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455164

Sigma-Aldrich

Tricyclohexylphosphine solution

20 wt. % in toluene

Synonym(s):

NSC 158657, PCy3

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About This Item

Linear Formula:
(C6H11)3P
CAS Number:
2622-14-2
Molecular Weight:
280.43
Beilstein:
957171
MDL number:
MFCD00003853
UNSPSC Code:
12350000
PubChem Substance ID:
24869033
NACRES:
NA.22

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

concentration

20 wt. % in toluene

functional group

phosphine

SMILES string

C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

InChI

1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2

InChI key

WLPUWLXVBWGYMZ-UHFFFAOYSA-N

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Application

Catalyst for:
  • Carbonylative Suzuki-coupling of benzyl halides with potassium aryltrifluoroborates
  • Suzuki-Miyaura reactions of aryl sulfonates / halides with arylboronic acids
  • Synthesis of an acromelic acid A analog based 11C-labeled PET tracer
  • Synthesis of (-)-Exiguolide and its analogues
  • Allylation of zinc enolates
Reagent used as a ligand for a range of metal-catalyzed organic transformations.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

51.8 °F - closed cup

Flash Point(C)

11 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

455164-BULK:
455164-500G:4548173153735
455164-VAR:
455164-100G:4548173153728

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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Adrian Tlahuext-Aca et al.
Dalton transactions (Cambridge, England : 2003), 43(42), 15997-16005 (2014-09-19)
Ni(0)-catalyzed dehydrogenation of benzylic-type imines was performed to yield asymmetrical tetra-substituted imidazoles and 2-imidazolines. This was achieved with a single operational step while maintaining good selectivity and atom economy. The catalytic system shows low to moderate tolerance for fluoro-, trifluoromethyl-
Sebastijan Kovačič et al.
Macromolecular rapid communications, 36(17), 1605-1611 (2015-07-15)
Metal-organic frameworks (MOFs) nanoparticles in combination with a nonionic surfactant (Pluronic L-121) are used to stabilize dicyclopentadiene (DCPD)-in-water high internal phase emulsions (HIPEs). The resulting HIPEs containing the MIL-100(Fe) nanoparticles (MIL: Materials of Institut Lavoisier) at the interface between the

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