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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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ8427
SHBJ3444
SHBH5553V
SHBG7553V
SHBF9423V

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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)
PdI2-Catalyzed Regioselective Cyclocarbonylation of 2-Allyl Phenols to Dihydrocoumarins
Ame?zquita-Valencia M and Alper H
Organic Letters, 16(22), 5827-5829 (2014)
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)
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)

Articles

Trialkylphosphine for Morita-Baylis Hillman Reactions

The use of amines and phosphines in nucleophilic catalysis is well precedented; however, arguably one of the severe limitations with respect to exploiting the more nucleophilic, yet less basic, phosphine in this regard is its air sensitivity.

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