78-46-6

Usage

Uses

Used in Organic Synthesis:
Dibutyl butanephosphonate is used as a reagent in organic synthesis for various chemical reactions. Its phosphonic acid ester group allows it to participate in a range of reactions, making it a valuable component in the synthesis of different organic compounds.
Used in Uranium Extraction:
In the nuclear industry, dibutyl butanephosphonate is utilized as an extractant for uranium extraction. Its ability to form complexes with uranium ions makes it an effective agent in the separation and purification processes of uranium from other elements.
Used in the Plasticizing Industry:
Dibutyl butanephosphonate is also employed in the plasticizing industry as a plasticizer. It is added to polymers to increase their flexibility, workability, and elongation at break. This improves the overall performance and durability of the final plastic products, making them more suitable for various applications.

Safety Profile

Poison by intraperitoneal and intravenous routes. Combustible when exposed to heat or flame. It can react vigorously with oxidizing materials. To fight fire, use foam, CO2, or dry chemical. When heated to decomposition it emits toxic fumes of POx.

Purification Methods

Purify by three recrystallisations of its compound with uranyl nitrate, from hexane. For method, see tributyl phosphate.

InChI:InChI=1/C12H27O3P/c1-4-7-10-14-16(13,12-9-6-3)15-11-8-5-2/h4-12H2,1-3H3

Upstream product

• 542-69-8 1-iodo-butane 
• 102-85-2 tri-n-butyl phosphite 
• 693-03-8 n-butyl magnesium bromide 
• 819-43-2 dibutyl chlorophosphate 
• 109-65-9 1-bromo-butane 
• 1809-19-4 dibutyl hydrogen phosphite 
• 2302-80-9 butylphosphonic dichloride 
• 71-36-3 butan-1-ol 
• 109-72-8 n-butyllithium 
• 126-73-8 phosphoric acid tributyl ester 
• 123-86-4 acetic acid butyl ester 
• 2567-59-1 N,N-di-n-butyl-2-chloroacetamide 
• 109-47-7 dibutyl hydrogen phosphite 
• 998-40-3 tributylphosphine 

Downstream Products

• 2302-80-9 butylphosphonic dichloride 
• 3321-64-0 butylphosphonic acid 

Relevant academic research and scientific papers

Lipid-mimicking phosphorus-based glycosidase inactivators as pharmacological chaperones for the treatment of Gaucher's disease

Gaucher's disease, the most prevalent lysosomal storage disorder, is caused by missense mutation of the GBA gene, ultimately resulting in deficient GCase activity, hence the excessive build-up of cellular glucosylceramide. Among different therapeutic strategies, pharmacological chaperoning of mutant GCase represents an attractive approach that relies on small organic molecules acting as protein stabilizers. Herein, we expand upon a new class of transient GCase inactivators based on a reactive 2-deoxy-2-fluoro-β-d-glucoside tethered to an array of lipid-mimicking phosphorus-based aglycones, which not only improve the selectivity and inactivation efficiency, but also the stability of these compounds in aqueous media. This hypothesis was further validated with kinetic and cellular studies confirming restoration of catalytic activity in Gaucher cells after treatment with these pharmacological chaperones.

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 PRODUCING ORGANOPHOSPHORUS COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an organophosphorus compound which has excellent energy efficiency without containing a halogenated alkyl or a by-product derived from a halogenated alkyl. SOLUTION: There is provided a method for producing an organophosphorus compound by reacting a trivalent organophosphorus compound represented by the following general formula (1) in the presence of a super strong acid and/or at least one acid catalyst containing a solid superstrong acid catalyst to generate a pentavalent organophosphorus compound represented by the following general formula. (where Z1 represents OR2 or R2; Z2 represents OR3 or R3; R1, R2 and R3 represent an alkyl group, an alkenyl group or the like; when R2 and R3 are an alkyl group or the like, R2 and R3 may be bonded to each other to form a cyclic structure; and R1 may be a hydrogen atom.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.

Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel

The use of simple and inexpensive NiCl2?6 H2O as a catalyst precursor for C?P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. Control experiments showed the in situ formation of (RO)2P(O)H as the species that undergo the addition into the C≡C bond at the alkynes to yield the product of P?H addition. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand. This method is useful for the preparation of organophosphonates for both phenylacetylene as a terminal alkyne model and internal alkynes in yields that range from good to modest.

