105307-66-2

Basic information

• Product Name: N-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
• Synonyms: 2H-1,3,2-oxazaphosphorin-2-amine, N-(2-chloroethyl)tetrahydro-, 2-oxide
• CAS NO: 105307-66-2
• Molecular Formula: C₅H₁₂ClN₂O₂P
• Molecular Weight: 198.5877
• Mol File: 105307-66-2.mol

Chemical Properties

• Boiling Point: 272.1°C at 760 mmHg
• Flash Point: 118.4°C
• Density: 1.3g/cm³
• Vapor Pressure: 0.0062mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: N-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide(105307-66-2)
• EPA Substance Registry System: N-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide(105307-66-2)

Safety Data

• Hazardous Substances Data: 105307-66-2(Hazardous Substances Data)

Upstream product

• 72578-68-8 (2-chloro-ethyl)-[(S)-2-oxo-3-((R)-1-phenyl-ethyl)-2λ⁵-[1,3,2]oxazaphosphinan-2-yl]-amine 
• 72578-67-7 (2-chloro-ethyl)-[(R)-2-oxo-3-((R)-1-phenyl-ethyl)-2λ⁵-[1,3,2]oxazaphosphinan-2-yl]-amine 
• 870-24-6 2-chloroethanamine hydrochloride 
• 156-87-6 propan-1-ol-3-amine 
• 50-18-0 cyclophosphamide 
• 119670-13-2 3-chloroacetyltetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide 
• 72578-61-1 (R)-2-aziridin-1-yl-3-((R)-1-phenyl-ethyl)-[1,3,2]oxazaphosphinane 2-oxide 
• 5638-58-4 2-chloro-2-oxo-1,3,2λ⁵-oxazaphosphinane 

Downstream Products

• 72578-71-3 3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide 

Relevant articles and documents

Characterization of the cytochrome P450 involved in side-chain oxidation of cyclophosphamide in humans

Objective: Cyclophosphamide (CP) is an antineoplastic prodrug which requires bioactivation (4-hydroxylation) by the cytochrome P450 (CYP) enzymes in human liver. In parallel, P450-mediated side-chain oxidation (N-dealkylation) leads to the formation of the non-alkylating dechloroethylcyclophosphamide (DCl-CP) and chloroacetaldehyde, the latter being a potential neurotoxic agent. The enzyme responsible for side-chain oxidation has not been identified yet. We therefore used an in vitro approach to characterize the enzyme involved in N-dealkylation of CP. Methods: CP was incubated with the microsomal fraction of human liver in the presence of specific inhibitors for some P450 enzymes and in the presence of stable expressed P450 enzymes. Dechloroethylcyclophosphamide was analysed using gas chromatography and nitrogen-phosphorus detection. Results: Formation of DCl-CP increased linearly with substrate concentration over the entire concentration range (20 μmol·l-1 to 36 mmol·l-1). Saturation of the enzyme was not observed. Incubation with stable expressed P450 enzymes and inhibition experiments indicated that CYP 3A4 was the major enzyme involved in side-chain oxidation of CP. Conclusion: Our in vitro data indicate that side-chain oxidation of CP occurs in dose-dependent fashion in men with no saturation of this pathway even following dose escalation. Thus enhanced neurotoxicity following CP administration may result in the setting of high-dose chemotherapy. Moreover, we conclude that CP has the potential to interact with other CYP 3A4 substrates.

Synthetic method of cyclophosphamide

The invention relates to the technical field of cyclophosphamide, in particular to a synthetic method of cyclophosphamide. The defects of low yield and high cost existing in the prior art are solved. The synthetic method includes the following methods: S1: simultaneously adding 3-aminopropanol and triethylamine into a phosphorus oxychloride solution and obtaining 2-chlorotetrahydro-2H-1,3,2-oxynitrogen phosphorus heterocyclohexene-2-oxide through mixing; S2: reacting 2-chlorotetrahydro-2H-1,3,2-oxynitrogen phosphorus heterocyclohexene-2-oxide with 2-chloroethylamine hydrochloride to obtain 2-[(2-chlormethine)amidogen]tetrahydrogen-2H-1,3,2-oxynitrogen phosphorus heterocyclohexene-2-oxide; simultaneously adding 3-aminopropanol and triethylamine into the phosphorus oxychloride solution, reversing an original preparation process, improving yield; and adding sodium borohydride/concentrated sulfuric acid into 3-(2-chloracetyl group)-2-[(2-chlormethine)amidogen]tetrahydrogen-2H-1,3,2-oxynitrogen phosphorus heterocyclohexene-2-oxide. Thus, yield value of the step is improved and the total yield is further improved.

Synthesis of potential metabolites of (S)-(-)-bromofosfamide

(S)-(-)-Bromofosfamide, a newly obtained anticancer agent, recently became a subject of phase I clinical trials in Poland. With the aim to study its metabolism in humans using phosphorus nuclear magnetic resonance a group of potential metabolites of this agent was synthesized.

Analysis of the urinary excretion of ifosfamide and its N-dechloroethylated metabolites in children using 31P-NMR spectroscopy

Amounts of ifosfamide (GAS 3778-73-2) and its N-dechloroethylated metabolites excreted in the urine were measured using 31P-NMR spectroscopy in 26 cancer children treated with this drug. Strong inter-patient variation in levels of these compoun