2302-80-9

Usage

Uses

Used in Chemical Synthesis:
BUTYLPHOSPHONIC DICHLORIDE is used as a reagent for the synthesis of macrocyclic phosphonates, which are compounds with potential antimicrobial properties.
Used in Antimicrobial Research:
In the field of antimicrobial research, BUTYLPHOSPHONIC DICHLORIDE is used as a reagent to evaluate the efficacy of newly synthesized macrocyclic phosphonates in suppressing the growth of bacteria and fungi. This application aids in the development of novel antimicrobial agents to combat resistant strains and improve public health.

InChI:InChI=1/C4H9Cl2OP/c1-2-3-4-8(5,6)7/h2-4H2,1H3

Upstream product

• 78-46-6 dibutyl butylphosphonate 
• 106-97-8 n-butane 
• 6460-27-1 butyldichlorophosphine 
• 2404-75-3 butyldiethylphosphonate 
• 24475-23-8 O,O-dimethyl butylphosphonate 
• 7719-12-2 phosphorus trichloride 
• 75-44-5 phosgene 

Downstream Products

• 93902-23-9 N,N'-Dibenzyl-n-butan-phosphonsaeure-⁽¹⁾-diamid 
• 101632-96-6 1,3-Dibenzyl-2,4-dibutyl-[1,3,2,4]diazadiphosphetidine 2,4-dioxide 
• 78-46-6 dibutyl butylphosphonate 
• 6588-22-3 Butyl-thiophosphonsaeure-dichlorid 
• 28364-13-8 Cyclohexyl-butylphosphonochloridat 
• 556031-70-0 3-(benzyloxy-butyl-phosphinoyloxy)-octanoic acid tert-butyl ester 
• 106409-25-0 Dimeres N-<4-Chlor-phenyl>-butan-phosphonsaeure-(1)-imid 
• 1352001-82-1 13-phenyl-2,4,8,10-tetramethyl-6-butyl-13,14-dihydro-12H-6λ5-dibenzo[d,i][1,3,7,2]dioxazaphosphecin-6-one 
• 1352001-84-3 13-(2-methoxyphenyl)-2,4,8,10-tetramethyl-6-butyl-13,14-dihydro-12H-6λ5-dibenzo[d,i][1,3,7,2]dioxazaphosphecin-6-one 
• 1352001-83-2 13-(4-methoxyphenyl)-2,4,8,10-tetramethyl-6-butyl-13,14-dihydro-12H-6λ5-dibenzo[d,i][1,3,7,2]dioxazaphosphecin-6-one 
• 1352001-87-6 13-(4-methylphenyl)-2,4,8,10-tetramethyl-6-butyl-13,14-dihydro-12H-6λ5-dibenzo[d,i][1,3,7,2]dioxazaphosphecin-6-one 

Relevant academic research and scientific papers

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).

Inhibition of human gastric and pancreatic lipases by chiral alkylphosphonates. A kinetic study with 1,2-didecanoyl-sn-glycerol monolayer

Enantiomerically pure alkylphosphonate compounds RR'P(O)PNP (R=C(n)H(2n+1), R'=OY with Y=C(n')H(2n'+1) with n=n' or n≠n'; PNP=p-nitrophenoxy) noted (RY), mimicking the transition state occurring during the carboxyester hydrolysis were synthesized and investigated as potential inhibitors of human gastric lipase (HGL) and human pancreatic lipase (HPL). The inhibitory properties of each enantiomer have been tested with the monomolecular films technique in addition to an enyzme linked immunosorbent assay (ELISA) in order to estimate simultaneously the residual enzymatic activity as well as the interfacial lipase binding. With both lipases, no obvious correlation between the inhibitor molar fraction (α50) leading to half inhibition, and the chain length, R or Y was observed. (R11Y16)s were the best inhibitor of HPL and (R10Y11)s were the best inhibitors of HGL. We observed a highly enantioselective discrimination, both with the pure enantiomeric alkylphosphonate inhibitors as well as a scalemic mixture. We also showed, for the first time, that this enantioselective recognition can occur either during the catalytic step or during the initial interfacial adsorption step of the lipases. These experimental results were analyzed with two kinetic models of covalent as well as pseudo-competitive inhibition of lipolytic enzymes by two enantiomeric inhibitors. Copyright (C) 1999 Elsevier Science Ireland Ltd.

Easy preparation of alkylphosphonyl dichlorides

Phosphonic acid esters bearing an alkyl, halogen or carboxylate substituent on the α-carbon are readily converted into the parent phosphonic dichlorides when treated with a mixture of 2.5 eq of phosphorus pentachloride and 1.3 eq of phosphorus oxychloride.Keywords - phosphonates / chlorination / phosphorus pentachloride / phosphorus oxychloride / phosphonyl dichloride

Process for the preparation of phosphonic acid dihalides

Process for preparing phosphonic acid dihalides of the formula EQU1 wherein R is alkyl of 1 to 18 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, alkenyl of 2 to 18 carbon atoms, phenyl, phenalkyl or alkyl-phenyl of 7 to 8 carbon atoms, phenyl, phenalkyl or alkyl-phenyl of 7 to 8 carbon atoms, all radicals R optionally being substituted by chlorine, bromine, cyano or lower acyloxy, and wherein X is halogen such as 2-chloroethane phosphonic acid dichloride, by reacting phosphonic or thio-phosphonic acids of the formula EQU2 wherein Y is oxygen or sulfur, their salts or functional derivatives, with acid halides of the formula wherein X is chlorine or bromine and n is 1 or 2, in the presence of 0.2 - 5% or in the presence of 0.01 to 0.2% by weight of 1. compounds containing at least one tri- to pentavalent nitrogen or phosphorus atom, which in the case of nitrogen is bound with 1 to 4, in the case of phosphorus with at least 3 valences to organic radicals having up to 20 carbon atoms, two of these valences optionally forming a double bond, or 2. mono-di- or tribasic organic or inorganic fully amidated acids or tri- or pentavalent phosphorus, the N atom of which optionally being substituted by aliphatic radicals having up to 20 carbon atoms, and the organic radicals of which contain up to 20 carbon atoms, If required, in the presence of an inert solvent.