ChemicalBook--->CAS DataBase List--->564483-19-8

564483-19-8

564483-19-8 Structure

564483-19-8 Structure
IdentificationBack Directory
[Name]

2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL
[CAS]

564483-19-8
[Synonyms]

2&lsquo
tBuXPhos
t-Bu XPhos
tBuXPhos 97%
98% tBuXPhos
di-t-Bu-XPhos
t-butyl-Xphos
TERT-BUTYL X-PHOS
2-Di-t-butylphosphino-2',4',6'
-DI-Tert-Butylphosphino-2,4,6-Triisopropylbiphenyl
2-di-tert-butylphosphino-2',4',6'-triisopropylbiph
2-Di-tert-butylphosphino-2',4',6'-trisopropylbinphenyl
2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL
2-DI-T-BUTYLPHOSPHINO-2',4',6'-TRI-I-PROPYL-1,1'-BIPHENYL
2-Di-t-butylphosphiNA-2',4',6'-tri-i-propyl-1,1'-biphenyl
Di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine
2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl ,98%
2-DI-TERT-BUTYLPHOSPHINO-2',4', 6'-TRI-I-PROPYL-1,1'-BIPHENYL
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl,min.98%
Di-tert-butyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl,98% tBuXPhos
2-DI-T-BUTYLPHOSPHINO-2'',4'',6''-TRI-I-PROPYL-1,1''-BIPHENYL, MIN. 98%
2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl,tert-Butyl XPhos
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, t-butylXPhos
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl,min.98%t-butylXPhos
2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, Min. 98% t-Bu-X-PHOS
Bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine
phosphine, bis(1,1-diMethylethyl)[2',4',6'-tris(1-Methylethyl)[1,1'-biphenyl]-2-yl]-
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C29H45P
[MDL Number]

MFCD06411306
[MOL File]

564483-19-8.mol
[Molecular Weight]

424.64
Questions And AnswerBack Directory
[Uses]

tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.
tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.
It can be used in the following reactions:
• Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
• Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
• Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.
[Reactions]

  • Effective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles and amino heterocycles.
  • Ligand used in the Pd-catalyzed synthesis of phenols from aryl halides and KOH.
  • Ligand used in the Pd-catalyzed of benzoic acids from aryl halides and CO2.
  • Ligand used in the Pd-catalyzed trifluoromethylation of vinyl sulfonates.
  • Ligand used in the Pd-catalyzed arylation of nitroacetates.
  • Ligand used in the Pd-catalyzed Suzuki−Miyaura cross-coupling of allylboronates and aryl halides.
  • Ligand used in the Pd-catalyzed cyanation of (hetero)arylchlorides and bromides.
  • Ligand used in the Pd-catalyzed C–N cross coupling of sulfinamides and aryl halides.
  • Ligand used in the Pd-catalyzed arylation of cyanamides. 
Reactions of 564483-19-8_1 Reactions of 564483-19-8_2  
Chemical PropertiesBack Directory
[Melting point ]

148-151 °C(lit.)
[Boiling point ]

493.5±45.0 °C(Predicted)
[storage temp. ]

2-8°C, protect from light, stored under nitrogen
[solubility ]

soluble in Toluene
[form ]

Crystalline Powder
[color ]

White
[InChI]

InChI=1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3
[InChIKey]

SACNIGZYDTUHKB-UHFFFAOYSA-N
[SMILES]

P(C(C)(C)C)(C(C)(C)C)C1=CC=CC=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
Hazard InformationBack Directory
[Chemical Properties]

White to pale yellow
[Uses]

Effective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles and amino heterocycles
[Uses]

suzuki reaction
[General Description]

tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
[reaction suitability]

reagent type: ligand
[Synthesis]

Di-tert-butylchlorophosphane

13716-10-4

2-Bromochlorobenzene

694-80-4

1-BROMO-2,4,6-TRIISOPROPYLBENZENE

21524-34-5

2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL

564483-19-8

1. In a 1L three-necked flask, 32.5 g of 2-bromo-1,3,5-triisopropylbenzene, 5.6 g of magnesium shavings, and 300 mL of anhydrous tetrahydrofuran (THF) were added to prepare a Grignard reagent. 2. Under stirring, 20 g of 2-bromochlorobenzene was slowly added dropwise to the above solution to form 2,4,6-triisopropyl-2'-bromodiphenyl Grignard reagent, and the reaction was refluxed for 2 hours. 3. After completion of the reaction, cooled to room temperature, 2.4 g of tetrakis(triphenylphosphine)palladium was added as a catalyst and stirred for 30 minutes. 4. At room temperature, 18.8 g of di-tert-butylphosphonium chloride was slowly added dropwise to the reaction mixture and the reaction was continued at reflux for 5 hours. 5. The reaction mixture was cooled in an ice water bath and 200 mL of saturated aqueous ammonium chloride solution was slowly added dropwise to quench the reaction. 6. The organic phase was separated and crystallized by addition of methanol and filtered to afford 41.7 g of the white solid product 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl in 94% yield.

