3-(2-chloroethyl)-2-[(2-chloroethyl)amino](4,4,5,5-2H4)-1,3,2λ5-oxazaphosphinan-2-one

• ChemBase ID: 171521
• Molecular Formular: C7H15Cl2N2O2P
• Molecular Mass: 261.085961
• Monoisotopic Mass: 260.02481972
• SMILES: O1CCCN(P1(=O)NCCCl)CCCl
• Canonical SMILES: ClCCNP1(=O)OCCCN1CCCl
• InChI: InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
• InChIKey: HOMGKSMUEGBAAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-chloroethyl)-2-[(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: 3-(2-chloroethyl)-2-[(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• Synonyms: N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-Oxide-d4; A 4942-d4; Asta Z 4942-d4; Cyfos-d4; Holoxan-d4; Ifex-d4; Ifomide-d4; Iphosphamide-d4; MJF 9325-d4; Mitoxana-d4; NSC 109724-d4; Naxamide-d4; Ifosfamide-d4

Database IDs

• CAS Number: 1189701-13-0
• PubChem SID: 164227431
• PubChem CID: 46781940

CALCULATED PROPERTIES

• Acid pKa: 12.388063
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.09654763
• LogD (pH = 7.4): 0.09654373
• Log P: 0.096547686
• Molar Refractivity: 58.4781 cm^3
• Polarizability: 23.373835 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Semi Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I265002

A cytostatic agent, related structurally to cyclophosphamide.

REFERENCES

• Creaven, P. J., et al.: Cancer Treat. Rep., 60, 445(1976)
• Schoenike, S. E., Clin. Pharm., 9, 179(1976)
• Skinner, R., et al.: J. Clin. Oncol., 11, 173 (1993).