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
• European Community (EC) