2404-58-2

Basic information

• Product Name: dibutyl ethylphosphonate
• Synonyms: Dibutyl ethylphosphonate; phosphonic acid, P-ethyl-, dibutyl ester
• CAS NO: 2404-58-2
• Molecular Formula: C₁₀H₂₃O₃P
• Molecular Weight: 222.2616
• Mol File: 2404-58-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 282.6°C at 760 mmHg
• Flash Point: 138.6°C
• Density: 0.964g/cm³
• Vapor Pressure: 0.00569mmHg at 25°C
• Refractive Index: 1.423
• CAS DataBase Reference: dibutyl ethylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: dibutyl ethylphosphonate(2404-58-2)
• EPA Substance Registry System: dibutyl ethylphosphonate(2404-58-2)

Safety Data

• Hazardous Substances Data: 2404-58-2(Hazardous Substances Data)

Upstream product

• 3058-20-6 dibutyl butylphosphonite 
• 106-89-8 epichlorohydrin 
• 6779-09-5 ethylphosphonic acid 
• 71-36-3 butan-1-ol 
• 1929-44-8 monobutyl ethylphosphonate 
• 1066-50-8 Ethylphosphonic dichloride 
• 74-96-4 ethyl bromide 
• 1809-19-4 dibutyl hydrogen phosphite 
• 75-03-6 ethyl iodide 
• 4124-92-9 dibutyl chlorophosphite 
• 925-90-6 ethylmagnesium bromide 
• 102-85-2 tri-n-butyl phosphite 
• 126-73-8 phosphoric acid tributyl ester 

Downstream Products

• 1066-50-8 Ethylphosphonic dichloride 
• 6779-09-5 ethylphosphonic acid 

Relevant articles and documents

Microwave-assisted ionic liquid-catalyzed selective monoesterification of alkylphosphonic acids—an experimental and a theoretical study

It is well-known that the P-acids including phosphonic acids resist undergoing direct es-terification. However, it was found that a series of alkylphoshonic acids could be involved in mo-noesterification with C2–C4 alcohols under microwave (MW) irradiation in the presence of [bmim][BF4] as an additive. The selectivity amounted to 80–98%, while the isolated yields fell in the range of 61–79%. The method developed is a green method for P-acid esterification. DFT calculations at the M062X/6–311+G (d,p) level of theory (performed considering the solvent effect of the corresponding alcohol) explored the three-step mechanism, and justified a higher enthalpy of activation (160.6–194.1 kJ·mol–1) that may be overcome only by MW irradiation. The major role of the [bmim][BF4] additive is to increase the absorption of MW energy. The specific chemical role of the [BF4] anion of the ionic liquid in an alternative mechanism was also raised by the computations.

Method for the production of alkylphosphonic acids, esters, and salts by oxidizing alkylphosphonous acids, and use thereof

The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand.

An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride

Silica chloride is used as an effective heterogeneous catalyst for the rapid esterification of alkyl/aryl phosphonic/phosphoric acids to their corresponding alkyl/aryl phosphonates/phosphates under mild conditions with quantitative yields.