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321921-71-5

321921-71-5 Structure

321921-71-5 Structure
IdentificationBack Directory
[Name]

Butyldi-1-adamantylphosphine
[CAS]

321921-71-5
[Synonyms]

CATACXIUM A
cataCXium(R) A
Catalyst 1 ,95%
cataCXium(R) A 95%
Di(adamantan-1-yl)
BUTYLDI-1-ADAMANTYLPHOSPHINE
nbutyl-di(1-adamantyl)phosphine
Di(1-adamantyl)-n-butylphosphine
Bis(1-adaMantyl)-butyl-phosphane
Bis(adamant-1-yl)(butyl)phosphine
Bis(1-AdaMantyl)-n-Butylphosphine
Butyldi-1-adamantylphosphine ,95%
Di(adaMantan-1-yl)(butyl)phosphine
bis(adaMantan-1-yl)(butyl)phosphane
Di(1-adamantyl)-n-butylphosphine,95%
Di(1-adamantyl)-n-butylphosphine 95%
Butyldi-1-adamantylphosphine,min. 95%
BUTYLDI-1-ADAMANTYLPHOSPHINE [CATACXIUM A]
Butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine
Butyldi-1-adamantylphosphine,min.95%[cataCXiumA]
Phosphine,butylbis(tricyclo[3.3.1.13,7]dec-1-yl)-
Butyldi-1-adamantylphosphine, min. 95% [cataCXium(R) A]
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C24H39P
[MDL Number]

MFCD05861606
[MOL File]

321921-71-5.mol
[Molecular Weight]

358.54
Chemical PropertiesBack Directory
[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
Hazard InformationBack Directory
[Uses]

suzuki reaction
[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.
[General Description]

Sold in collaboration with Solvias AG
[reaction suitability]

reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Cross Couplings
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
[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).Synthesis_321921-71-5
[References]

[1] Patent: US2004/68131, 2004, A1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P271-P280
[Safety Statements ]

24/25
[WGK Germany ]

3
[HS Code ]

29310095
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Hydrochloric acid-->Ethyl acetate-->Tetrahydrofuran-->Chloroform-->Sodium sulfate-->Triethylamine-->Lithium Aluminum Hydride-->Nitrogen-->Aluminum chloride-->Phosphorus trichloride-->Dibutyl ether-->Clindamycin palmitate hydrochloride-->Adamantane-->1-Iodobutane
Questions And AnswerBack Directory
[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
Spectrum DetailBack Directory
[Spectrum Detail]

Butyldi-1-adamantylphosphine(321921-71-5)FT-IR
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