4798-75-8

Basic information

• Product Name: phenyl bis(2-chloroethyl)phosphoramidochloridate
• CAS NO: 4798-75-8
• Molecular Formula: C₁₀H₁₃Cl₃NO₂P
• Molecular Weight: 316.5485
• Mol File: 4798-75-8.mol

Chemical Properties

• Boiling Point: 385.5°C at 760 mmHg
• Flash Point: 186.9°C
• Density: 1.385g/cm³
• Vapor Pressure: 3.79E-06mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: phenyl bis(2-chloroethyl)phosphoramidochloridate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl bis(2-chloroethyl)phosphoramidochloridate(4798-75-8)
• EPA Substance Registry System: phenyl bis(2-chloroethyl)phosphoramidochloridate(4798-75-8)

Safety Data

• Hazardous Substances Data: 4798-75-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Phenyl bis(2-chloroethyl)phosphoramidochloridate is used as a reagent in the synthesis of organophosphorus compounds for various applications in the chemical industry.
Used in Pharmaceutical Industry:
Phenyl bis(2-chloroethyl)phosphoramidochloridate is used as a precursor in the synthesis of certain pharmaceutical compounds, particularly those with organophosphorus structures.
Used in Chemical Warfare Agents:
Although its use is strictly regulated and controlled, phenyl bis(2-chloroethyl)phosphoramidochloridate is known for its potential use as a precursor in the synthesis of chemical warfare agents.

Upstream product

• 108-95-2 phenol 
• 127-88-8 N,N-di(2-chloroethyl)amidophosphoric acid dichloride 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 770-12-7 O-phenyl phosphorodichloridate 

Downstream Products

• 98650-19-2 C₁₂H₁₉Cl₂N₂O₂P 
• 1373774-62-9 phenyl N,N-bis(β-chloroethyl)amido(ethoxyphenylalaninyl)phosphate 
• 98650-17-0 C₁₄H₂₃Cl₂N₂O₂P 
• 4798-76-9 Aziridin-phosphonsaeure-(1)-phenylester- 
• 100002-14-0 N,N,N',N'-Tetrakis-(2-chlorethyl)-symm.-pyrophosphorsaeure-diphenylester-diamid 
• 46779-96-8 N,N-bis(2-chloroethyl)phenylphosphoramidic acid 
• 78218-72-1 Phosphorsaeure-<2-chlor-ethylester>-phenylester- 
• 16012-71-8 C₂₀H₃₂Cl₂N₃O₄P 
• 41346-48-9 N,N-bis-(2-chloro-ethyl)-N'-(4-thiazol-2-ylsulfamoyl-phenyl)-phosphorodiamidic acid phenyl ester 
• 41423-53-4 N,N-bis-(2-chloro-ethyl)-N'-(4-methyl-thiazol-2-yl)-phosphorodiamidic acid phenyl ester 
• 20464-96-4 N,N-bis-(2-chloro-ethyl)-P-morpholin-4-yl-phosphonamidic acid phenyl ester 
• 1357142-19-8 2-(4-chlorophenyl)-5,7-dimethoxyquinolin-4-yl phenyl bis(2-chloroethyl)phosphoramidate 
• 1254975-83-1 chrysin-7-yl phenyl N,N-bis(2-chloroethyl) phosphoramidate 

Relevant articles and documents

Novel sophoridine derivatives bearing phosphoramide mustard moiety exhibit potent antitumor activities in vitro and in vivo

Novel mustard functionalized sophoridine derivatives were synthesized and evaluated for their cytotoxicity against of a panel of various cancer cell lines. They were shown to be more sensitive to S180 and H22 tumor cells with IC50 values ranging from 1.01–3.65 μM, and distinctly were more cytotoxic to cancer cells than normal cell L929. In addition, compounds 7a, 7c, and 7e displayed moderate tumor suppression without apparent organ toxicity in vivo against mice bearing H22 liver tumors. Furthermore, they arrested tumor cells in the G1 phase and induced cellular apoptosis. Their potential binding modes with DNA-Top I complex have also been investigated.

Synthesis, cytotoxicity, topoisomerase I inhibition and molecular docking of novel phosphoramide mustard sophoridinic acid analogues

A series of novel phosphoramide mustard sophoridinic acid analogues, consisting of nitrogen mustard group and sophoridinic acid scaffold, have been designed, synthesized and evaluated for their topoisomerase inhibitory activity as well as cytotoxicity against six tumor cell lines (SMMC-7721, LoVo, MCF-7, K562, S180 and H22) and a normal cell line (L929). Among the compounds tested, five were found to be potent inhibitors and exhibited potent cytotoxicity against S180 and H22 cell lines with IC50 values of 1–4?μM. Further mechanistic studies showed that this class of compounds acted as novel topoisomerase I (Topo I) catalytic inhibitors by preventing the binding of Topo I to DNA and inhibiting the cleavage of DNA, and molecular docking studies revealed that the binding energy for these compounds was comparable to that for classic Topo I inhibitors CPT and HCPT, indicating that the compounds have an interaction with DNA and Topo I.

