Basic information Uses Reactions Safety Supplier Related
ChemicalBook >  Product Catalog >  Organic Chemistry >  Phosphines >  2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Basic information Uses Reactions Safety Supplier Related

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Basic information

Product Name:
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
Synonyms:
  • 98% SPhos
  • 2-Dicyclohexylphosphino-2',6'-diMethoxy-1,1'-biphenyl ,98%
  • 2-Dicyclohexylphosphino-2', 6-diMethoxybihenyl
  • 2-DicyclohexylphosphiNA-2',6'-diMethoxybiphenyl
  • SPhos 97%
  • 2-Dicyclohexylphosphino-2',6'-diMethoxybiphenyl, 6'-diMethoxybiphenyl
  • 2 - dicyclohexyl phosphine - 2 ', 6 '- diMethoxy - 1, 1' - two PCB
  • 2-Dicyclohexylphosphino-2',6'-
CAS:
657408-07-6
MF:
C26H35O2P
MW:
410.53
EINECS:
613-838-2
Product Categories:
  • Phosphines
  • Achiral Phosphine
  • Aryl Phosphine
  • Buchwald Ligands Series
  • Buchwald Ligands&Precatalysts
  • bc0001
Mol File:
657408-07-6.mol
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2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Chemical Properties

Melting point:
164-166°C
Boiling point:
513.3±40.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
soluble in Chloroform
form 
crystal
color 
white
Sensitive 
Air Sensitive
InChI
InChI=1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3
InChIKey
VNFWTIYUKDMAOP-UHFFFAOYSA-N
SMILES
P(C1CCCCC1)(C1CCCCC1)C1=CC=CC=C1C1=C(OC)C=CC=C1OC
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Safety Information

Hazard Codes 
Xn
Risk Statements 
40
Safety Statements 
24/25-36/37
WGK Germany 
3
TSCA 
No
HS Code 
2931499090
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2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Usage And Synthesis

Uses

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] 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. 
SPhos may be used as a ligand in the following processes:
• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.• Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.• Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

Reactions

  1. Ligand/palladium catalyst for general Suzuki-Miyaura cross-coupling reactions.
  2. Ligand/palladium catalyst for the Suzuki-Miyaura coupling of aryltrifluoroborates with aryl chlorides.
  3. Ligand/palladium catalyst for the Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.
  4. Ligand/palladium catalyst for the Kumada-Corriu cross-coupling reaction.
  5. Ligand/palladium catalyst for the borylation of aryl halides with pinacol borane.
  6. Suzuki couplings involving amino acids. Synthesis of biaryl derivatives of 4-hydroxyphenyl glycine, tyrosine and tryptophan.
  7. Synthesis of substituted adamantylzinc reagents using Mg-insertion in the presence of zinc chloride.
  8. Highly efficient catalyst for the palladium-catalyzed Suzuki-Miyura reaction of heteroaryl halides and heteroaryl boronic acids
  9. and esters.

Chemical Properties

White solid

Uses

S-Phos is a catalyst that is used in the preparation of thiadiazoles as DGAT1 inhibitors with potential in metabolic diseases treatment.

Uses

suzuki reaction

General Description

SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] 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: catalyst
reaction type: Cross Couplings

Synthesis

694-80-4

151-10-0

16523-54-9

657408-07-6

To a solution of 1,3-dimethoxybenzene (2 mL, 15.30 mmol) in anhydrous THF (35 mL) was slowly added n-butyllithium (nBuLi, 6.2 mL, 15.50 mmol) through a dropping funnel over 5 min at 0 °C. The reaction mixture was stirred at room temperature for 3.5 h. After stirring, 2-bromochlorobenzene (1.6 mL, 13.70 mmol) was added slowly dropwise through a syringe at 0 °C for 30 min. After stirring for 15 min, the reaction mixture was cooled to -78 °C and n-butyllithium (6.20 mL, 15.50 mmol) was again added slowly through a dropping funnel over 5 min. 30 min later, chlorodicyclohexylphosphine (3.03 mL, 13.70 mmol) was added. The reaction mixture was kept at -78 °C for 1 h, during which rapid mechanical stirring was performed. Subsequently, the reaction mixture was warmed to room temperature and the resulting precipitate was filtered through a silica gel sintered disc covered with a cellulose acetate layer and washed with 600 mL of ethyl acetate. The filtrate was concentrated by rotary evaporation and the resulting orange oil was recrystallized in acetone to give white crystalline S-Phos ligand in 36% yield (1.22 g, 2.97 mmol). Melting point: 163-165 °C (literature value 162.0-162.5 °C); Thin layer chromatography (TLC) conditions: ethyl acetate/cyclohexane (10/90), Rf = 0.65; 1H-NMR (CDCl3): δ = 0.99-1.26 (m, 10H, H(Cy)), 1.60-1.77 (m, 12H, H(Cy)), and 3.67 (s, 6H, Me), 6.58 (d, 2H, J = 8.2 Hz, H3' and H5'), 7.15-7.18 (m, 1H, H(Ar)), 7.18-7.42 (m, 3H, H(Ar)), 7.57 (d, 1H, J = 7.4 Hz, H(Ar)) ppm; 13C-NMR (CDCl3): δ = 26.5, 27.3, 27.4, 27.6, 29.0, 29.1, 29.8, 30.1, 33.8, 34.0 (C(Cy)), 55.3 (Cb), 103.1 (Ca), 126.2, 128.2, 128.8 (C3', C4', C5'), 130.9, 131.00, 132.4. 135.8 (C3, C4, C5, C6), 135.8, 136.1, 142.7, 143.1, 157.4 (C2', C6') ppm; IR (KBr): υ = 3000, 2923, 2851, 1588, 1471, 1442, 1428, 1108 cm-1.

References

[1] Patent: US2011/184059, 2011, A1. Location in patent: Page/Page column 9

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Preparation Products And Raw materials

Raw materials

Ethyl acetateTetrahydrofuranPETROLEUM ETHERn-ButyllithiumMagnesium1,3-Dimethoxybenzene1,2-DibromobenzeneDicyclohexylchlorophosphine

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylSupplier

Sinocompound Catalysts Co., Ltd. Gold
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Aikon International Limited Gold
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2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl(657408-07-6)Related Product Information