Reaction
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X-PHOS

Reaction
Product Name
X-PHOS
CAS No.
564483-18-7
Chemical Name
X-PHOS
Synonyms
5-BROMO-4-CHLORO-3-INDOLYL PHOSPHATE;2-Dicyclohexylphosphino-2;dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphane;X-PH0S;dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;X-PHOS;98% XPhos;2-(DicycL;XPhos 97%;XPhos, >=98%
CBNumber
CB3357527
Molecular Formula
C33H49P
Formula Weight
476.72
MOL File
564483-18-7.mol
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X-PHOS Property

Melting point:
187-190 °C(lit.)
Boiling point:
569.8±50.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Benzene (Slightly)
form 
Powder
color 
white
Sensitive 
Air Sensitive
Stability:
Air Sensitive
InChIKey
UGOMMVLRQDMAQQ-UHFFFAOYSA-N
SMILES
P(C1CCCCC1)(C1CCCCC1)C1=CC=CC=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
CAS DataBase Reference
564483-18-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38-22-40
Safety Statements 
37/39-26-36/37
WGK Germany 
3
TSCA 
No
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H351Suspected of causing cancer

Precautionary statements

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
638064
Product name
XPhos
Purity
97%
Packaging
1g
Price
$95.4
Updated
2025/07/31
Sigma-Aldrich
Product number
638064
Product name
XPhos
Purity
97%
Packaging
5g
Price
$176
Updated
2025/07/31
TCI Chemical
Product number
D5038
Product name
2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl
Purity
>98.0%(GC)
Packaging
1g
Price
$98
Updated
2025/07/31
TCI Chemical
Product number
D5038
Product name
2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl
Purity
>98.0%(GC)
Packaging
5g
Price
$288
Updated
2025/07/31
Strem Chemicals
Product number
15-1149
Product name
2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl, min. 98% XPhos
Packaging
500mg
Price
$33
Updated
2024/03/01
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X-PHOS Chemical Properties,Usage,Production

Reaction

  1.  Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates.
  2.  Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling reaction and carbonyl enolate coupling.
  3.  Ligand used for the chemoselective amination of aryl chlorides.
  4.  Ligand used for the Pd-catalyzed borylation of aryl chlorides, for the formation of trifluoroborates.
  5.  Ligand used for the Pd-catalyzed amination of vinyl halides and triflates.
  6.  Ligand used for the Pd-catalyzed three-component synthesis of indoles.
  7.  Ligand used for the Pt-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes.
  8.  Ligand used for the Pd-catalyzed synthesis of carbazoles.
  9.  Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling of aryl chloride and NHC-boranes.
  10.  Ligand used for the direct arylation of picoline N-oxide.
  11.  Ligand used for the Negishi coupling of 2-heterocyclic organozinc reagents.
  12.  Catalyst for a phosphine-catalyzed Heine reaction.
  13.  Ligand used for the palladium-catalyzed oxidative coupling of indoles and heteroarenes.
  14.  Ligand used for the silver-catalyzed hydrogenation of aldehydes.
  15.  Ligand used for the palladium-catalyzed cyanation of heterycyclic halides.



Chemical Properties

White crystalline powder

Uses

suzuki reaction

Uses

Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates. XPHOS is used as a regent in the synthesis of novel [1,2,4]triazolo[4,3-a]pyrazine derivatives as potential selective c-met inhibitors with improved pharmacokinetic properties.

General Description

This product has been enhanced for catalytic efficiency.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

Synthesis

21524-34-5

16523-54-9

583-53-9

564483-18-7

Under nitrogen protection, 200 mL of tetrahydrofuran (THF) and 31 g of 2-bromo-1,3,5-triisopropylbenzene were added to a 1 L three-necked flask. The reaction mixture was cooled to 0 °C and 46 mL of a 2.5 M hexane solution of n-butyllithium was slowly added dropwise. After the dropwise addition was completed, the reaction continued to be stirred at 0 °C for 1 hour. Subsequently, 24.6 g of 1,2-dibromobenzene was slowly added dropwise at the same temperature. After completion of the dropwise addition, the reaction was continued at 0°C for 1 hour. Next, 42 mL of 2.5 M hexane solution of n-butyllithium was added dropwise to the reaction mixture at 0 °C. After the dropwise addition was completed, the reaction was continued with stirring at 0 °C for 1 hour. Then, 26.7 g of dicyclohexylphosphonium chloride was slowly added dropwise and the reaction mixture was allowed to warm up to room temperature naturally and the reaction was continued to be stirred for 2 hours. Upon completion of the reaction, 200 mL of saturated aqueous ammonium chloride solution was slowly added dropwise to quench the reaction under the cooling of an ice bath. After performing phase separation, the organic phase was concentrated and crystallized by adding methanol. The solid was collected by filtration to afford 44.5 g of a white crystalline product of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl in 89% yield.

