phenoxy(phenylamino)phosphinoyl chloride

• ChemBase ID: 103453
• Molecular Formular: C12H11ClNO2P
• Molecular Mass: 267.648001
• Monoisotopic Mass: 267.02159291
• SMILES: ClP(=O)(Nc1ccccc1)Oc1ccccc1
• Canonical SMILES: ClP(=O)(Oc1ccccc1)Nc1ccccc1
• InChI: InChI=1S/C12H11ClNO2P/c13-17(15,14-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H,(H,14,15)
• InChIKey: ZUQYQPGYEFBITH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenoxy(phenylamino)phosphinoyl chloride
• IUPAC Traditional name: phenoxy(phenylamino)phosphinoyl chloride
• Synonyms: 3P-Cl; Phenyl N-Phenyl-chlorophosphoramidate; PHENYL N-PHENYL-PHOSPHORAMIDOCHLORIDATE; N-Phenylphosphoramidochloridic acid phenyl ester; Phenyl N-phenylphosphoramidochloridate; Phenyl phenylphosphoramidochloridate; N-苯基磷氨基氯化苯

Database IDs

• CAS Number: 51766-21-3
• EC Number: 257-400-5
• MDL Number: MFCD00003029
• PubChem SID: 162090596; 24850351
• PubChem CID: 103959

CALCULATED PROPERTIES

• Acid pKa: 12.384188
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.0879624
• LogD (pH = 7.4): 3.0879662
• Log P: 3.0879703
• Molar Refractivity: 68.6932 cm^3
• Polarizability: 26.88193 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 132-134 °C(lit.)

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; 95+%
• Linear Formula: C6H5NHP(O)(Cl)OC6H5

DETAILS

MP Biomedicals - 02151842

Crystalline
Phosphorylation reagent for oligonucleotide synthesis.

Sigma Aldrich - 174602

Packaging
5 g in glass bottle
Application
Reactant for synthesis of:
• Resin-immobilized actinide ligands1
• Carboxylic acid anhydrides and their derivatives2
• Thiadiaminooxopyrimidine derivatives for antitumor activity3
• Polyanhydrides via dehydrative coupling agents4Reactant for:
• One-pot conversion of pyrimidinones to pyrimidines5
• Conversion to alkyl Ph diester6Catalyst for polymerization reactions7Involved in biological studies for chymotrypsin binding and inhibition8

REFERENCES

• Synthesis, 185 (1976).
• Chem. Commun., 772 (1976).