| Identification | More | [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 Properties | Back 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
| [storage temp. ]
2-8°C, stored under nitrogen | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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
| [REACH Registrations]
Active | [HS Code ]
29319090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back 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.
 | [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. |
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