1498-54-0

Usage

Uses

Used in Molecular Biology and Genetic Research:
DICHLORO N,N-DIETHYLPHOSPHORAMIDITE is used as a phosphitylating reagent for the activation of hydroxyl groups on phosphoramidite linkers in the solid phase synthesis of oligonucleotides. This activation is essential for the stepwise addition of nucleotide units, facilitating the creation of custom-designed oligonucleotides for various applications in molecular biology and genetic research.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, DICHLORO N,N-DIETHYLPHOSPHORAMIDITE is used as a key component in the synthesis of therapeutic oligonucleotides, which have potential applications in treating genetic disorders and diseases by modulating gene expression or inhibiting specific proteins.
Used in Diagnostics:
DICHLORO N,N-DIETHYLPHOSPHORAMIDITE is utilized in the development of diagnostic tools, such as DNA or RNA probes, which are essential for detecting and identifying specific genetic sequences in various testing methods, including PCR, sequencing, and microarrays.
Used in Research and Development:
In research and development, DICHLORO N,N-DIETHYLPHOSPHORAMIDITE is employed as a versatile reagent for the synthesis of modified oligonucleotides with unique properties, such as increased stability, enhanced binding affinity, or specific chemical modifications for various experimental purposes.

InChI:InChI=1/C4H10Cl2NOP/c1-3-7(4-2)9(5,6)8/h3-4H2,1-2H3

Upstream product

• 109-89-7 diethylamine 
• 100521-59-3 B-Tris-dimethylamino-N-triethyl-borazol 
• 1069-08-5 diethylphosphoramidous dichloride 
• 5775-33-7 N-chlorodiethylamine 
• 660-68-4 diethyl amine hydrochloride 

Downstream Products

• 63815-60-1 cyano-phosphonic acid ethyl ester-diethylamide 
• 24590-39-4 Butyldiaethylamidochlorphosphat 
• 6214-04-6 diphenyl diethylphosphoramidate 
• 25316-38-5 N,N-diethylphosphoric acid triamide 
• 359-94-4 diethyl-amidophosphoryl fluoride 
• 56372-47-5 N,N-diethyl P,P-diphenylphosphinamide 
• 1794-24-7 tetraethyldiamidochlorophosphate 
• 20434-05-3 bis(4-methoxyphenyl)phosphinic acid 
• 114617-74-2 di-(2-methoxyphenyl)phosphinic acid 
• 1084-11-3 bis(4-methylphenyl)phosphinic acid 
• 93973-59-2 N,N-diethyl-di(2-thienyl)phosphinic amide 
• 75840-56-1 2-(diethylamino)-5-methyl-3-phenyl-1,3,2-oxazaphospholidine 2-oxide 
• 129835-85-4 N,N-diethyl-P-(3,5-dimethyl-4-hydroxyphenyl)-phosphonamidic chloride 
• 53859-37-3 2-(Diethylamino)-2H-1,3,2-oxazaphosphorinan-2-oxid 

Relevant academic research and scientific papers

Synthesis of N, N-dialkyl phosphoramidic dichloride from dialkyl amine and phosphoryl chloride using basic anion exchange polymer resins/beads

An efficient and operationally simple method is developed for the syndesis of N, N-dialkyl phosphoramidic dichloride from dialkyl amine and phosphoryl chloride using basic anion exchange polymer resins/beads. In me reaction, polymer resin acts as a scavenger for HCl produced as by-product and desired product is distilled under vacuum. Reaction afforded N, N-dialkyl phosphoramidic dichloride in 3-4 hours with excellent yields from corresponding dialkylamine and phosphoryl chloride.

A new mechanism for nucleophilic substitution at a thiophosphoryl centre revealed by the reaction of diisopropylamine with PSCl3

The reaction of PSCl3 with Pri2NH at 60 °C affords the disubstitution product (Pri2N) 2P(S)Cl without first forming the monosubstitution product Pr i2NP(S)Cl2/su

Kinetic resolution of hydroperoxides with enantiopure phosphines: Preparation of enantioenriched tertiary hydroperoxides

An efficient reductive kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported. Readily accessible tertiary hydroperoxides are resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37. The resulting bis(phosphine oxide) can be recycled in high yields. The isolated mono(phosphine oxide) intermediate resolved hydroperoxides with the same selectivity as the parent bisphosphine. Copyright

Hydrolysis of cyclic phosphoramides. Evidence for syn lone pair catalysis

Hydrolysis between 1.5 31PNMR spectroscopy. The observed rates fit the equation: kobs = kH2O[H+]/([H+] + Ka) + k′su

Studies on chiral thiophosphoric acids and their derivatives 16. - The asymmetric cyclization of L-(+)-prolinol with (thio)phosphoro(-no)dichloridates

The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.

Synthesis, Activation, and Cytotoxicity of Aldophosphamide Analogues

A series of perhydrooxazine analogues of aldophosphamide has been prepared, and their 31P NMR kinetics and in vitro cytotoxicity have been evaluated.These compounds were developed on the basis of the idea that ring opening and tautomerization to an enamine intermediate might provide a mechanistic alternative to the β-elimination reaction for release of phosphoramide mustard.The 4,4,6-trimethyltetrahydro-1,3-oxazine moiety was selected on the basis of its rapid rate of iminium ion generation and relatively slow rate of hydrolysis.These analogues underwent phosphorodiamidate release by three distinct mechanisms: hydrolysis to aldophosphamide and subsequent β-elimination; cyclization to produce the 4-hydroxycyclophosphamides, which release phosphorodiamidate by ring opening and elimination; and tautomerization to the enamine with rapid expulsion of phosphorodiamidate.Kinetic studies demonstrated that hydrolysis to the aldehyde contributed minimally to the overall activation process and that the enamine pathway represented the major route of activation.For those analogues that could undergo cyclization this pathway competed effectively with enamine release, and these analogues were essentially equivalent to their 4-hydroxycyclophosphamide counterparts in cytotoxicity.A series of tetra-N-substituted phosphorodiamidates that cannot undergo cyclization was prepared to explore the effects of cyclization on the cytotoxicity of these analogues.The tetrakis(chloroethyl)phosphorodiamidates were highly potent in vitro against both cyclophosphamide-sensitive and -resistant L1210 and P388 cell lines, and one of these analogues had significant antitumor activity against L1210 leukemia in vivo.These results demonstrate that the enamine mechanism provides a viable pathway for delivery of phosphorodiamidates and that this approach can be used to deliver phosphorodiamidates that are non-cross-resistant in cyclophosphamide-resistant cell lines.