4-hydroxycyclophosphamide

Base Information

• Chemical Name: 4-hydroxycyclophosphamide
• CAS No.: 40277-05-2
• Molecular Formula: C7H15Cl2N2O3P
• Molecular Weight: 277.087
• Hs Code.: 2934999090
• NSC Number: 196562
• UNII: 1XBF4E50HS
• DSSTox Substance ID: DTXSID90960669
• Nikkaji Number: J65.704B
• Wikipedia: 4-Hydroxycyclophosphamide
• Wikidata: Q15711643
• Metabolomics Workbench ID: 52872
• ChEMBL ID: CHEMBL731
• Mol file: 40277-05-2.mol

Synonyms:4-Hydroperoxydechlorocyclophosphamide;4-Hydroxycyclophosphamid;4-OH cyclophosphamide;4-Hydroxycyclophosphamide;2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ⁵-oxazaphosphinan-4-ol;

Chemical Property of 4-hydroxycyclophosphamide

Chemical Property:

• Vapor Pressure: 1.37E-07mmHg at 25°C
• Boiling Point: 387.1°Cat760mmHg
• Flash Point: 187.9°C
• PSA: 71.61000
• Density: 1.42g/cm³
• LogP: 1.53120
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 276.0197347
• Heavy Atom Count: 15
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

4-HYDROXY CYCLOPHOSPHAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COP(=O)(NC1O)N(CCCl)CCCl

Technology Process of 4-hydroxycyclophosphamide

There total 26 articles about 4-hydroxycyclophosphamide 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: 32.0%

cyclophosphamide (50-18-0) → 4-hydroxycyclophosphamide (40277-05-2)

Guidance literature:

With dihydrogen peroxide; unspecific peroxygenase of Marasmius rotula; In aq. acetate buffer; at 25 ℃; for 1h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1186/s13568-020-01064-w

Reference yield:

cis-4-Hydroperoxycyclophosphamide (56922-83-9) → cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2)

Guidance literature:

With dimethylsulfide; In methanol; for 0.0833333h;

DOI:10.1021/jm00127a016

Reference yield:

O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8) → cis-4-hydroxycyclophosphamide (61903-29-5,88852-77-1,40277-05-2,61903-30-8,88852-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / ozone, 30percent aq. H₂O₂ / acetone; H₂O / Ambient temperature

2: Ph₃P / CH₂Cl₂ / 0.25 h / Ambient temperature

With dihydrogen peroxide; ozone; triphenylphosphine; In dichloromethane; water; acetone;

DOI:10.1021/jm00370a008

upstream raw materials:

cyclophosphamide

4-hydroperoxycyclophosphamide

iminocyclophosphamide

aldophosphamide

Downstream raw materials:

aldophosphamide

aldophosphamide hydrate

trans-4-hydroxycyclophosphamide

trans-4-hydroxycyclophosphamide

Refernces

• 1、 Van der Steen,Timmer,Westra,Benckhuysen. "4-hydroperoxidatin in the Fenton oxidation of the antitumor agent cyclophosphamide.". . p. 7535 - 7536. Retrieved 1973.
• 2、 K?nig, Rosalie,Küpper, Jan-Heiner,Kammerer, Sarah,Kiebist, Jan,Scheibner, Katrin,Schmidtke, Kai-Uwe,Steinbrecht, Susanne,Thiessen, Markus. "Synthesis of cyclophosphamide metabolites by a peroxygenase from Marasmius rotula for toxicological studies on human cancer cells". . . Retrieved 2020.
• 3、 Kwon,Borch. "Effects of N-substitution of the activation mechanisms of 4-hydroxycyclophosphamide analogues". . p. 1491 - 1496. Retrieved 2007/10/02.