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ChemicalBook--->CAS DataBase List--->1067-87-4

1067-87-4

1067-87-4 Structure

1067-87-4 Structure
IdentificationMore
[Name]

DIETHYL ALLYLPHOSPHONATE
[CAS]

1067-87-4
[Synonyms]

ALLYLPHOSPHONIC ACID DIETHYL ESTER
AURORA KA-1466
DIETHYL (1-PROPENYL)PHOSPHONATE
DIETHYL-(2-PROPENYL)-PHOSPHONAT
DIETHYL(2-PROPENYL)PHOSPHONATE
DIETHYL-(ALLYLPHOSPHONAT)
DIETHYL ALLYLPHOSPHONATE
DIETHYL(PROP-1(E)-ENYL)PHOSPHONATE
DIETHYL(PROP-2-(E)-ENYL)PHOSPHONATE
Diethylallylphosphonate, 97 %
Diethyl allylphosphonate, 95+%
(2-Propenyl)phosphonic acid diethyl ester
2-Propenylphosphonic acid diethyl
Allylphosphonic acid diethyl
[EINECS(EC#)]

619-646-5
[Molecular Formula]

C7H15O3P
[MDL Number]

MFCD00015134
[Molecular Weight]

178.17
[MOL File]

1067-87-4.mol
Chemical PropertiesBack Directory
[Appearance]

clear colorless liquid
[Boiling point ]

46 °C/0.35 mmHg (lit.)
[bulk density]

1.022g/mL
[density ]

1,035 g/cm3
[vapor pressure ]

55.2Pa at 25℃
[refractive index ]

n20/D 1.4340(lit.)
[Fp ]

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 DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[HS Code ]

29319090
Hazard InformationBack Directory
[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.
reaction of 2 with dimethyl vinylphosphonate (3a) and diethyl allylphosphonate
[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.
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Diethyl allylphosphonate, 97%(1067-87-4)
[Alfa Aesar]

Diethyl allylphosphonate, 96%(1067-87-4)
[Sigma Aldrich]

1067-87-4(sigmaaldrich)
[TCI AMERICA]

Diethyl Allylphosphonate,>95.0%(GC)(1067-87-4)
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