3066-75-9

Basic information

• Product Name: DIETHYL ALLYL PHOSPHATE 98
• Synonyms: DIETHYL ALLYL PHOSPHATE 98;Diethyl Allyl Phosphate 98%;diethyl prop-2-enyl phosphate;phosphoric acid allyl diethyl ester;Allyl Diethyl Phosphate
• CAS NO: 3066-75-9
• Molecular Formula: C₇H₁₅O₄P
• Molecular Weight: 194.17
• Product Categories: Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds
• Mol File: 3066-75-9.mol

Chemical Properties

• Boiling Point: 45-46 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.169mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• CAS DataBase Reference: DIETHYL ALLYL PHOSPHATE 98(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ALLYL PHOSPHATE 98(3066-75-9)
• EPA Substance Registry System: DIETHYL ALLYL PHOSPHATE 98(3066-75-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3066-75-9(Hazardous Substances Data)

Usage

Uses

Used in the Wood Industry:
DIETHYL ALLYL PHOSPHATE 98 is used as a flame-retardant agent for the modification of rubber wood with styrene. This application enhances the safety and durability of rubber wood products by reducing their flammability.
Used in the Plastics and Composites Industry:
DIETHYL ALLYL PHOSPHATE 98 is used as a flame retardant additive in the preparation of rubber wood/polymer composite. Its incorporation into these materials improves their fire resistance, making them suitable for a range of applications where flame retardancy is crucial.
Used in the Pharmaceutical Industry:
DIETHYL ALLYL PHOSPHATE 98 can be used for the stereoselective synthesis of cisor trans-3-vinyl-β-lactam compounds. These compounds have potential applications in the development of new drugs, particularly in the field of antibiotics.
Used in the Surface Fabrication Industry:
DIETHYL ALLYL PHOSPHATE 98 is also used for the fabrication of amphoteric surfaces on silicone substrates. This application allows for the creation of specialized surfaces with unique properties, such as improved biocompatibility or enhanced chemical reactivity.

InChI:InChI=1/C7H15O4P/c1-4-7-11-12(8,9-5-2)10-6-3/h4H,1,5-7H2,2-3H3

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 107-18-6 allyl alcohol 
• 598-02-7 Diethyl phosphate 
• 106-95-6 allyl bromide 
• 64-17-5 ethanol 
• 681035-21-2 (2-oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diethyl ester 
• 2622-05-1 allylmagnesium bromide 
• 35335-22-9 Oxiranylidene-2,2-bis(phosphonic acid) tetraethyl ester 
• 762-04-9 phosphonic acid diethyl ester 
• 122-52-1 triethyl phosphite 

Downstream Products

• 94-66-6 2-allylcyclohexan-1-one 
• 36040-02-5 2,6-diallyl-1-cyclohexanone 
• 67679-08-7 (S)-2-acetyl-2-(2-propenyl)cyclohexanone 
• 58648-14-9 (R)-2-acetyl-2-(2-propenyl)cyclohexanone 
• 109387-97-5 cis-1-(4-Methoxyphenyl)-3-vinyl-4-benzoyl-2-azetidinone 
• 124156-22-5 cis-1-(4-Methoxyphenyl)-3-vinyl-4-(methoxycarbonyl)-2-azetidinone 
• 762-62-9 4,4-dimethylpent-1-ene 
• 40637-56-7 dimethyl allylmalonate 
• 16212-05-8 (allylsulfonyl)benzene 
• 1623-14-9 ethyl phosphate 
• 1123-34-8 1-allyl-1-cyclohexanol 
• 80735-94-0 1-Phenyl-3-buten-1-ol 

Relevant articles and documents

New insights into the chemistry of gem-bis(phosphonates): Unexpected rearrangement of Michael-type acceptors

The use of tetraethyl ethylidenebis(phosphonate) as a Michael acceptor with different nucleophiles was investigated. It was found that in some cases this compound undergoes phosphate removal, depending on the nature of the nucleophile. The chemical behavior of its epoxy derivative tetraethyl oxiranylidenebis(phosphonate) as an electrophile was also studied. This compound underwent a very attractive and remarkable phosphonate-phosphate rearrangement resulting in the enol phosphate 8 regardless of the nucleophile employed. Different mechanistic studies were conducted in an attempt to explain the mechanisms involved. To the best of our knowledge, this reaction constitutes a remarkable novelty, being the first reported rearrangement reaction of an epoxy derivative of a gem-bis(phosphonate). In addition, evidence supporting the involvement of a radical or a polar mechanism, depending on the nature of the nucleophile, is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Aerobic Allylic Amination Catalyzed by a Pd(OAc)2/P(OPh)3System with Low Catalyst Loading

A Pd(OAc)2/P(OPh)3 combination catalyzed Tsuji-Trost-Type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphates were employed as electrophiles. Other typical electrophiles, such as allylic acetate and carbonate, were marginally reactive. A Pd(0) complex, Pd[P(OPh)3]3, formed in situ was suggested as an active species by mechanistic experiments.

Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes

A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields. The resulting dienes were further transformed by Horner-type Wittig reactions and a Diels-Alder cycloaddition.

Synthetic method of asymmetric phosphate compound

The invention relates to the field of lithium ion batteries, and discloses a synthetic method of an asymmetric phosphate compound. The method comprises the following steps: reacting phosphorus oxychloride represented by a formula (I), a compound represent

Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement

A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.

Catalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes

We have developed catalytic anti-Markovnikov hydroallylation of terminal and functionalized internal alkynes. In this article, we describe the development of the reaction, exploration of the substrate scope, and a study of the reaction mechanism. Synthesis of skipped dienes through the hydroallylation of terminal alkyl and aryl alkynes with simple allyl phosphates and 2-substituted allyl phosphates is described. The hydroallylation of functionalized internal alkynes leads to the formation of skipped dienes containing trisubstituted alkenes. We demonstrate that the hydroallylation of internal alkynes can be used in the regio- and diastereoselective synthesis of complex trisubstituted alkenes. A mechanism of the hydroallylation reaction is proposed, and experimental evidence is provided for the key steps of the catalytic cycle. Stoichiometric experiments demonstrate an unexpected role of lithium alkoxide in the carbon-carbon bond-forming step of the reaction. A study of the hydrocupration of internal alkynes provides new insight into the structure, stability, and reactivity of alkenyl copper intermediates, as well as insight into the source of the regioselectivity in reactions of internal alkynes.

Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles

The room temperature, 1,3-dipolar cycloaddition reactions of the nitrile oxide obtained from (6-piperidin-1-yl-9H-purin-9-yl)acetaldehyde oxime upon phenyliodine(III) bis(trifluoroacetate) treatment with excess unsaturated alcohols as solvent resulted in isoxazoline or isoxazole derivatives in almost quantitative yields. Analogous derivatives were prepared from the reactions of unsaturated phosphates. Preliminary biological tests indicated inhibition of lipid peroxidation for some of the examined compounds.

Metal catalyst-free substitution of allylic and propargylic phosphates with diarylmethyl anions

Substitution of secondary allylic phosphates with the anions derived from Ar2CH2 with BuLi or LDA proceeded regioselectively and stereoselectively without a metal catalyst, affording inversion products in good yield. Similarly, propargylic phosphates gave propargylic products selectively.