phosphonic Acids.[J]. Molecules, 2021. DOI:10.3390/molecules26185637.
[2] PETER J. THORNTON. Nucleoside Phosphate and Phosphonate Prodrug Clinical Candidates[J]. Journal of Medicinal Chemistry, 2016, 59 23: 10400-10410. DOI:10.1021/acs.jmedchem.6b00523.
[3] GASTON LAVEN. ChemInform Abstract: Preparation of Benzylphosphonates via a Palladium(0)-Catalyzed Cross-Coupling of H-Phosphonate Diesters with Benzyl Halides. Synthetic and Mechanistic Studies.[J]. ChemInform, 2010, 41 40. DOI:10.1002/chin.201040191.
[4] ANNA BRODZKA. The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents.[J]. Molecules, 2022. DOI:10.3390/molecules27206865.

Properties of diethyl benzylphosphonate

Boiling point: 106-108 °C1 mm Hg(lit.)
Density  1.095 g/mL at 25 °C(lit.)
refractive index  n20/D 1.497(lit.)
Flash point: >230 °F
storage temp.  Sealed in dry,Room Temperature
form  Liquid
color  Clear colorless to slightly yellow
Specific Gravity 1.10
Water Solubility  Insoluble in water.
BRN  2580931
CAS DataBase Reference 1080-32-6(CAS DataBase Reference)
EPA Substance Registry System Phosphonic acid, (phenylmethyl)-, diethyl ester (1080-32-6)

Safety information for diethyl benzylphosphonate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for diethyl benzylphosphonate

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