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2-(Dicyclohexylphosphino)biphenyl

Reaction
Product Name
2-(Dicyclohexylphosphino)biphenyl
CAS No.
247940-06-3
Chemical Name
2-(Dicyclohexylphosphino)biphenyl
Synonyms
Cy-John-Phos;(2-biphenyl)dicyclohexylphosphine;CYCLOHEXYL JOHNPHOS;dicyclohexyl-(2-phenylphenyl)phosphane;2-(Dicyclo;98% CyJohnPhos;CyJohnPhos 97%;CyJohnPhos CAS;CAS:247940-06-3;Dicyclohexylphosphino)bipheny
CBNumber
CB8325019
Molecular Formula
C24H31P
Formula Weight
350.48
MOL File
247940-06-3.mol
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2-(Dicyclohexylphosphino)biphenyl Property

Melting point:
102-106 °C(lit.)
Boiling point:
499.5±24.0 °C(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
soluble in Toluene
form 
crystal
color 
white
Sensitive 
Air Sensitive
BRN 
8440533
InChI
InChI=1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2
InChIKey
LCSNDSFWVKMJCT-UHFFFAOYSA-N
SMILES
P(C1=CC=CC=C1C1=CC=CC=C1)(C1CCCCC1)C1CCCCC1
CAS DataBase Reference
247940-06-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38-22
Safety Statements 
36/37/39-26
WGK Germany 
3
F 
10-13-23
TSCA 
No
HazardClass 
AIR SENSITIVE
HS Code 
29310099
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
638099
Product name
CyJohnPhos
Purity
97%
Packaging
1g
Price
$41.3
Updated
2025/07/31
Sigma-Aldrich
Product number
638099
Product name
CyJohnPhos
Purity
97%
Packaging
5g
Price
$133
Updated
2025/07/31
TCI Chemical
Product number
D3388
Product name
2-(Dicyclohexylphosphino)biphenyl
Purity
>98.0%(GC)
Packaging
1g
Price
$39
Updated
2025/07/31
TCI Chemical
Product number
D3388
Product name
2-(Dicyclohexylphosphino)biphenyl
Purity
>98.0%(GC)
Packaging
5g
Price
$140
Updated
2025/07/31
Strem Chemicals
Product number
15-1140
Product name
2-(Dicyclohexylphosphino))-1,1'-biphenyl, 98% CyJohnPhos
Packaging
1g
Price
$31
Updated
2024/03/01
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2-(Dicyclohexylphosphino)biphenyl Chemical Properties,Usage,Production

Reaction

  1. Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
  2. Ligand employed in Suzuki coupling reactions involving aryl chlorides, bromides and triflates.
  3. Useful ligand for the Pd-catalyzed oxidation of alcohols in the presence of chlorobenzenes.
  4. Useful ligand for the Pd-catalyzed amination with ammonia equivalents.
  5. Ligand for the gold(I)-catalyzed intramolecular [4+2] cycloadditions involving 1,3-enynes and arylalkynes with alkenes.
  6. Ligand used in the palladium-catalyzed borylation of aryl bromdies.
  7. Ligand used in the palladium-catalyzed siliylation of aryl chlorides.

Description

2-(Dicyclohexylphosphino)biphenyl is a ligand for the amination of triflates and aryl halides. Optimal ligand for a novel amination reaction (Buchwald reaction)(2) 2-(Dicyclohexylphosphino)biphenyl, a synthetic chemical compound, has found diverse applications in scientific research. Being a cyclic phosphonate derivative of cyclohexanol, this colourless, odourless, and tasteless solid holds a distinct appeal for laboratory use. In scientific research, 2-(Dicyclohexylphosphino)biphenyl has proven invaluable. It serves as an excellent model compound for delving into protein-ligand interactions, thus aiding in studying small molecule effects on protein folding. Moreover, researchers have utilized 2-(Dicyclohexylphosphino)biphenyl to gain insights into protein structures and unravel the mechanism of action behind various drugs. Additionally, the compound has been a vital tool in assessing how environmental factors influence protein structure and function. The interaction between 2-(Dicyclohexylphosphino)biphenyl and proteins primarily occurs through hydrogen bonding and hydrophobic interactions, resulting in high-affinity and specific protein binding. 

Chemical Properties

white to light yellow crystal powde

Uses

Ligand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates.

Uses

suzuki reaction

Uses

2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions.

General Description

CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation
reagent type: ligand
reaction type: Hiyama Coupling
reagent type: ligand
reaction type: Methylations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Oxidations
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

2052-07-5

829-84-5

247940-06-3

General procedure for the synthesis of 2-(dicyclohexylphosphino)biphenyl from 2-bromobiphenyl and dicyclohexylphosphine: under nitrogen protection, a mixture of L1 (0.05 or 0.10 mmol P), [PdCl(η3-C3H5)]2 (0.025 mmol), 2-bromobiphenyl (0.55 mmol) and dicyclohexylphosphine (0.50 mmol) was reacted in a 20 M KOH The mixture in aqueous solution (0.5-1.0 mL) was reacted by shaking at 100 °C for several hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The aqueous filtrate was extracted with degassed toluene (2 mL x 2 times). For the recovered catalyst resin beads, extract with degassed toluene (2 mL x 4 times). All extracts were combined and dried with anhydrous Na2SO4, followed by concentration under vacuum to obtain the crude product. The crude product was purified by silica gel fast chromatography using degassed eluent (n-hexane/Et2O = 10/0-9/1), and the purification process was completed by a YAMAZEN medium-pressure liquid chromatography system, which ultimately yielded the target product 2-(dicyclohexylphosphino)biphenyl.

