1-{[(diphenylphosphanyl)methyl]sulfanyl}ethan-1-one borane

• ChemBase ID: 141003
• Molecular Formular: C15H18BOPS
• Molecular Mass: 288.152581
• Monoisotopic Mass: 288.09090323
• SMILES: B.CC(=O)SCP(c1ccccc1)c1ccccc1
• Canonical SMILES: CC(=O)SCP(c1ccccc1)c1ccccc1.B
• InChI: InChI=1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3
• InChIKey: MXPNVFCCEGQGEN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(diphenylphosphanyl)methyl]sulfanyl}ethan-1-one borane
• IUPAC Traditional name: 1-{[(diphenylphosphanyl)methyl]sulfanyl}ethanone borane
• Synonyms: Acetylthiomethyl-diphenylphosphine borane complex; 乙酰基硫甲基-硼烷二苯基膦复合物

Database IDs

• CAS Number: 446822-71-5
• PubChem SID: 162235239
• PubChem CID: 11266195

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.0731
• LogD (pH = 7.4): 4.0731
• Log P: 4.0731
• Molar Refractivity: 78.6303 cm^3
• Polarizability: 31.359432 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 52-55 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0%
• Empirical Formula (Hill Notation): C15H18BOPS

DETAILS

Sigma Aldrich - 670359

Packaging
1 g in glass bottle
250 mg in glass bottle
Legal Information
Sold under license for research and development purposes only. US Patent 6,974,884 and related patents apply
Application

• Traceless Staudinger ligation reagent with borane protecting group.
• The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.1
• After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.2
• Used in the synthesis of cyclic peptides.2