A Library of Well-Defined and Water-Soluble Poly(alkyl phosphonate)s with Adjustable Hydrolysis

Poly(alkyl ethylene phosphonate)s with different alkyl side chains exhibit significant differences in their degradation behavior. Three novel 2-alkyl-2-oxo-1,3,2-dioxaphospholanes, cyclic monomers for the ring-opening polymerization (ROP) toward poly(alkyl alkylene phosphonate)s, were synthesized by robust two- or three-step protocols in reasonable yields and high purity. The polymerization was promoted by the organocatalysts 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and proceeded with high control over molecular weight and narrow molecular weight distributions (A 1.2) up to full conversion. These polymers with methyl, ethyl, and isopropyl side chains are perfectly soluble in water (up to 25 mg mL-1) without a temperature-dependent phase separation. They showed no toxicity against HeLa cells after 24 h of incubation at any tested concentration. Polymers with butyl side chains exhibit decreased solubility and concentration-dependent cloud point temperatures and show toxicity against HeLa cells at concentrations above 25 mL-1. The polymers showed no acetylcholinesterase inhibition. All polymers exhibited significantly different degradation times under both neutral as well as basic conditions (variation of the alkyl side chain allowed stabilities from 8 h up to 6 days).

Synthesis, purification, and characterization of phosphine oxides and their hydrogen peroxide adducts

Reactions of the tertiary phosphines R3P (R = Me, Bu, Oct, Cy, Ph) with 35% aqueous H2O2 gives the corresponding oxides as the H2O2 adducts R3PO·(H 2O2)x (x = 0.5-1.0). Air oxidation leads to a mixture of products due to the insertion of oxygen into one or more P-C bonds. 31P NMR spectroscopy in solution and in the solid state, as well as IR spectroscopy reveal distinct features of the phosphine oxides as compared to their H2O2 adducts. The single crystal X-ray analyses of Bu3PO and [Cy3PO·(H2O2)] 2 show a PO stacking motif for the phosphine oxide and a cyclic structure, in which the six oxygen atoms exhibit a chair conformation for the dimeric H2O2 adduct. Different methods for the decomposition of the bound H2O2 and the removal of the ensuing strongly adsorbed H2O are evaluated. Treating R 3PO·(H2O2)x with molecular sieves destroys the bound H2O2 safely under mild conditions (room temperature, toluene) within one hour and quantitatively removes the adsorbed H2O from the hygroscopic phosphine oxides within four hours. At 60°C the entire decomposition/drying process is complete within one hour.

Electrocatalytic eco-efficient functionalization of white phosphorus

The novel eco-efficient methods to transform white phosphorus into the esters of phosphoric, phosphorous and phosphonic acids, tertiary phosphines and other organophosphorus compounds under conditions of electrochemical catalysis were elaborated. The mechanism of these processes was investigated using the method of cyclic voltammetry and preparative electrolysis.

Optimization of 2-chloroethylphosphonic acid synthesis by acid hydrolysis of dialkyl-2-chloroethylphosphonate compounds. Influence of the nature of alkyl phosphonate functions

2-Chloroethylphosphonic acid (ethephon) 1 is very much used in agriculture as a plant regulator.It is an especially good stimulant used to increase the latex production of Hevea brasiliensis.Ethephon is generally obtained by HCl hydrolysis of bis(2-chloroethyl)-2-chloroethylphosphonate, previously prepared by Arbuzov rearrangement of tri(2-chloroethyl)phosphite.However, because of the low reactivity of 2-chloroethylphosphonate functions towards acid hydrolysis, this synthetic way is not convenient to prepare pure 2-chloroethylphosphonic acid with high yields.The present purpose was to study the hydrolysis of various dialkyl-2-chloroethylphosphonates in view to define an efficient synthetic protocol, leading to very pure crystallized ethephon with high yields. - Keywords: 2-chloroethylphosphonic acid; ethephon; dialkyl-2-chloroethylphosphonate; Arbuzov reaction; trialkyl phosphite; acid hydrolysis

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.