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Butyldi-1-adamantylphosphine

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Butyldi-1-adamantylphosphine Basic information

Product Name:
Butyldi-1-adamantylphosphine
Synonyms:
  • CATACXIUM A
  • BUTYLDI-1-ADAMANTYLPHOSPHINE
  • nbutyl-di(1-adamantyl)phosphine
  • Di(1-adamantyl)-n-butylphosphine
  • Butyldi-1-adamantylphosphine,min.95%[cataCXiumA]
  • BUTYLDI-1-ADAMANTYLPHOSPHINE [CATACXIUM A]
  • cataCXium(R) A
  • Butyldi-1-adamantylphosphine ,95%
CAS:
321921-71-5
MF:
C24H39P
MW:
358.54
EINECS:
691-708-4
Product Categories:
  • Achiral Phosphine
  • Aryl Phosphine
  • organophosphine ligand
Mol File:
321921-71-5.mol
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Butyldi-1-adamantylphosphine Chemical Properties

Melting point:
100°C
Boiling point:
449.6±12.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
color 
white to yellow
Sensitive 
air sensitive
BRN 
8726448
InChI
InChI=1S/C24H39P/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24/h17-22H,2-16H2,1H3
InChIKey
HTJWUNNIRKDDIV-UHFFFAOYSA-N
SMILES
P(CCCC)(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
CAS DataBase Reference
321921-71-5
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29310095
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Butyldi-1-adamantylphosphine Usage And Synthesis

Reaction

  1. Ligand for the Pd-catalyzed Suzuki coupling reaction.
  2. Ligand for the Pd-catalyzed formation of α-aryl ketones.
  3. Ligand for the Pd-catalyzed aminations
  4. Ligand for the Pd-catalyzed Heck reaction.
  5. Ligand used for arylation of benzoic acids.
  6. Ligand for the formylation of aryl bromides.
  7. Ni-catalyzed denitrogenative alkyne insertion reactions of triazoles.
  8. Ligand for palladium-catalyzed aminocarbonylation of aryl halides
  9. Palladium-catalyzed direct arylation of oxazole at C-5 with aryl bromides, chlorides, and triflates
  10. Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides.

Physical properties

Butyldi-1-adamantylphosphine is a white to yellow solid with a melting point of 100°C and an estimated boiling point of 449.6±12.0°C. Store at room temperature, it is air sensitive.

Uses

suzuki reaction

Uses

CataCXium A is a catalyst. CataCXium A is an electron-rich phosphine ligand used for palladium catalyzed cross-coupling reactions like Heck and Suzuki coupling reactions.

Uses

cataCXium A or di-adamantylalkylphosphine is a bulky and electron-rich phosphine ligand that is highly effective for palladium catalyzed cross-coupling reactions such as Heck and Suzuki coupling, Buchwald-Hartwig amination of aryl chlorides, and α-arylation reactions of ketones.

Other applications:

  • palladium-catalyzed carbonylation of aryl and heteroaryl halides
  • palladium-catalyzed synthesis of (hetero)aromatic nitriles
  • palladium-catalyzed aminocarbonylation of aryl halides

General Description

Sold in collaboration with Solvias AG

Synthesis

Phosphonium salt (2.2 mmol) was added to a cooled solution (- 78 ??C) of Et3N (4.44 g, 44 mmol) in di-n-butyl ether (20 mL). The reaction mixture was stirred at -78 ??C for 5 h and then allowed to warm gradually to r.t. The solvent was removed under vacuum and the residue was dissolved in degassed EtOH (5 mL). After stirring for 15 min, the solid was filtered off and dried to yield the desired phosphine, which can be further purified by crystallization from EtOH. Butyldi-1-adamantylphosphine, yield 90%.
31P NMR (C6D6)|?: 24.9. Mp 108-110??C. IR (KBr): 3425 (m, br), 2952 (s), 2847 (s), 2847 (s), 2675 (w), 1446 cm-1 (m). 1H NMR (250 MHz, C6D6): |? = 0.96 (3 H, t, 3JH, H = 7.3 Hz, CH3), 1.35-2.03 (36 H, m, adamantyl-30H, butyl-6H). 13C NMR (62 MHz, C6D6): |? = 41.3 (d, 2JC,P = 11.3 Hz, C-2), 37.4 (C-4), 36.1 (d, 1JC,P = 23.5 Hz, C-1), 33.9 (d, 1JC,P = 26.2 Hz, butyl-|á -CH2), 29.1 (d, 3JC,P = 7.6 Hz, C-3), 24.9 (d, 2JC,P = 13.1 Hz, butyl-|? -CH2), 17.1 (d, 3JC,P = 21.6 Hz, butyl-|? -CH2), 14.3 (butyl-CH3). MS (EI, 70 eV): m/z (%) = 358 (M+, 60), 135 (Ad+, 100).

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