Butyldi-1-adamantylphosphine

Base Information

• Chemical Name: Butyldi-1-adamantylphosphine
• CAS No.: 321921-71-5
• Molecular Formula: C24H39P
• Molecular Weight: 358.547
• Hs Code.: 29310095
• Mol file: 321921-71-5.mol

Synonyms:Bis(adamant-1-yl)(butyl)phosphine;Bis(adamantan-1-yl)(butyl)phosphine;Butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine;Butyldi(1-adamantanyl)phosphine;CataCXium A;Di-1-adamantylbutylphosphine;Diadamantyl-n-butylphosphane;

Chemical Property of Butyldi-1-adamantylphosphine

Chemical Property:

• Vapor Pressure: 7.51E-08mmHg at 25°C
• Melting Point: 100 °C
• Boiling Point: 449.6 °C at 760 mmHg
• Flash Point: 239 °C
• PSA: 13.59000
• LogP: 7.20600
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: air sensitive

Purity/Quality:

98% ^*data from raw suppliers

Butyldi-1-adamantylphosphine, min. 95% [cataCXium(R) A] ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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 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. 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 halidespalladium-catalyzed synthesis of (hetero)aromatic nitrilespalladium-catalyzed aminocarbonylation of aryl halides

Technology Process of Butyldi-1-adamantylphosphine

There total 10 articles about Butyldi-1-adamantylphosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

tert.-butyl lithium (594-19-4) + di-1-adamantylchlorophosphane (157282-19-4) → di(1-adamantyl)-tert-butylphosphine (321921-71-5)

Guidance literature:

With 1-Adamantyllithium; In n-heptane; for 1.5h; Heating;

Reference yield: 71.0%

1-iodo-butane (542-69-8) + bis(1-adamantyl)phosphine oxide (131266-79-0) → catacxium A (321921-71-5)

Guidance literature:

bis(1-adamantyl)phosphine oxide; With copper(II) trifluoromethanesulfonate; 1,1,3,3-Tetramethyldisiloxane; In toluene; at 100 ℃; for 9h; Inert atmosphere;

With cesiumhydroxide monohydrate; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

1-iodo-butane; In N,N-dimethyl-formamide; toluene; at 100 ℃; for 24h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja301764m

Reference yield: 48.0%

n-butyllithium (109-72-8,29786-93-4) + di-1-adamantylchlorophosphane (157282-19-4) → catacxium A (321921-71-5)

Guidance literature:

In tetrahydrofuran; hexane; for 1h; Heating;

upstream raw materials:

tert.-butyl lithium

di-1-adamantylchlorophosphane

(1-adamantyl)magnesium chloride

(1-adamantyl)dichlorophosphine

Downstream raw materials:

chloro[(di(1-adamantyl)-N-butylphosphine)-2-(2-aminobiphenyl)]palladium(II)

9-{5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-o-[4-(pyridin-4-yl)benzyl]-β-D-ribofuranosyl}-6-[2-(trimethylsilyl)ethoxy]-9H-purine

PdBr(P(C₄H₉)(C₁₀H₁₅)2)2(COC₆H₄CF₃)

PdBr(P(C₄H₉)(C₁₀H₁₅)2)2(C₆H₄CF₃)

Refernces

• 1、 Sergeev, Alexey G.,Spannenberg, Anke,Beller, Matthias. "Palladium-catalyzed formylation of aryl bromides: Elucidation of the catalytic cycle of an industrially applied coupling reaction". . p. 15549 - 15563. Retrieved 2009/03/12.
• 2、 -. "Production of novel phosphane ligands and use in catalytical reactions". . . Retrieved 2008/06/13.