Diethylbenzylphosphonat

Bezeichnung:Diethylbenzylphosphonat

CAS-Nr1080-32-6

Englisch Name:diethyl benzylphosphonate

CBNumberCB5696730

SummenformelC11H17O3P

Molgewicht228.22

MOL-Datei1080-32-6.mol

Synonyma

Diethylbenzylphosphonat

Diethylbenzylphosphonat physikalisch-chemischer Eigenschaften

Siedepunkt	106-108 °C1 mm Hg(lit.)
Dichte	1.095 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.497(lit.)
Flammpunkt	>230 °F
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	Liquid
Wichte	1.10
Farbe	Clear colorless to slightly yellow
Wasserlöslichkeit	Insoluble in water.
BRN	2580931
CAS Datenbank	1080-32-6(CAS DataBase Reference)
EPA chemische Informationen	Phosphonic acid, (phenylmethyl)-, diethyl ester (1080-32-6)

Sicherheit

R-Sätze:	36/38-36/37/38
S-Sätze:	24/25-37-26
WGK Germany	3
RTECS-Nr.	SZ6600000
TSCA	Yes
HS Code	29319090

Gefahreninformationscode (GHS)

diethyl benzylphosphonate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
Verwenden
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
Verwenden
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.
synthetische
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
Einzelnachweise
[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.

diethyl benzylphosphonate Upstream-Materialien And Downstream Produkte

Diethylbenzylphosphonat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1080-32-6, diethyl benzylphosphonate Verwandte Suche:

Send Inquriy