benzyl 3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoate

• ChemBase ID: 163719
• Molecular Formular: C14H21Cl2N2O4P
• Molecular Mass: 383.207301
• Monoisotopic Mass: 382.06159915
• SMILES: C(OP(=O)(N(CCCl)CCCl)N)CC(=O)OCc1ccccc1
• Canonical SMILES: ClCCN(P(=O)(OCCC(=O)OCc1ccccc1)N)CCCl
• InChI: InChI=1S/C14H21Cl2N2O4P/c15-7-9-18(10-8-16)23(17,20)22-11-6-14(19)21-12-13-4-2-1-3-5-13/h1-5H,6-12H2,(H2,17,20)
• InChIKey: URRQYEVJTAKGKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoate
• IUPAC Traditional name: benzyl 3-{[amino(bis(2-chloroethyl)amino)phosphoryl]oxy}propanoate
• Synonyms: 3-[[Amino[bis(2-chloroethyl)amino]phosphinyl]oxy]propanoic Acid Phenylmethyl Ester; 3-[[Amino[bis(2-chloroethyl)amino]phosphinyl]oxy]propanoic Acid Benzyl Ester; Carboxyphosphamide Benzyl Ester

Database IDs

• CAS Number: 37979-67-2
• PubChem SID: 162257854
• PubChem CID: 314986

CALCULATED PROPERTIES

• Acid pKa: 14.420391
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5698
• LogD (pH = 7.4): 1.5698
• Log P: 1.5698
• Molar Refractivity: 90.8507 cm^3
• Polarizability: 36.248997 Å^3
• Polar Surface Area: 81.86 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - C181355

Intermediate in the production of Cyclophosphamide metabolites.

REFERENCES

• Takamizawa, A., et al.: Chem. Pharm. Bull., 20, 1612 (1972)