Butyldi-1-adamantylphosphine

Butyldi-1-adamantylphosphine Basic information
Reaction
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
Butyldi-1-adamantylphosphine Structure
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
InChIInChI=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
InChIKeyHTJWUNNIRKDDIV-UHFFFAOYSA-N
SMILESP(CCCC)(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2
CAS DataBase Reference321921-71-5
Safety Information
Safety Statements 24/25
WGK Germany 3
HS Code 29310095
MSDS Information
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.
Reactions of 321921-71-5_1
Reactions of 321921-71-5_2
Physical propertiesButyldi-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.
Usessuzuki reaction
UsesCataCXium 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.
UsescataCXium 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 DescriptionSold in collaboration with Solvias AG
SynthesisPhosphonium 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).Synthesis_321921-71-5
CERIUM(III) CHLORIDE Di(1-adaMantyl)chlorophosphine Diphenyl-2-pyridylphosphine Di(1-adamantyl)-n-butylphosphine hydriodide Butylmagnesium chloride Adamantane N-BUTYLMAGNESIUM BROMIDE DI-N-BUTYLMAGNESIUM DI-1-ADAMANTYLPHOSPHINE DI-I-PROPYLPHOSPHINE Urea n-Butylboronic acid Oxalyl chloride BENZYLDI-1-ADAMANTYLPHOSPHINE Glycolic acid Butyldi-1-adamantylphosphine CYCLOHEXYLDI(1-ADAMANTYL)PHOSPHINE Phosphine

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.