References

[1] Patent: CN105273006, 2016, A. Location in patent: Paragraph 0069; 0070

X-PHOS Preparation Products And Raw materials

Raw materials

2-Bromochlorobenzene Dicyclohexylchlorophosphine Carbon tetrachloride Hydroquinone Tetrahydrofuran 1,3,5-Triisopropylbenzene Ethyl acetate Copper(I) chloride Bromine Dichloromethane Methanol Iron Magnesium

Preparation Products

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X-PHOS Suppliers

Americas 1 Belgium 3 Canada 2 China 413 Europe 1 France 3 Germany 9 India 15 Ireland 1 Italy 1 Japan 2 Norway 1 Russia 1 South Korea 1 Switzerland 2 The Netherlands 1 Ukraine 1 United Kingdom 10 United States 42 Global 510
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732-484-9848
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888-484-5008
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sales@chemscene.com
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+1-858-6993322
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(+1)-858-876-1948
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View Lastest Price from X-PHOS manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
X-PHOS 564483-18-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-04
Speranza Chemical Co., Ltd.
Product
2-(DICYCLOHEXYLPHOSPHINO)-2',4',6'-TRI-I-PROPYL-1,1'-BIPHENYL 564483-18-7
Price
US $0.00-0.00/KG
Min. Order
5KG
Purity
98%
Supply Ability
25KG
Release date
2024-11-05
Hebei Zhuanglai Chemical Trading Co Ltd
Product
X-PHOS 564483-18-7
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-12-17

564483-18-7, X-PHOSRelated Search:

5-BROMO-4-CHLORO-3-INDOLYL PHOSPHATE DIPOTASSIUM SALT 2-(Dicyclohexylphosphino)biphenyl DI-N-PENTYLPHENYLPHOSPHINE DIBUTYLPHENYLPHOSPHINE 2-(Dicyclohexylphosphino)-2'-methylbiphenyl X-PHOS Dicyclohexylphenylphosphine 5-BROMO-4-CHLORO-3-INDOLYL PHOSPHATE DISODIUM SALT PNP-PHOS K PNP-PHOS 2 CHX PNP-PHOS DINA HEXAHYDRATE 5-Bromo-4-chloro-3-indolyl phosphate hydrate disodium salt PHOS-ALPHA-D-GLC 2H2O 5-Bromo-4-chloro-3-indolyl phosphate p-toluidine salt PNP-PHOS DINA CYCLOHEXYLPHOSPHINE DICYCLOHEXYLPHOSPHINE GOAT F(AB')2 ANTI-HUMAN LAMBDA (F+B) ALK PHOS

  • X-PHOS
  • 5-BROMO-4-CHLORO-3-INDOLYL PHOSPHATE
  • 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO-PROPYL-1,1'-BIPHENYL
  • 2-Dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, X-PHOS
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl,min.98%X-Phos
  • -biphenyl]-2-yl]phosphane
  • (2-(2,4,6-triisopropylphenethyl)phenyl)dicyclohexylphosphine(X-Phos)
  • X-PH0S
  • 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 98+%
  • ChemDose(R), X-Phos impregnated tablets, 2-Dicyclohexylphosphino-2μ,4μ,6μ-triisopropylbiphenyl impregnated tablets
  • X-Phos, ChemDose(R) tablets
  • 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbip
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,
  • 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl ,97%
  • 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl,XPhos
  • 2-Dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, 98+% X-PHOS
  • 98% XPhos
  • 2-(DicyclohexylphosphiNA)-2',4',6'-triisopropylbiphenyl
  • 2,,4',6'-Diisopropyl-1,1'-biphenyl-2-yldicyclohexylphosphine
  • 2-(Dicyclohexylphosphino)-2',4
  • 2-(Dicyclohexylphosphanyl)-2',4',6'-tris(isopropyl)biphenyl
  • Dicyclohexyl[2',4',6'-tris(prop-2-yl)biphenyl-2-yl]phosphine, Dicyclohexyl[2',4',6'-tris(prop-2-yl)biphenyl-2-yl]phosphane, X-phos
  • 2-(DicycL
  • phosphino)-2',4',6'-tri-i-propyL
  • Dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine
  • Phosphine, dicyclohexyl[2',4',6'-tris(1-Methylethyl)[1,1'-biphenyl]-2-yl]-
  • XPhos 97%
  • 2-Dicyclohexylphosphino-2
  • 2-(DICYCLOHEXYLPHOSPHINO)-2',4',6'-TRI-I-PROPYL-1,1'-BIPHENYL OR X-PHOS
  • (2-(2,4,6-triisopropylphenethyl)phenyl)dicyclohexylphosphine
  • X-PHOS,2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl
  • XPhos, >=98%
  • Dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane
  • X-Phos, ChemDose? tablets
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl, min. 98%
  • dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphane
  • dicyclohexyl[2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphane
  • 2-Dicyclohexylphosphino-2',4',6'-t
  • dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane
  • [2'-(methylamino)-[1,1'-biphenyl]-2-yl]palladio methanesulfonate
  • X-Phos, ChemDose(TM) tablets
  • -1,1'-biphenyL
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl,min.98%
  • X-Phos ( 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl)
  • 2-Dicyclohexylphosphino-2',4',6'-trisopropyl-1,1'-biphenyl(X-phos)
  • 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO-PROPYL-1,1'-BIPHENYL,xphos
  • X-Phos (2-Dicyclohexylphosphino-2,4,6-Triisopropylbiphenyl) extrapure, 98%
  • 2-Dicyclohexylphosphate-2 ', 4', 6 '- triisopropylbiphenyl
  • 2-dicyclohexylphosphine 2',4',6' -triisopropyl biphenyl
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl
  • XPhos(2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl)
  • 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl
  • dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine
  • (2-Methylallyl)palladiumchloride dimer
  • 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl (Xphos)
  • Abemaciclib Impurity 31
  • Abemaciclib Impurity 39
  • Phosphine,dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]-