References

[1] Synlett, 2017, vol. 28, # 20, p. 2966 - 2970

2-(Dicyclohexylphosphino)biphenyl Preparation Products And Raw materials

Raw materials

Bromocyclohexane Nickel(II) chloride hexahydrate Cyclohexane Cinchonidine Diethylamine 2-Bromobiphenyl Bromobenzene Phosphorus trichloride Tetrahydrofuran 1,2-Dibromobenzene Ethyl acetate Copper(I) chloride Dichloromethane Magnesium n-Butyllithium

Preparation Products

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View Lastest Price from 2-(Dicyclohexylphosphino)biphenyl manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
2-(Dicyclohexylphosphino)biphenyl 247940-06-3
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-13
Henan Research New Materials Co., Ltd.
Product
2-(Dicyclohexylphosphino)biphenyl 247940-06-3
Price
US $0.00/Kg
Min. Order
1Kg
Purity
98%; sales036@researchvip.com;18903931628;
Supply Ability
100kg
Release date
2025-04-17
Shanghai UCHEM Inc.
Product
2-(Dicyclohexylphosphino)biphenyl 247940-06-3
Price
US $34.00-582.00/g
Min. Order
25g
Purity
0.98
Supply Ability
25kg
Release date
2023-12-25

247940-06-3, 2-(Dicyclohexylphosphino)biphenylRelated Search:

Tricyclohexyl phosphine Dicyclohexyl phthalate Biphenyl Dicyclohexylcarbodiimide 2-(DICYCLOHEXYLPHOSPHINO)-2'-HYDROXYBIPHENYL 2-(N,N-Dimethylamino)-2-(dicyclohexylphosphino)biphenyl CYCLOHEXYLPHOSPHINE DICYCLOHEXYLPHOSPHINE 2-DICYCLOHEXYLPHOSPHINO-2',6'-DIISOPROPOXYBIPHENYL X-PHOS 2-(Dicyclohexylphosphino)-2'-methylbiphenyl 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl 2-Dicyclohexylphosphino-2μ,4μ,6μ-triisopropylbiphenyl gold(I) bis(trifluoromethanesulfonyl)imide 2,2'-BIS(DICYCLOHEXYLPHOSPHINO)BIPHENYL 2'-DICYCLOHEXYLPHOSPHINO-2,6-DIMETHOXY-3-SULFONATO-1,1'-BIPHENYL HYDRATE SODIUM SALT (R)-(+)-2,2'-BIS(DICYCLOHEXYLPHOSPHINO)-1,1'-BINAPHTHYL 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO& 2-(Dicyclohexylphosphino)-2'-isopropylbiphenyl

  • CYCLOHEXYL JOHNPHOS
  • 2-(DICYLOHEXYLPHOSPHINO)BIPHENYL
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  • (2-BIPHENYLYL)DICYCLOHEXYLPHOSPHINE
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  • PHOSPHINE, [1,1''-BIPHENYL]-2-YLDICYCLOHEXYL-
  • 2-(Dicyclohexylphosphino))-1,1'-biphenyl, 98% CyJohnPhos
  • 2-(Dicyclohexyl)phosphine biphenyl
  • 2-(Dicyclo
  • 2-(Dicyclohexylphosphino)biphenyl, Cyclohexyl JohnPhos
  • 2-(Dicyclohexylphosphino)biphenyl ,95%
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  • 2-(Dicyclohexylphosphino)biphenyl, 98% 500MG
  • biphenyl-2-yldicyclohexylphosphine
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  • 98% CyJohnPhos
  • 2-dicyclohexylphosphino-1,1'-biphenyl
  • [1,1'-Biphenyl]-2-yldicyclohexylphosphine
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  • CyJohnPhos 97%
  • 2-(Dicyclohexylphosphino)biphenyl&gt
  • High purity CAS 247940-06-3 2-(Dicyclohexylphosphino)biphenyl in stock
  • CyJohnPhos CAS
  • 2-(Dicyclohexylphosphino))-1,1'-biphenyl, 98%
  • Phosphine, [1,1'-biphenyl]-2-yldicyclohexyl-
  • CAS:247940-06-3
  • 247940-06-3
  • C12H9PC6H112
  • C24H31P
  • Phosphorus Compounds
  • Catalysis and Inorganic Chemistry
  • Buchwald Ligands
  • Phosphine Ligands
  • Synthetic Organic Chemistry
  • organophosphine ligand
  • Ligand
  • Achiral Phosphine
  • Aryl Phosphine
  • Buchwald Ligands Series
  • Buchwald Ligands&Precatalysts
  • Phosphines