7316-37-2

Usage

Uses

Used in Flame Retardant Polymers:
Diethyl 2,3-epoxypropylphosphonate is used as a flame retardant for enhancing the fire resistance of polymers. Its high thermal stability and flame retardant properties contribute to the creation of safer materials in industries where fire safety is a concern.
Used in Plasticizers:
In the plastics industry, DEEP serves as a plasticizer, improving the flexibility and workability of plastic materials. Its reactive epoxy group allows for crosslinking and polymer modification, which can enhance the overall performance of the plastic products.
Used in Resins and Coatings:
Diethyl 2,3-epoxypropylphosphonate is utilized as an additive in the production of resins and coatings to impart flame retardancy. This is particularly important in applications where surfaces may be exposed to high temperatures or potential fire hazards, such as in construction, automotive, and aerospace industries.
It is crucial to handle DEEP with care due to its toxic nature and potential health risks if not properly managed. Proper handling and storage protocols are essential to ensure the safety of workers and the environment during its use in various industrial applications.

InChI:InChI=1/C7H15O4P/c1-3-10-12(8,11-4-2)6-7-5-9-7/h7H,3-6H2,1-2H3

Upstream product

• 78-40-0 triethyl phosphate 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 122-52-1 triethyl phosphite 
• 1067-87-4 Diethyl allylphosphonate 

Downstream Products

• 95448-38-7 diethyl 2-hydroxy-3-phenylpropanephosphonate 
• 65345-06-4 diethyl-3-bromo-2-hydroxypropyl phosphonate 
• 170167-92-7 (3-Cyclohexyl-2-hydroxy-propyl)-phosphonic acid diethyl ester 
• 175027-94-8 diethyl 3-dibenzylamino-2-hydroxypropylphosphonate 
• 175027-96-0 (2-Amino-3-dibenzylamino-propyl)-phosphonic acid diethyl ester 
• 175027-95-9 (2-Azido-3-dibenzylamino-propyl)-phosphonic acid diethyl ester 
• 175027-97-1 (2-tert-Butoxycarbonylamino-3-dibenzylamino-propyl)-phosphonic acid diethyl ester 
• 1234345-28-8 C₁₆H₂₄N₅O₆P 
• 1234345-30-2 C₁₇H₂₇N₄O₄P 
• 1234345-32-4 C₁₆H₂₅N₄O₄P 

Relevant academic research and scientific papers

Synthesis of polyols bearing phosphonate groups. Part II: Epoxides used as starting materials

Three epoxyphosphonates were prepared. These compounds have the following general formula: CH2(O)C(R)-Z-PO(OCH2CH3)2with (II): R=H, Z=CH2; (V): R=H, Z=CH2O(CH2)3S(CH2)3; (VI): R=CH3. (II) is obtained by epoxidation of diethyl allylphosphonate by hydrogen peroxide in the presence of benzonitrile with a yield superior to 60%. (V) is obtained by photoaddition of HS(CH2)3PO(OCH2CH3)2 to allyl glycidyl ether CH2(O)CH CH2-O-CH2CH=CH2 with a high yield. (VI) is obtained by addition of diethyl hydrogenophosphonate HPO(OCH2CH3)2 to 1-chloropropan-2-one CH3C(O) CH2Cl with a yield of 80%. These epoxides then lead to polyols bearing a phosphonate group by ring opening with diethanolamine (HOCH2CH2)2NH: (HOCH2CH2)2NCH2C(OH)(R)-Z-PO(OCH2CH3)2, with (VII): R=H, Z=CH2; (VIII): R=H, Z=CH2O(CH2)3S(CH2)3; (IX): R= CH3. This reaction appears to be an easy method without any need for solvent or catalyst, and could be of industrial interest.

EPOXY PHOSPHONATE ESTER AS A COUPLING AGENT FOR TRANSITION METAL AND METAL OXIDE SURFACES

A method for surface modification of a substrate comprising surface oxide and/or hydroxy groups, with a compound comprising an ester group and an epoxy ring, wherein the epoxy group remains intact after the reacting. A method for surface modification of a substrate comprising surface oxide and/or hydroxy groups, with a compound comprising an ester group and a functionalized epoxy ring, wherein the functionalized epoxy group remains intact after the reacting. A composite material comprising surface-modified metal oxide nanoparticles dispersed within a polymeric material, wherein the surface modification comprises a compound comprising an ester group and an epoxy ring is also described.

