50655-63-5

Usage

Uses

Used in Plastics and Rubber Industry:
Diethyl isobutylphosphonate is used as a flame retardant and plasticizer for improving the fire resistance and flexibility of materials.
Used in Textile Industry:
Diethyl isobutylphosphonate is used as a flame retardant and plasticizer in the production of textiles to enhance their durability and resistance to fire.
Used in Pharmaceutical and Agrochemical Synthesis:
Diethyl isobutylphosphonate is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
However, it is important to handle this chemical with care as it can be toxic if ingested or inhaled, and it may pose environmental hazards if not properly managed.

Upstream product

• 64-17-5 ethanol 
• 5021-98-7 isobutyl-phosphonic acid-dichloride 
• 78-40-0 triethyl phosphate 
• 920-36-5 (2-methylpropyl)lithium 
• 18689-32-2 diethyl (E)-1-propenylphosphonate 
• 144-79-6 chloromethyldiphenylsilane 
• 917-54-4 methyllithium 
• 110-05-4 di-tert-butyl peroxide 
• 762-04-9 Diethyl phosphonate 
• 115-11-7 isobutene 
• 1262726-76-0 C₈H₁₉N₂O₃P 
• 20208-71-3 4-methyl-N'-(2-methylpropylidene)benzenesulfonohydrazide 
• 762-04-9 phosphonic acid diethyl ester 
• 136527-36-1 Isobutyl-phosphonic acid monoethyl ester 

Downstream Products

• 13538-11-9 isobutyl-phosphonic acid ethyl ester-(4-nitro-phenyl ester) 

Relevant academic research and scientific papers

Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates

Herein is described the development of an intensified continuous flow process for the preparation of a library of alkyl phosphonates through a Michaelis-Arbuzov rearrangement. A careful process optimization and thorough analysis of the competitive reactions led to a very attractive protocol with unprecedented productivities (up to 4.97 kg of material per day) and a low environmental footprint with the absence of solvent, additives, catalysts, and waste. In-line low-field 31P NMR monitoring was conveniently implemented for rapid optimization and process monitoring. Two key alkyl phosphonate intermediates were also assessed for the unprecedented diazene dicarboxylate-mediated electrophilic amination under continuous flow conditions toward the α-aminophosphonic acid derivatives of Pphenylalanine and Palanine, bioisosters of the natural amino acids phenylalanine and alanine, respectively.

Fragmentation-Related Phosphonylation of Nucleophiles Utilizing P-Alkyl 2,3-oxaphosphabicyclo[2.2.2]octene 3-oxide Precursors

New P-alkyl 2,3-oxaphosphabicyclo-[2.2.2]octene 3-oxides were synthesized by the Bayer-Villiger oxidation of the corresponding 7-phosphanorbornene 7-oxides and were used as precursors for reactive alkylmetaphosphonates useful in the phosphonylation of alcohols. This is the first case that the reactivity of the two regioisomers formed by O-insertion was differentiated and that the fragmentation-related phosphonylation leading to phosphonic acid-esters was achieved under microwave-assisted conditions.

Reductive coupling reactions: A new strategy for C(sp3)-P bond formation

The C(sp3)-P bond forming reaction utilizing N-tosylhydrazones as readily available alkylating reagents was developed, which provides a new opportunity for preparing phosphine oxide derivatives with moderate to good yields. This reductive coupling reaction is proposed to proceed through an insertion of copper carbene into P-H bond of H-phosphorus oxides. The salient features of the reaction are operational simplicity and functional-group tolerance.

Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.

Room-temperature alternative to the arbuzov reaction: The reductive deoxygenation of Acyl phosphonates

The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.

Acceleration of nucleophilic addition to vinylphosphonates and vinyl phosphine oxides by chlorotrimethylsilane

Chlorotrimethylsilane significantly accelerates the conjugate addition of alkyl cuprates to vinylphosphonates.

Phosphate-phosphonate conversion: a versatile route to linear or branched alkylphosphonates

Addition of a symmetrically substituted trialkyl phosphate (R1O)3P(O) to a THF solution of an alkyllithium R2-CH2Li (2 equiv) at -78 deg C, followed by warming to room temperature, results in the quantitative formation of α-lithioalkylphosphonate.Treatment of the anion formed with aqueous HCl or an alkyl iodide yields the corresponding alkylphosphonate or α-substituted alkylphosphonate in good to excellent yields.Key Words: trialkyl phosphonates; alkyllithiums; α-lithioalkylphosphonates; alkylphosphonates.

CONVERSION DIRECTE PAR LES ALKYLLTHIENS DES PHOSPHATES EN PHOSPHONATES α-LITHIES

Trialkylphosphates (RO)3P(O) can be converted into α-lithioalkanephosphonates by treatment with alkyllithiums (R1CH2Li) in two fold excess.

Organophosphonic acids or esters containing an epoxy group

A method for protecting the surface of a metal surface which comprises applying to said surface an organophosphorus compound of the formula STR1 wherein A IS 0 OR 1 R is a branched or unbranched chained bivalent alkylene radical of 1 to 12 carbon atoms which is substituted or unsubstituted and can contain in the chain structure --O--, --S--, STR2 R' is a branched or unbranched alkyl radical of 1 to 12 carbon atoms which can be halogen substituted and can contain in the chain structure STR3 X is an epoxy ring, halogen, alkylene, carboxylic acid ester residue, amino, isocyanato, isothiocyanato, urea, thiourea, urethano, alkyl substituted thio radical or the radical or a heterocyclic ring containing O, S or N in the ring structure; a new organophosphorus compounds having the formula set forth above and more particularly defined by specific chemical structures.