7316-37-2

Basic information

• Product Name: diethyl 2,3-epoxypropylphosphonate
• Synonyms: diethyl 2,3-epoxypropylphosphonate;(Oxiran-2-ylmethyl)phosphonic acid diethyl ester;Glycidylphosphonic acid diethyl ester;Oxiranylmethylphosphonic acid diethyl ester
• CAS NO: 7316-37-2
• Molecular Formula: C₇H₁₅O₄P
• Molecular Weight: 194.165361
• EINECS: 230-778-9
• Mol File: 7316-37-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 45.5°C (estimate)
• Flash Point: 130.1°C
• Appearance: /
• Density: 1.154g/cm³
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: 1.44
• CAS DataBase Reference: diethyl 2,3-epoxypropylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 2,3-epoxypropylphosphonate(7316-37-2)
• EPA Substance Registry System: diethyl 2,3-epoxypropylphosphonate(7316-37-2)

Safety Data

• Hazardous Substances Data: 7316-37-2(Hazardous Substances Data)

Usage

General Description

Diethyl 2,3-epoxypropylphosphonate, also known as DEEP, is a chemical compound commonly used as a flame retardant and plasticizer in various industrial applications. It is a phosphorus-containing compound with a reactive epoxy group, making it suitable for crosslinking and polymer modification. DEEP is known for its high thermal stability and flame retardant properties, making it a valuable additive in the production of flame-retardant polymers, resins, and coatings. However, it is important to handle DEEP with care, as it is considered toxic and poses health risks if not properly handled and stored. Overall, diethyl 2,3-epoxypropylphosphonate plays a significant role in enhancing the safety and durability of various materials in the industrial sector.

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

Upstream product

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

Downstream Products

• 146792-99-6 (E)-2-(3'-diethoxyphosphonyl)propylidenecyclohexanone 

Relevant articles and documents

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.

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.

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.