Diethyl allylphosphonate Chemical Properties

Boiling point:

46 °C/0.35 mmHg (lit.)

Density 

1,035 g/cm³

bulk density

1.022g/mL

vapor pressure 

55.2Pa at 25℃

refractive index 

n20/D 1.4340(lit.)

Flash point:

224 °F

form 

Liquid

color 

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

Surface tension

56.4-60.9mN/m at 1g/L and 19℃

CAS DataBase Reference

1067-87-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diethyl allylphosphonate Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

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

Reactions

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

References

[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? MITU?A 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(1067-87-4)Related Product Information

• Diethyl allylmalonate
• 1-allylhydrazine hydrochloride
• ALLYLDIPHENYLPHOSPHINE
• Allyl methyl carbonate
• ALLYLDIPHENYLPHOSPHINE OXIDE
• Dimethyl allylmalonate
• Allyl Benzyl Ether
• Allylbenzene
• ALLYLUREA
• ALLYL PHENYL SULFIDE
• Allylthiourea
• ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II)
• ALLYL METHYL ETHER
• 2-Allyloxyethanol
• ALLYL IODIDE
• Allylboronic acid pinacol ester
• Allylamine hydrochloride
• TRIETHYL 4-PHOSPHONOCROTONATE