Diethyl allylphosphonate
- Product Name
- Diethyl allylphosphonate
- CAS No.
- 1067-87-4
- Chemical Name
- Diethyl allylphosphonate
- Synonyms
- AURORA KA-1466;Diethyl Allylphosphote;DIETHYL ALLYLPHOSPHONATE;DIETHYL-(ALLYLPHOSPHONAT);DiethylAllylphosphonate>Allylphosphonic acid diethyl;Diethylallylphosphonate, 97 %;Diethyl allylphosphonate, 95+%;DIETHYL(2-PROPENYL)PHOSPHONATE;3-diethoxyphosphorylprop-1-ene
- CBNumber
- CB2385035
- Molecular Formula
- C7H15O3P
- Formula Weight
- 178.17
- MOL File
- 1067-87-4.mol
Diethyl allylphosphonate Property
- 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
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 565415
- Product name
- Diethyl allylphosphonate
- Purity
- 98%
- Packaging
- 5g
- Price
- $97.47
- Updated
- 2025/07/31
- Product number
- D3069
- Product name
- Diethyl Allylphosphonate
- Purity
- >95.0%(GC)
- Packaging
- 1g
- Price
- $36
- Updated
- 2025/07/31
- Product number
- D3069
- Product name
- Diethyl Allylphosphonate
- Purity
- >95.0%(GC)
- Packaging
- 5g
- Price
- $101
- Updated
- 2025/07/31
- Product number
- D493045
- Product name
- Diethyl allylphosphonate
- Packaging
- 500mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- 102088
- Product name
- Diethyl allylphosphonate
- Packaging
- 5g
- Price
- $75
- Updated
- 2021/12/16
Diethyl allylphosphonate Chemical Properties,Usage,Production
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Diethyl allylphosphonate manufacturers
- Product
- Diethyl allylphosphonate 1067-87-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 2T
- Release date
- 2023-12-21
- Product
- DIETHYL ALLYLPHOSPHONATE 1067-87-4
- Price
- US $0.10/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10
- Release date
- 2024-07-07
- Product
- DIETHYL ALLYLPHOSPHONATE 1067-87-4
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200kg
- Release date
- 2020-01-03