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708275

Sigma-Aldrich

1,3-Bis-(2,6-diisopropylphenyl)-[1,3,2]diazaphospholidine 2-oxide

97%

Synonym(s):

1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3,2-diazaphospholidine 2-oxide

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About This Item

Empirical Formula (Hill Notation):
C26H39N2OP
CAS Number:
854929-36-5
Molecular Weight:
426.57
MDL number:
MFCD14708169
UNSPSC Code:
12352005
PubChem Substance ID:
329762783

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

mp

205-210 °C

functional group

phosphine

SMILES string

CC(C)c1cccc(C(C)C)c1N2CCN(c3c(cccc3C(C)C)C(C)C)[PH]2=O

InChI

1S/C26H39N2OP/c1-17(2)21-11-9-12-22(18(3)4)25(21)27-15-16-28(30(27)29)26-23(19(5)6)13-10-14-24(26)20(7)8/h9-14,17-20,30H,15-16H2,1-8H3

InChI key

SQYNIVDXVZPMLW-UHFFFAOYSA-N

Application

Reactnat for synthesis of air-stable palladium HASPO complexes

Catalyst for:
  • Dehydrative direct arylations of arenes
  • Aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds
Ligand used with ruthenium for dehydrative direct arylation of arenes with phenols

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Lutz Ackermann et al.
Organic letters, 10(21), 5043-5045 (2008-10-16)
Phenols can be employed as proelectrophiles in operationally simple ruthenium-catalyzed dehydrative direct arylations, proceeding through chemo- and regioselective functionalizations of C-H and C-OH bonds.

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