1445-38-1

Usage

Uses

Used in Pharmaceutical Synthesis:
Diethyl anilinophosphonate is used as a key intermediate in the production of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
DIETHYL ANILINOPHOSPHONATE serves as an essential building block in the synthesis of various organic compounds, facilitating the creation of a wide range of chemical products.
Used in Flame Retardants:
Diethyl anilinophosphonate is employed as a phosphorus-based flame retardant in the manufacturing process of polymers and plastics, enhancing their fire resistance and safety properties.
Used in Industrial and Laboratory Settings:
Due to its potential hazards, diethyl anilinophosphonate is used under strict safety regulations in industrial and laboratory settings to ensure the protection of workers and the environment.

InChI:InChI=1/C10H16NO3P/c1-3-13-15(12,14-4-2)11-10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3,(H,11,12)

Upstream product

• 64-17-5 ethanol 
• 6955-57-3 phenylamidophosphoric dichloride 
• 2397-47-9 triethyl N-phenylphosphorimidate 
• 814-49-3 diethyl chlorophosphate 
• 62-53-3 aniline 
• 75-62-7 Bromotrichloromethane 
• 141-78-6 ethyl acetate 
• 762-04-9 phosphonic acid diethyl ester 
• 558-13-4 carbon tetrabromide 
• 1186-08-9 diethoxyoxophosphoranesulfenyl chloride 
• 122-52-1 triethyl phosphite 
• 589-57-1 diethyl phosphorylchloridite 
• 5156-98-9 diethyl phenylphosphoramidite 
• 3848-51-9 phenyl-amidophosphoric acid diphenyl ester 

Downstream Products

• 1126-78-9 N-(n-butyl)aniline 
• 61278-91-9 diethyl butyl(phenyl)phosphoramidate 
• 55560-23-1 C₁₈H₂₈NO₆P 
• 25626-89-5 O,O-diethyl-N-ethyl-N-phenyl-phosphoramidate 
• 14303-52-7 Phenylimino-phenylaethylketen 
• 90972-67-1 Diaethyl-N-chlor-N-phenylphosphoramidat 
• 63542-04-1 O-ethyl N-phenylphosphoramidic acid 
• 7006-55-5 diethyl benzyl(phenyl)phosphoramidate 
• 15942-13-9 allyl-phenyl-amidophosphoric acid diethyl ester 
• 2404-05-9 O,O-diethyl S-methyl phosphorothioate 
• 103-72-0 phenyl isothiocyanate 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 142009-78-7 N-phenyl-1,10-phenanthroline-5,6-quinone monoimine 
• 19738-40-0 diethylester of N,N'-diphenylamidinophosphinic acid 

Relevant academic research and scientific papers

Direct Conversion of Diethyl Hydrogen Phosphate into Diethyl Phosphoramides

The effective, one-step transformation of diethyl hydrogen phosphate into diethyl phosphoramides by using hexamethyltriaminodibromophosphorane prepared "in situ" is described. - Keywords: Hexamethyltriaminodibromophosphorane; Intermolecular dehydration

[{ReH2(PMePH2)2}2(μ-H) 3]-: The first member of a new class of anionic polyhydride dimers [Re2H7L4]-

[K(Q)][{ReH2(PMePh2)2}2(μ-H) 3] is prepared by treatment of {ReH2(PMePh2)2}2)μ-H) 4 with potassium hydride and a crown ether (Q = 18-crown-6 or 1,10-diaza-18-crown-6). The [K(1,10 diaza-18-crown-6)]+ salt contains NH···HRe protonic - hydridic bonds and has been characterized by 31P NMR, variable temperature 1H NMR, IR, and X-ray crystallography. The pKαTHF = 33 of {ReH2(PMePh2)2}2(μ-H) 4 was determined on the basis of its reaction with [K(2,2,2-crypt)][PO(OEt)2NPh.

Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates

A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.

The Step-Wise Synthesis of Oligomeric Phosphoramidates

In this study, the step-wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N?P?N, symmetric and asymmetric P?N?P and P?N?P?N?P linkages. Salt elimination and lithiation strategies were employed to create the new P?N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P?N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.

Evaluation and development of methodologies for the synthesis of thiophosphinic acids

Thiophosphorus acids R1R2P(S)OH constitute an important class of organophosphorus compounds, in which the phosphorus atom is intrinsically chiral if R1 ≠ R2. In connection with a project aimed at the preparation of chiral thiophosphorus acids, various available literature methods were considered, but few fit the requirement of odorless reagents. Herein, the results of our studies on the synthesis of thiophosphinic acids are reported. Ultimately, two major approaches were selected: (1) the Stec reaction of phosphorus amides with carbon disulfide; and (2) the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur. An application to the preparation of a potential chiral phosphorus organocatalyst is also reported.

Synthesis of N-Substituted phosphoramidic acid esters as “reverse” fosmidomycin analogues

An efficient synthetic pathway to a series of novel “reverse” fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial “pro-drugs”.

Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton-Todd Reaction under Base-Free Conditions

A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton-Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.

On the rearrangement of N-aryl-N-Boc-phosphoramidates to N-Boc-protected o-aminoarylphosphonates

Abstract: Various arylamines were converted in two steps to N-Boc-N-arylphosphoramidates. LiTMP and LDA induced directed ortho-metalation at temperatures from ?78 to 0?°C. The ensuing [1,3]-migration of the phosphorus atom with its substituents from the n

Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR)3 and its synthetic applications

A systematic study on the iodine-mediated phosphoramidation reaction of amines and trialkyl phosphites was conducted, which not only disclosed the factors affecting the reaction but also revealed that it could proceed smoothly in CH2Cl2 at room temperature in open air. Using this method, various phosphoramidates with different aliphatic amines and aromatic amines were synthesized in good to excellent yields. Our present investigation shows that this underused method is actually a mild, practical and general way to synthesize phosphoramidates and will have wide applications.

Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate

A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.