Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

695459

Sigma-Aldrich

1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane

97%

Synonym(s):

1,3,5,7-Tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane, meCgPPh

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C16H21O3P
CAS Number:
97739-46-3
Molecular Weight:
292.31
UNSPSC Code:
12352005
PubChem Substance ID:
329761744
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

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
reaction type: Cross Couplings

mp

106-111 °C

functional group

phosphine

SMILES string

CC12CC3(C)OC(C)(CC(C)(O1)P3c4ccccc4)O2

InChI

1S/C16H21O3P/c1-13-10-15(3)19-14(2,17-13)11-16(4,18-13)20(15)12-8-6-5-7-9-12/h5-9H,10-11H2,1-4H3

InChI key

AVVSJWUWBATQBX-UHFFFAOYSA-N

Application

1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane can be used:
  • As a ligand to synthesize complexes for hydroformylation catalysis.
  • To catalyze the synthesis of dibenzo[b,f][1,4]oxazepin-11(10H)-ones and 3-methyl-3,4-dihydrocoumarins by intramolecular cyclocarbonylation.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBJ8427
SHBJ3444
SHBH5553V
SHBG7553V
SHBF9423V

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

PdI2-Catalyzed Regioselective Cyclocarbonylation of 2-Allyl Phenols to Dihydrocoumarins
Ame?zquita-Valencia M and Alper H
Organic Letters, 16(22), 5827-5829 (2014)
Phenylphosphatrioxa-adamantanes: bulky, robust, electron-poor ligands that give very efficient rhodium (I) hydroformylation catalysts
Baber RA, et al.
Dalton Transactions, 6, 1079-1085 (2005)
Synthesis of Dibenzo [b, f][1, 4] oxazepin-11 (10 H)-ones via Intramolecular Cyclocarbonylation Reactions Using PdI2/Cytop 292 as the Catalytic System
Yang Q, et al.
The Journal of Organic Chemistry, 75(18), 6297-6299 (2010)
Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
Pittaway R, et al.
Organic Letters, 19(11), 2845-2848 (2017)

Articles

Trialkylphosphine for MBH Reactions

Amines and phosphines in nucleophilic catalysis are discussed, addressing the air sensitivity of phosphines.

Trialkylphosphine for MBH Reactions

Amines and phosphines in nucleophilic catalysis are discussed, addressing the air sensitivity of phosphines.

Trialkylphosphine for MBH Reactions

Amines and phosphines in nucleophilic catalysis are discussed, addressing the air sensitivity of phosphines.

Trialkylphosphine for MBH Reactions

Amines and phosphines in nucleophilic catalysis are discussed, addressing the air sensitivity of phosphines.

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