Synthesis and herbicidal activity of novel 1-(diethoxy-phosphoryl)-3-(4-one-1H-1,2,3-triazol-1-yl)-propan-2-yl carboxylic esters

A series of novel compounds, namely 1-(diethoxyphosphoryl)-3-(4-ones-1H-1,2,3-triazol-1-yl)propan-2-yl carboxylic esters, were designed on the basis of the diazafulvene intermediate of imidazole glycerol phosphate dehydratase (IGPD) and high-activity inhibitors of IGPD, and synthesized as inhibitors targeting IGPD in plants. Their structures were confirmed by 1 H- NMR, 13C-NMR, 31P-NMR and HR-MS. The herbicidal evaluation performed by a Petri dish culture method showed that most compounds possessed moderate to good herbicidal activities. Six compounds were chosen for further herbicidal evaluation on barnyard grass by pot experiments. 1-(Diethoxyphosphoryl)-3-(4-phenyl- 1H-1,2,3-triazol-1-yl)propan-2-yl 2-(naphthalen-1-yl)acetate (5-A3) and ethyl 1-(2-acetoxy-3-(diethoxyphosphoryl)propyl)-1H-1,2,3-triazole-4-carboxylate (5-B4) showed good herbicidal activities. Compared with the compounds with the best herbicidal activity ever reported, both compounds 5-A3 and 5-B4, which can inhibit the growth of barnyard grass at the concentration of 250g/hm2, efficiently gave rise to a nearly 4-fold increase of the herbicidal potency. However, their herbicidal activities were lower than that of acetochlor (62.5 g/hm2) in the pot experiments.

Fosmidomycin analogues with N-hydroxyimidazole and N-hydroxyimidazolone as a chelating unit

Fosmidomycin has been reported to have many biological activities as an antibacterial and antimalarial, along with being a herbicidal agent. Its unique mode of action involves the inhibition of a key step of the non mevalonate pathway by blockade of a crucial enzyme, the 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR), whose expression is present in bacteria, plasmodium parasites and higher plants, but not in mammals. Herein we report the development of fosmidomycin and of FR-900098 constrained analogues belonging to an unusual heterocyclic based complexing subunit involving N-hydroxyimidazoles and cyclic N-hydroxyureas.

REACTIVE FLAME RETARDANTS

The present invention relates to a phosphorus containing alcohol, obtainable or obtained by a process comprising the reaction of at least one alcohol with a phosphorus containing compound of the general formula (I) as defined herein, as well as the process for preparing a phosphorus containing alcohol, comprising the reaction of at least one alcohol with a phosphorus containing compound of the general formula (I). Furthermore, the present invention relates to the use of a phosphorus containing alcohol as disclosed herein as a flame retardant, to a process for the preparation of a polyurethane and the polyurethane as such.

Synthesis of a series of new racemic [2,3-bis(acyloxy)propyl] phosphonocholines

An efficient synthesis of [2,3-bis(acyloxy)propyl]phosphonocholines is described. The reaction pathway for the synthesis involves the Michaelis-Arbuzov reaction of allyl bromide with triethyl phosphite and epoxidation of the resulting diethyl (prop-2-en-1-yl)phosphonate (1) with m- CPBA to afford the phosphonated diol (3). The acylation of diol (3) with carboxylic acids gave a series of diacyloxypropylphosphonates (4). The introduction of choline to a pyridinium salt of [2,3-bis(acyloxy)propyl]phosphonic acid (5) was the most intensively studied reaction. The total yield of a six-step sequence synthesis of a series of phosphonolipids was in the range of 30-40%. ARKAT-USA, Inc.

Polyethylene glycol-promoted dialkyl, aryl/heteroaryl phosphonates

A new, straightforward polyethylene glycol-promoted method for Michaelis-Arbuzov rearrangement has been described.

Synthesis of β-hydroxyphosphonate and 1,2-dihydroxy acyclic nucleoside analogs via 1,3-dipolar cycloaddition strategy

A convenient synthetic approach toward nucleoside analogs where β-hydroxyphosphonate- or 1,2-dihydroxy units are connected to the nucleic acid base through a triazole spacer is discussed.

Double nucleophilic 1,2-addition of silylated dialkyl phosphites to 4-phosphono-1-aza-1,3-dienes: Synthesis of γ-phosphono-α- aminobisphosphonates

(Chemical Equation Presented) γ-Phosphono-α- aminobisphosphonates were synthesized from a new class of 4-phosphono-1-aza-1,3- dienes by the addition of dialkyl trimethylsilyl phosphites to these azadienes in the presence of acid. Depending on the steric demand of the group on nitrogen, double 1,2-addition or tandem 1,4-1,2-addition occurred.

Synthesis of Substrate Analogues and Inhibitors for the Phosphoglycerate Mutase Enzyme

Several substrate analogues of the title enzyme were synthesized as well as with possible irreversible inhibitors, analogues of phosphoglycolate, the cofactor for this enzyme.The main routes involved an Arbuzov type reaction on functionalized halides, a reaction significantly improved by a sonication procedure and reaction of the diethylphosphite anion on tosylates.Phosphorylated epoxides were obtained by quantitative oxidation of conjugate double bonds using DMDO.Preliminary assays indicated a promising activity in some of these compounds.Keywords: phosphonates; inhibitors; phosphoglycerate Mutase; Arbuzov; DMDO