Diethyl allylphosphonate

Product Name: Diethyl allylphosphonate
CAS No.: 1067-87-4
Chemical Name: Diethyl allylphosphonate
Synonyms: AURORA KA-1466;DIETHYL ALLYLPHOSPHONATE;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

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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)

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Safety

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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 565415
Product name: Diethyl allylphosphonate
Purity: 98%
Packaging: 5g
Price: $114
Updated: 2024/03/01

TCI Chemical

Product number: D3069
Product name: Diethyl Allylphosphonate
Purity: >95.0%(GC)
Packaging: 1g
Price: $30
Updated: 2024/03/01

TCI Chemical

Product number: D3069
Product name: Diethyl Allylphosphonate
Purity: >95.0%(GC)
Packaging: 5g
Price: $84
Updated: 2024/03/01

TRC

Product number: D493045
Product name: Diethyl allylphosphonate
Packaging: 500mg
Price: $90
Updated: 2021/12/16

Frontier Specialty Chemicals

Product number: JK471489
Product name: Diethyl allylphosphonate
Purity: 97%
Packaging: 5g
Price: $108
Updated: 2021/12/16

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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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Diethyl allylphosphonate Suppliers

Americas 1 Austria 1 Belgium 1 China 101 Europe 1 France 2 Germany 2 India 3 Japan 2 Switzerland 1 United Kingdom 5 United States 10 Global 130

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View Lastest Price from Diethyl allylphosphonate manufacturers

XINXIANG RUNYU MATERIAL CO., LTD.

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

Shaanxi Dideu Medichem Co. Ltd

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

Career Henan Chemical Co

Product: DIETHYL ALLYLPHOSPHONATE 1067-87-4
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 200kg
Release date: 2020-01-03

1067-87-4, Diethyl allylphosphonateRelated Search:

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

DIETHYL(PROP-1(E)-ENYL)PHOSPHONATE

DIETHYL(PROP-2-(E)-ENYL)PHOSPHONATE

DIETHYL-(ALLYLPHOSPHONAT)

DIETHYL ALLYLPHOSPHONATE

DIETHYL-(2-PROPENYL)-PHOSPHONAT

DIETHYL(2-PROPENYL)PHOSPHONATE

DIETHYL (1-PROPENYL)PHOSPHONATE

AURORA KA-1466

ALLYLPHOSPHONIC ACID DIETHYL ESTER

Diethylallylphosphonate, 97 %

Diethyl allylphosphonate, 95+%

(2-Propenyl)phosphonic acid diethyl ester

2-Propenylphosphonic acid diethyl

Allylphosphonic acid diethyl

DiethylAllylphosphonate&gt

Phosphonic acid, P-2-propen-1-yl-, diethyl ester

3-diethoxyphosphorylprop-1-ene

Diethyl?P-2-propen-1-ylphosphonate

DIETHYL ALLYLPHOSPHONATE

1067-87-4

C2H5O2POCH2CHCH2

CH2CHCH2POOC2H52

C7H15O3P

C-C Bond Formation

Synthetic Reagents

Horner-Wadsworth-Emmons Reagents

Olefination

C-C Bond Formation

Horner-Wadsworth-Emmons Reagents

Olefination