Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

686344

Sigma-Aldrich

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

95%

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

signalword

Warning

hcodes

H312,H319

Hazard Classifications

Acute Tox. 4 Dermal - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBB2505V
02396BP
02396BPV
03212DH

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

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