Identification | More | [Name]
DIETHYL BENZYLPHOSPHONATE | [CAS]
1080-32-6 | [Synonyms]
BENZYLPHOSPHONIC ACID DIETHYL ESTER DIETHOXY BENZYLPHOSPHONATE DIETHYL BENZYLPHOSPHONATE (phenylmethyl)-phosphonicacidiethylester benzyl-phosphonicacidiethylester Benzylphosphonsαurediethylester Diethoxyphosphonomethylbenzene Diethyl phosphonate, benzyl- Diethylbenzylphosphonat Diethylα-toluenephosphonate Phenylmethanphosphonsαurediethylester Phosphonic acid, benzyl-, diethyl ester Phosphonicacid,(phenylmethyl)-,diethylester Benzylphosphonic acid diethyl ester~Diethyl alpha-toluenephosphonate diethyl à-toluenephosphonate BENZYLOPHOSPHONICACID,DIETHYLESTER DIETHYLBENZYLPHOSPHORATE DIETHYL BENZOPHOSPHONATE Phenylmethanephosphonic acid diethyl ester Diethylbenzylphosphonate, 99 % | [EINECS(EC#)]
214-097-4 | [Molecular Formula]
C11H17O3P | [MDL Number]
MFCD00009078 | [Molecular Weight]
228.22 | [MOL File]
1080-32-6.mol |
Safety Data | Back Directory | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
SZ6600000
| [TSCA ]
Yes | [HS Code ]
29319090 |
Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID | [Uses]
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
| [Uses]
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. | [Uses]
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 Horn | [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. |
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