Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

686344

Sigma-Aldrich

4,4,5,5-Tetramethyl-1,3,2-dioxaphospholane 2-oxide

95%

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
2-Oxo-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, 4,4,5,5-Tetramethyl-1,3,2-dioxaphospholan-2-ol, HASPO-1, Phosphonic acid pinacol ester, Pinacol phosphonate
Empirical Formula (Hill Notation):
C6H13O3P
CAS Number:
16352-18-4
Molecular Weight:
164.14
MDL number:
MFCD09836231
UNSPSC Code:
12352005
PubChem Substance ID:
329761040

Assay

95%

form

powder

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

mp

99-106 °C

functional group

phosphine

SMILES string

CC1(C)O[PH](=O)OC1(C)C

InChI

1S/C6H13O3P/c1-5(2)6(3,4)9-10(7)8-5/h10H,1-4H3

InChI key

QPONEGYFSLRCLJ-UHFFFAOYSA-N

Application

  • Preligand in palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates with Grignard reagents
  • Catalyst for reversible chain transfer polymerizations

Reactant for:
  • Synthesis of oxapalladacycle as catalyst for Markovnikov-type addition
  • Preparation of palladium(II) complexes as catalysts for Heck cross-coupling reactions
  • Preparation of palladium catalysts for asymmetric hydrogenation of a-keto phosphonates
  • Hydrophosphorylation of alkenes, dienes and enynes in the presence of rhodium catalysts
Air-stable preligand for Pd-catalyzed Kumada-type cross-couplings.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H312,H319

Hazard Classifications

Acute Tox. 4 Dermal - Eye Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Lutz Ackermann et al.
Organic letters, 8(16), 3457-3460 (2006-07-28)
[reaction: see text] Air-stable and easily accessible PinP(O)H enables highly efficient palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates. The in situ generated catalyst proved applicable not only to electron-rich and electron-poor carbocyclic tosylates but also to heterocyclic tosylates, such as

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service