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Diethylbenzylphosphonat

diethyl benzylphosphonate Struktur
1080-32-6
CAS-Nr.
1080-32-6
Bezeichnung:
Diethylbenzylphosphonat
Englisch Name:
diethyl benzylphosphonate
Synonyma:
BENV-006;NSC 62294;Diethylbenzylphosphonat;DIETHYL BENZOPHOSPHONATE;DIETHYLBENZYLPHOSPHORATE;DIETHYL BENZYLPHOSPHONATE;DIETHOXY BENZYLPHOSPHONATE;Diethylα-toluenephosphonate;Diethyl phosphonate, benzyl-;diethyl à-toluenephosphonate
CBNumber:
CB5696730
Summenformel:
C11H17O3P
Molgewicht:
228.22
MOL-Datei:
1080-32-6.mol

Diethylbenzylphosphonat 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
Wasserl?slichkeit
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
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
R-S?tze: 36/38-36/37/38
S-S?tze: 24/25-37-26
WGK Germany  3
RTECS-Nr. SZ6600000
TSCA  Yes
HS Code  29319090
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.
P405 Unter Verschluss aufbewahren.

Diethylbenzylphosphonat Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R36/38:Reizt die Augen und die Haut.

S-S?tze Betriebsanweisung:

S24/25:Berührung mit den Augen und der Haut vermeiden.

Chemische Eigenschaften

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

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.

Diethylbenzylphosphonat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Diethylbenzylphosphonat Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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1080-32-6(Diethylbenzylphosphonat)Verwandte Suche:


  • (phenylmethyl)-phosphonicacidiethylester
  • benzyl-phosphonicacidiethylester
  • Benzylphosphonsαurediethylester
  • Diethoxyphosphonomethylbenzene
  • Diethyl phosphonate, benzyl-
  • DIETHYL BENZOPHOSPHONATE
  • Phenylmethanephosphonic acid diethyl ester
  • Diethylbenzylphosphonate, 99 %
  • Benzylphosphonic acid diethyl
  • NSC 62294
  • Diethyl benzylphosphonate, 99% 25GR
  • BENZYLPHOSPHONIC ACID DIETHYL ESTER
  • DIETHYL BENZYLPHOSPHONATE
  • DIETHOXY BENZYLPHOSPHONATE
  • Benzylphosphonic acid diethyl ester~Diethyl alpha-toluenephosphonate
  • diethyl à-toluenephosphonate
  • Diethylbenzylphosphonat
  • Diethylα-toluenephosphonate
  • Phenylmethanphosphonsαurediethylester
  • Phosphonic acid, benzyl-, diethyl ester
  • Phosphonicacid,(phenylmethyl)-,diethylester
  • BENZYLOPHOSPHONICACID,DIETHYLESTER
  • DIETHYLBENZYLPHOSPHORATE
  • BENV-006
  • Diethyl Benzylphosphonate >
  • Phosphonic acid, P-(phenylmethyl)-, diethyl ester
  • diethoxyphosphorylmethylbenzene
  • Diethyl P-(phenylmethyl)phosphonate
  • 1080-32-6
  • C6H5CH2POOC2H52
  • C11H17O3P
  • Synthetic Reagents
  • Olefination
  • C-C Bond Formation
  • Wittig & Horner-Emmons Reaction
  • Horner-Emmons Reaction
  • Horner-Wadsworth-Emmons Reagents
  • Horner-Emmons Reaction
  • Synthetic Organic Chemistry
  • Wittig & Horner-Emmons Reaction
  • C-C Bond Formation
  • Horner-Wadsworth-Emmons Reagents
  • Olefination
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