Preparation method and use of quinolizidine alkaloid derivative

The invention provides a quinolizidine alkaloid derivative with high activity, low toxicity and good antitumor performance. The derivative is formed by merging a targeting quinolizidine alkaloid group and a highly-active chlormethine group in one molecule

Synthesis of some cyclophosphorodiamidates derivatives of bis(2-chloroethyl)amine

Phenyl phosphorodichloridate (1) is readily prepared by reaction of phenol with phosphoryl chloride at low temperature. The crude product is white in colour is subjected to vacuum distillation. However, this reagent reacts only poorly with bis(2-chloroethyl)amine hydrochloride at ambient temperature; thus, an alternative route was sought to aniline and to give 2 and 3, respectively compounds. Compound (3) reacted with aniline and diazabicyclo[2,2,2]octane in refluxing toluene to give 4. Reaction of 3 with diazabicyclo[2,2,2]octane and potassium tert-butoxide in refluxing toluene gave 5 and 6, respectively which compound 6 arised from elimination of HCl from the 2-chloroethyl group of compound 5. Reactions proceed in high yield, under mild conditions. The structures of prepared compounds were confirmed by 1H, 31P and 13C NMR spectroscopy, mass spectrometry and X-ray crystallography.

Synthesis of ethyl and phenyl amido(ethoxyphenylalaninyl)phosphate compounds

The synthetic route for preparation of three phosphoramides containing amino acid and their precursors in good yield and mild conditions is reported. This involved the synthesis of the ethyl and phenyl phosphorodichloridate and its reaction with bis(β-chloroethyl) amine or diethylamine, followed by the reaction of the products with phenyl alanine ethyl ester hydrochloride. In all the three compounds, because of the presence of chiral centre, the final products were obtained as a mixture of two diastereoisomers, which can be determined using 31P NMR and TLC methods. The structures of all the prepared compounds were confirmed by 1H NMR, 31P NMR, 13C NMR spectroscopy.

A convenient synthesis of chrysin-7-yl aryl N-bis(2-chloroethyl) phosphoramidate

A series of novel chrysin-7-yl aryl N-bis(2-chloroethyl) phosphoramidates have been synthesised in good yield via phosphorylation reactions and their structures were elucidated by IR, NMR and elemental analysis.

Protease-mediated enzymatic hydrolysis and activation of aryl phosphoramidate derivatives of stavudine

Several proteases are capable of hydrolyzing the aryl substituted phosphoramidate derivatives of stavudine resulting in the formation of the active metabolite, alaninyl d4T monophosphate. Subtilisin Protease A, Subtilisin Griseus, Subtilisin Carlsberg, Papaya, Bacillus were amongst the most effective proteases in hydrolyzing stavudine derivatives and specificity of their activity was confirmed using several protease inhibitors to block the hydrolysis of these phosphoramidate derivatives. We found that these proteases exhibit chiral selectivity at the phosphorus center of stavudine derivatives. Our results indicate that cellular proteases may be responsible for the activation of these phosphoramidate derivatives. In addition, we show that the enzymatic hydrolysis takes place at the carboxymethyl ester side chain of these pro-drugs and the direct attack on the phosphorus center by these enzymes does not occur. Finally, we describe a novel activation pathway hitherto unknown for the activation and viral inhibitory characteristic shown by these phosphoramidate derivatives of stavudine.

Lipase-mediated stereoselective hydrolysis of stampidine and other phosphoramidate derivatives of stavudine

Enzymatic hydrolysis of stampidine and other aryl phosphate derivatives of stavudine were investigated using the Candida Antarctica Type B lipase. Modeling studies and comparison of the hydrolysis rate constants revealed a chiral preference of the lipase

PHENYL N-BIS(2-CHLOROETHYL)-N'-PHENYLPHOSPHORODIAMIDATE (1): CRYSTAL STRUCTURE AND APPARENT 31P-13C COUPLING ANOMALIES

The title compound (1) was synthesized by reacting phenyl phosphorodichloridate with bis(2-chlorethyl)amine hydrochloride to form 2 in 89-92percent yield followed by reaction of 2 with aniline to form 1 in 62percent yield. 1 crystallizes from benzene as a