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759171

Sigma-Aldrich

CPhos

98%

Synonym(s):

2-Dicyclohexylphosphino-2′,6′-bis(N,N-dimethylamino)biphenyl

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About This Item

Empirical Formula (Hill Notation):
C28H41N2P
CAS Number:
1160556-64-8
Molecular Weight:
436.61
MDL number:
MFCD27978504
UNSPSC Code:
12352116
PubChem Substance ID:
329766759
NACRES:
NA.22

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Quality Level

100

Assay

98%

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

108-113 °C

functional group

phosphine

SMILES string

CN(C)C(C=CC=C1N(C)C)=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4

InChI

1S/C28H41N2P/c1-29(2)25-19-13-20-26(30(3)4)28(25)24-18-11-12-21-27(24)31(22-14-7-5-8-15-22)23-16-9-6-10-17-23/h11-13,18-23H,5-10,14-17H2,1-4H3

InChI key

DRNAQRXLOSUHBQ-UHFFFAOYSA-N

Application

CPhos can be used:
  • As a ligand in the Pd-catalyzed synthesis of 3-cyclopentylindole derivatives,[1] dihydrobenzofurans[2] and trans-bicyclic sulfamides.[3]
  • To synthesize palladacycle precatalysts for Negishi coupling of secondary alkylzinc.[4][5][6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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
SHBQ8323
SHBJ1746
SHBH0943V
SHBG7123V
SHBF9365V

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Palladium-Catalyzed Negishi Coupling of ?-CF3 Oxiranyl Zincate: Access to Chiral CF3-Substituted Benzylic Tertiary Alcohols.
Zhang H and Buchwald SL
Journal of the American Chemical Society, 139(33), 11590-11594 (2017)
Synthesis of 2, 3-dihydrobenzofurans via the palladium catalyzed carboalkoxylation of 2-allylphenols.
Hutt JT and Wolfe JP
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 3(10), 1314-1318 (2016)
Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.
Han C and Buchwald SL
Journal of the American Chemical Society, 131(22), 7532-7533 (2009)
Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.
Kirsch JK, et al.
The Journal of Organic Chemistry, 83(21), 13568-13573 (2018)
Stereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1, 3-Asymmetric Induction by Manipulating Mechanistic Pathways.
Babij NR, et al.
Organic Letters, 16(12), 3412-3415 (2014)
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