4-HYDROPEROXY CYCLOPHOSPHAMIDE

Base Information

• Chemical Name: 4-HYDROPEROXY CYCLOPHOSPHAMIDE
• CAS No.: 39800-16-3
• Deprecated CAS: 78598-44-4
• Molecular Formula: C₇H₁₅Cl₂N₂O₄P
• Molecular Weight: 293.087
• NSC Number: 181815
• DSSTox Substance ID: DTXSID2049058
• Nikkaji Number: J78.539C
• Wikipedia: Perfosfamide
• Wikidata: Q4637151
• NCI Thesaurus Code: C1423
• Metabolomics Workbench ID: 66919
• ChEMBL ID: CHEMBL61511
• Mol file: 39800-16-3.mol

Synonyms:Hydroperoxide,2-[bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl, P-oxide;4-Hydroperoxycyclofosfamide;4-Hydroperoxycyclophosphamide;Asta 6496;

Chemical Property of 4-HYDROPEROXY CYCLOPHOSPHAMIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-103°C
• Refractive Index: 1.525
• Boiling Point: 419.9 °C at 760 mmHg
• Flash Point: 207.8 °C
• PSA: 80.84000
• Density: 1.46 g/cm³
• LogP: 2.02850
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly), DCM
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 292.0146493
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroperoxycyclophosphamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COP(=O)(NC1OO)N(CCCl)CCCl
• Recent ClinicalTrials: Chemotherapy, Radiation Therapy, Immunotherapy, and Bone Marrow Transplantation in Treating Patients With Neuroblastoma
• Uses: A metabolite of Cyclophosphamide. Antineoplastic; bone marrow purging agent A metabolite of Cyclophosphamide. Antineoplastic; bone marrow purging agent.

Technology Process of 4-HYDROPEROXY CYCLOPHOSPHAMIDE

There total 8 articles about 4-HYDROPEROXY CYCLOPHOSPHAMIDE 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: 70.0%

2-bis(2-chloroethyl)aminotetrahydro-2H-3,4-epoxy<1,3,2>oxazaphosphorine 2-oxide (74307-83-8) → trans-4-hydroperoxycyclophosphamide (39800-16-3,56922-83-9,61903-31-9,62435-42-1,146566-40-7)

Guidance literature:

With water; In dichloromethane; acetone; for 0.5h;

DOI:10.1021/ja00537a054

Reference yield: 27.0%

O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8) → trans-4-hydroperoxycyclophosphamide (39800-16-3,56922-83-9,61903-31-9,62435-42-1,146566-40-7)

Guidance literature:

With dihydrogen peroxide; ozone; In water; acetone; Ambient temperature;

DOI:10.1021/jm00370a008

Reference yield:

N-methoxylamine hydrochloride (593-56-6) + 4-(tert-butylperoxy)cyclophosphamide → 4-hydroperoxycyclophosphamide (39800-16-3,146566-40-7) + aldophosphamide O-methyloxime (343967-21-5,82084-80-8) + (E)-aldophosphamide O-methyl oxime (82084-80-8)

Guidance literature:

With sodium hydroxide; at 37 ℃; Product distribution; pH 7.4 (pyridine buffer, D₂O); decomposition of cyclophosphamide derivatives in the presence of trapping agent O-methylhydroxylamine;

DOI:10.1002/jps.2600710417

upstream raw materials:

cyclophosphamide

N-methoxylamine hydrochloride

4-peroxycyclophosphamide

O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate

Downstream raw materials:

trans-4-hydroxycyclophosphamide

aldophosphamide O-methyloxime

(E)-aldophosphamide O-methyl oxime

4-{2-[bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylsulfanylmethyl}-benzoic acid

Refernces

• 1、 Kwon, Chul-Hoon,Borch, Richard F.,Engel, Jurgen,Niemeyer, Ulf. "Activation Mechanisms of Mafosfamide and the Role of Thiols in Cyclophosphamide Metabolism". . p. 395 - 399. Retrieved 2007/10/02.
• 2、 Borch,Getman. "Base-catalyzed hydrolysis of 4-hydroperoxycyclophosphamide: Evidence for iminocyclophosphamide as an intermediate". . p. 485 - 490. Retrieved 2007/10/02.