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Merck
CN

745324

Sigma-Aldrich

Bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine

≥96.5% (elemental analysis)

Synonym(s):

Bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphane, trop2-PPh

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About This Item

Empirical Formula (Hill Notation):
C36H27P
CAS Number:
1204348-65-1
Molecular Weight:
490.57
Beilstein:
20018338
MDL number:
MFCD22666426
UNSPSC Code:
12352002
PubChem Substance ID:
329764975
NACRES:
NA.22

Key Documents

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Assay

≥96.5% (elemental analysis)

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

loss

≤2.0% loss on drying

functional group

phosphine

SMILES string

c1ccc(cc1)P(C2c3ccccc3C=Cc4ccccc24)C5c6ccccc6C=Cc7ccccc57

InChI

1S/C36H27P/c1-2-16-30(17-3-1)37(35-31-18-8-4-12-26(31)22-23-27-13-5-9-19-32(27)35)36-33-20-10-6-14-28(33)24-25-29-15-7-11-21-34(29)36/h1-25,35-36H

InChI key

FPKRJQIFIQXPKV-UHFFFAOYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBH7088V
BCBH7089
BCBH7088

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Catalyzed Dehydrogenative Coupling of Primary Alcohols with Water, Methanol, or Amines
Zweifel, T., et al.
Angewandte Chemie (International Edition in English), 49, 559-563 (2009)
Electromeric rhodium radical complexes.
Florian Frank Puschmann et al.
Angewandte Chemie (International ed. in English), 49(2), 385-389 (2009-12-04)
Torsten Büttner et al.
Chemical communications (Cambridge, England), 24(24), 2820-2821 (2004-12-16)
A combination of the rigid bis(5H-dibenzo[a,d]cyclohepten-5-yl)amine (trop(2)NH) and 5-amino-5H-dibenzo[a,d]cycloheptene (tropNH(2)) ligand allowed the synthesis of the stable pentacoordinated 18 electron amine olefin rhodium(i) complex [Rh(trop(2)NH)(tropNH(2))]O(3)SCF(3)(); this complex can be cleanly deprotonated [pK(a)(DMSO) = 20.6(1)] to the corresponding amide [Rh(trop(2)N)(tropNH(2))](6) which
Chiral Rhodium(I) and Iridium(I) Amino-Olefin Complexes:? pKa, N-H Bond Dissociation Energy, and Catalytic Transfer Hydrogenation
Maire, P., et al.
Organometallics, 24, 3207-3218 (2005)
Heterolytic splitting of hydrogen with rhodium(I) amides.
Pascal Maire et al.
Angewandte Chemie (International ed. in English), 44(39), 6318-6323 (2005-09-21)
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