4-Ketocyclophosphamide

Base Information

• Chemical Name: 4-Ketocyclophosphamide
• CAS No.: 27046-19-1
• Molecular Formula: C₇H₁₃Cl₂N₂O₃P
• Molecular Weight: 275.072
• NSC Number: 139488
• UNII: N9DU5QVF19
• DSSTox Substance ID: DTXSID501031077
• Nikkaji Number: J78.702G
• Wikidata: Q27105518
• Metabolomics Workbench ID: 67717
• ChEMBL ID: CHEMBL3544546
• Mol file: 27046-19-1.mol

Synonyms:4-ketocyclophosphamide;4-ketocyclophosphamide, (R)-isomer;4-ketocyclophosphamide, (S)-isomer

Chemical Property of 4-Ketocyclophosphamide

Chemical Property:

• Melting Point: 139-141°C
• Boiling Point: °Cat760mmHg
• PKA: 12.02±0.20(Predicted)
• Flash Point: °C
• PSA: 65.65000
• Density: 1.42g/cm³
• LogP: 1.49000
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 274.0040847
• Heavy Atom Count: 15
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

4-OxoCyclophosphamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COP(=O)(NC1=O)N(CCCl)CCCl
• Uses: A minor metabolite of Cyclophosphamide (C988580).

Technology Process of 4-Ketocyclophosphamide

There total 3 articles about 4-Ketocyclophosphamide 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:

cyclophosphamide (50-18-0) → 4-hydroxycyclophosphamide (40277-05-2) + 4-peroxycyclophosphamide (51274-71-6,146566-41-8) + 4-ketocyclophosphamide mustard (27046-19-1,69580-11-6,69580-12-7)

Guidance literature:

With dihydrogen peroxide; iron(II) sulfate; In water; at 0 - 10 ℃;

Reference yield:

cyclophosphamide (50-18-0) → Carboxyphosphamide (22788-18-7) + aldophosphamide (35144-64-0) + 4-hydroxycyclophosphamide (40277-05-2) + 4-ketocyclophosphamide mustard (27046-19-1,69580-11-6,69580-12-7)

Guidance literature:

pharmacokinetics, metabolism;

Reference yield:

N-methoxylamine hydrochloride (593-56-6) + 4-peroxycyclophosphamide (51274-71-6,146566-41-8) → 4-hydroperoxycyclophosphamide (39800-16-3,146566-40-7) + aldophosphamide O-methyloxime (343967-21-5,82084-80-8) + 4-ketocyclophosphamide mustard (27046-19-1,69580-11-6,69580-12-7) + (E)-aldophosphamide O-methyl oxime (82084-80-8)

Guidance literature:

With sodium hydroxide; at 37 ℃; Product distribution; pH 7.4 (lutidine 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