3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide

Base Information

• Chemical Name: 3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide
• CAS No.: 72578-71-3
• Molecular Formula: C7H13N2PO3Cl2
• Molecular Weight: 275.072
• Mol file: 72578-71-3.mol

Synonyms:3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide;IFOSFAMIDEACYLATE;(R)-2-Chloro-1-(2-((2-chloroethyl)amino)-2-oxido-1,3,2-oxazaphosphinan-3-yl)ethanone;3-(2-CHLOROACETYL)-2-[(2-CHLOROETHYL)AMINO]TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORINE-2-OXIDE;IfofaMide acylation objects;

Chemical Property of 3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide

Chemical Property:

• Refractive Index: 1.48
• Boiling Point: 355.0±52.0 °C(Predicted)
• PKA: -1.29±0.20(Predicted)
• PSA: 68.45000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 1.73940
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-Chloro-1-(2-((2-chloroethyl)amino)-2-oxido-1,3,2-oxazaphosphinan-3-yl)ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-2-Chloro-1-(2-((2-chloroethyl)amino)-2-oxido-1,3,2-oxazaphosphinan-3-yl)ethanone is an intermediate in the preparation of Ifosfamide (I265000), a cytostatic agent, related structurally to cyclophosphamide. antineoplastic agent and antimetabolite

Technology Process of 3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide

There total 4 articles about 3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-2-aziridin-1-yl-3-((R)-1-phenyl-ethyl)-[1,3,2]oxazaphosphinane 2-oxide (72578-61-1) → 3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide (72578-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl / diethyl ether

2: H₂ / Pd-C / ethanol

3: tetrahydrofuran

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol;

DOI:10.1021/ja00520a015

Reference yield:

(2-chloro-ethyl)-[(S)-2-oxo-3-((R)-1-phenyl-ethyl)-2λ5-[1,3,2]oxazaphosphinan-2-yl]-amine (72578-68-8) → 3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide (72578-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / ethanol

2: tetrahydrofuran

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00520a015

Reference yield:

(2-chloro-ethyl)-[(R)-2-oxo-3-((R)-1-phenyl-ethyl)-2λ5-[1,3,2]oxazaphosphinan-2-yl]-amine (72578-67-7) → 3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide (72578-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / ethanol

2: tetrahydrofuran

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00520a015

upstream raw materials:

Dechloroethylcyclophosphamide

chloroacetyl chloride

(R)-2-aziridin-1-yl-3-((R)-1-phenyl-ethyl)-[1,3,2]oxazaphosphinane 2-oxide

(2-chloro-ethyl)-[(S)-2-oxo-3-((R)-1-phenyl-ethyl)-2λ⁵-[1,3,2]oxazaphosphinan-2-yl]-amine

Downstream raw materials:

ilfosfamide