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745219

Sigma-Aldrich

(5H-Dibenzo[a,d]cyclohepten-5-yl)diphenylphosphine

≥96.5% (elemental analysis)

Synonym(s):

(5H-Dibenzo[a,d]cyclohepten-5-yl)diphenylphosphane, 5-(Diphenylphosphanyl)dibenzo[a,d]cycloheptene, troppPh

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About This Item

Empirical Formula (Hill Notation):
C27H21P
CAS Number:
210969-23-6
Molecular Weight:
376.43
Beilstein/REAXYS Number:
12068554
MDL number:
MFCD28053534
UNSPSC Code:
12352002
PubChem Substance ID:
329764970
NACRES:
NA.22

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

≤1.0% loss on drying

functional group

phosphine

SMILES string

P(C1=CC=CC=C1)(C2=CC=CC=C2)C3C(C=CC=C4)=C4C=CC5=C3C=CC=C5

InChI

1S/C27H21P/c1-3-13-23(14-4-1)28(24-15-5-2-6-16-24)27-25-17-9-7-11-21(25)19-20-22-12-8-10-18-26(22)27/h1-20,27H

InChI key

KZCMNDBHBVBRLY-UHFFFAOYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ethanol as hydrogen donor: highly efficient transfer hydrogenations with rhodium(I) amides.
Theo Zweifel et al.
Angewandte Chemie (International ed. in English), 47(17), 3245-3249 (2008-03-19)
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
Electromeric rhodium radical complexes.
Florian Frank Puschmann et al.
Angewandte Chemie (International ed. in English), 49(2), 385-389 (2009-12-04)
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)
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)
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