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Diethyl allylphosphonate

CAS No.1067-87-4
Chemical Name:Diethyl allylphosphonate
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
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)
UNSPSC Code 12352108
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :26-36
WGK Germany :3
HS Code :29319090

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

Diethyl allylphosphonate Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 565415
Product name : Diethyl allylphosphonate
Purity: 98%
Packaging: 5G
Price: ₹7978.03
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: D3069
Product name : Diethyl Allylphosphonate
Purity: min. 95.0 %
Packaging: 1G
Price: ₹3000
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D3069
Product name : Diethyl Allylphosphonate
Purity: min. 95.0 %
Packaging: 5G
Price: ₹7400
Updated: 2022/05/26
Buy: Buy

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.