[References]

[1] Patent: CN105859774, 2016, A. Location in patent: Paragraph 0078; 0079; 0080; 0081
[2] Journal of the American Chemical Society, 2003, vol. 125, # 22, p. 6653 - 6655
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280-P305+P351+P338-P304+P340-P405-P501A
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37/39
[WGK Germany ]

3
[TSCA ]

No
[HS Code ]

29310099
[Storage Class]

11 - Combustible Solids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Bromine-->Benzene-->Aluminum chloride-->Carbon tetrachloride-->Iron-->Magnesium-->Phosphorus trichloride-->Copper(I) chloride-->1,2-Dibromoethane-->2-Bromopropane-->2-Chloro-2-methylpropane-->1,2-Dibromobenzene
[Preparation Products]

1-Butanone, 1-(4-fluorophenyl)-4-[(6bS,10aR)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]--->tBuXPhos-Pd-G3
Spectrum DetailBack Directory
[Spectrum Detail]

2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL(564483-19-8)1HNMR
2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL(564483-19-8)31PNMR
2-DI-TERT-BUTYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL(564483-19-8)FT-IR
564483-19-8 suppliers list
Company Name: Sinocompound Catalysts Co., Ltd.  Gold
Telephone: 0512-67216630 67216634
Website: http://www.sinocompound.com
Company Name: Xinxiang Runyu Material Co., Ltd.  Gold
Telephone: 166-166-37336996 15690792173
Website: www.runvmat.com/
Company Name: Puyang Huicheng Electronic Material Co. Ltd.  Gold
Telephone: 0393-8910800 18339358320
Website: www.huichengchem.com/
Company Name: Zhengzhou Kingorgchem Chemical Technology Co., Ltd.gy Co., Ltd.  Gold
Telephone: 0371-65511006 18625597674
Website: http://www.kingorgchem.com/
Company Name: BeiJing Greenchem Technology Co.,Ltd.  Gold
Telephone: 131-21959385 18804271668
Website: http://www.bjgreenchem.com/index.html
Company Name: Henan Research New Material Co., Ltd.  Gold
Telephone: 86-18903931531 18903931628
Website: www.researchvip.com
Company Name: J & K SCIENTIFIC LTD.  
Telephone: 18210857532 18210857532
Website: https://www.jkchemical.com
Company Name: Meryer (Shanghai) Chemical Technology Co., Ltd.  
Telephone: 4006356688 18621169109
Website: www.x-labseek.com/
Company Name: Alfa Aesar  
Telephone: 400-6106006
Website: http://chemicals.thermofisher.cn
Company Name: ShangHai DEMO Chemical Co.,Ltd  
Telephone: 400-021-7337 2355568890
Website: www.demochem.com
Company Name: Beijing HwrkChemical Technology Co., Ltd  
Telephone: 89508211 18501085097
Website: www.hwrkchemical.com
Company Name: Energy Chemical  
Telephone: 400-0056266
Website: www.energy-chemical.com
Company Name: Beijing Ouhe Technology Co., Ltd  
Telephone: 13552068683 13522913783
Website: www.ouhetech.cn/
Company Name: JinYan Chemicals(ShangHai) Co.,Ltd.  
Telephone: 13817811078
Website: www.jingyan-chemical.com
Company Name: Jia Xing Isenchem Co.,Ltd  
Telephone: 0573-85285100 18627885956
Website: https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm
Company Name: Beijing VSciChem Technology Co., Ltd.  
Telephone: 13811761079
Website: http://www.vscichem.com
Company Name: Accela ChemBio Co.,Ltd.  
Telephone: 021-50795510 4000665055
Website: http://www.shao-yuan.com/
Company Name: Shanghai Longsheng chemical Co.,Ltd.  
Telephone: 58099637 13585536065
Website: www.shlshg.com
Tags:564483-19-8 Related Product Information
787618-22-8 657408-07-6 1160556-64-8 251320-86-2 247940-06-3 1160556-61-5 213697-53-1 255835-82-6 1070663-78-3 564483-18-7 131274-22-1 224311-51-7