Diethyl allylphosphonate

Bezeichnung:Diethyl allylphosphonate

CAS-Nr1067-87-4

Englisch Name:Diethyl allylphosphonate

CBNumberCB2385035

SummenformelC7H15O3P

Molgewicht178.17

MOL-Datei1067-87-4.mol

Diethyl allylphosphonate physikalisch-chemischer Eigenschaften

Siedepunkt	46 °C/0.35 mmHg (lit.)
chüttdichte	1.022g/mL
Dichte	1,035 g/cm³
Dampfdruck	55.2Pa at 25℃
Brechungsindex	n20/D 1.4340(lit.)
Flammpunkt	224 °F
storage temp.	2-8°C, stored under nitrogen
Aggregatzustand	Liquid
Farbe	Clear colorless
InChI	InChI=1S/C7H15O3P/c1-4-7-11(8,9-5-2)10-6-3/h4H,1,5-7H2,2-3H3
InChIKey	YPJHXRAHMUKXAE-UHFFFAOYSA-N
SMILES	P(CC=C)(=O)(OCC)OCC
LogP	1.33 at pH7
Oberflächenspannung	56.4-60.9mN/m at 1g/L and 19℃
CAS Datenbank	1067-87-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
HS Code	29319090
Speicherklasse	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

Diethyl allylphosphonate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
clear colorless liquid
Verwenden
Reactant for:
- Copolymerization of phosphonated allyl monomers and maleic anhydride
- Enantioselective synthesis of solamin type mono-THF acetogenins
- RCM reaction yielding oxaphospholene and oxaphosphinene heterocycles
- Synthesis of spongistatin 2 using Wittig coupling
- Stereoselective synthesis of pentacyclic furanosteroids
- Preparation of protected polyhydroxylated β -amino acid constitutents of microsclerodermins
Reaktionen
To a stirred solution of diethyl allylphosphonate (582.5 mg, 3.0 mmol, 1.5 equiv) in dry THF (25 mL) was added NaH (60% dispersion in mineral oil, 120 mg, 3.0 mmol, 1.5 equiv) portion wise under nitrogen atmosphere at 0°C. After 15 min, aryl/alkyl aldehyde 14a–x, 14z (2.0 mmol) in dry THF was added to the reaction mixture and stirred at 0°C until the completion (monitored by TLC) of reaction. It was then quenched with saturated aq. NH4Cl and the solution was extracted with EtOAc (2×20 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using petroleum ether/EtOAc (9:1, common for all compounds unless specified) as eluent to afford (E)-1-aryl/alkylbutadienes 7a–x, 7z.
The CM reaction of 2 with dimethyl vinylphosphonate (3a) and diethyl allylphosphonate (3b) under a classic thermal condition with 3 mol % of H-G II at 40 °C.
Synthesis Reference(s)
Synthetic Communications, 22, p. 2219, 1992 DOI: 10.1080/00397919208019075
Synthesis, p. 563, 1986 DOI: 10.1055/s-1986-31704
reaction suitability
reaction type: C-C Bond Formation
Einzelnachweise
[1] CHOUDHARY P, RANJAN R S, FERNANDES R. Cu-Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β-Chlorosulfones[J]. European Journal of Organic Chemistry, 2024, 28 1. DOI:10.1002/ejoc.202401077.
[2] SE MYEONG CHOI, JONG HYUN CHO* Direct Synthesis of Aryloxy Phosphonamidate Nucleotide Prodrugs Using the Cross Metathesis Assisted by Ultrasonic Irradiation[J]. Organic Letters, 2024, 26 23: 4841-4846. DOI:10.1021/acs.orglett.4c00094.
[3] ELIZABETH I. PARKINSON. Fosmidomycin biosynthesis diverges from related phosphonate natural products[J]. Nature chemical biology, 2019, 15 11: 1049-1056. DOI:10.1038/s41589-019-0343-1.
[4] PAWE MITUA C. W. Synthesis of a series of new racemic [2,3-bis(acyloxy)propyl]phosphonocholines[J]. Arkivoc, 2012, 2012 1. DOI:10.3998/ARK.5550190.0013.416.

Diethyl allylphosphonate Upstream-Materialien And Downstream Produkte

Diethyl allylphosphonate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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