4,4,5,5-tetramethyl-1,3,2λ5-dioxaphospholan-2-one

• ChemBase ID: 141589
• Molecular Formular: C6H13O3P
• Molecular Mass: 164.139381
• Monoisotopic Mass: 164.06023091
• SMILES: CC1(C(OP(=O)O1)(C)C)C
• Canonical SMILES: CC1(C)OP(=O)OC1(C)C
• InChI: InChI=1S/C6H13O3P/c1-5(2)6(3,4)9-10(7)8-5/h10H,1-4H3
• InChIKey: QPONEGYFSLRCLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-1,3,2λ^5-dioxaphospholan-2-one
• IUPAC Traditional name: 4,4,5,5-tetramethyl-1,3,2λ^5-dioxaphospholan-2-one
• Synonyms: HASPO-1; 2-Oxo-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane; 4,4,5,5-Tetramethyl-1,3,2-dioxaphospholan-2-ol; Phosphonic acid pinacol ester; Pinacol phosphonate; 4,4,5,5-Tetramethyl-1,3,2-dioxaphospholane 2-oxide; 2-氧代-4,4,5,5-四甲基-1,3,2-二氧磷杂环戊烷; 4,4,5,5-四甲基-1,3,2-二氧磷杂环戊烷2-氧化物; 膦酸频哪醇酯; 频哪醇膦酸酯; 4,4,5,5-四甲基-1,3,2-二氧磷杂环戊烷-2-醇

Database IDs

• CAS Number: 16352-18-4
• MDL Number: MFCD09836231
• PubChem SID: 162235823
• PubChem CID: 11309699

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.8108
• LogD (pH = 7.4): 0.8108
• Log P: 0.8108
• Molar Refractivity: 37.6817 cm^3
• Polarizability: 15.796553 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99-106 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 21-36
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C6H13O3P

DETAILS

Sigma Aldrich - 686344

Application
Air-stable preligand for Pd-catalyzed Kumada-type cross-couplings.1

• Preligand in palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates with Grignard reagents1
• Catalyst for reversible chain transfer polymerizations2Reactant for:
• Synthesis of oxapalladacycle as catalyst for Markovnikov-type addition3
• Preparation of palladium(II) complexes as catalysts for Heck cross-coupling reactions4
• Preparation of palladium catalysts for asymmetric hydrogenation of a-keto phosphonates 5
• Hydrophosphorylation of alkenes, dienes and enynes in the presence of rhodium catalysts6
Packaging
1 g in glass bottle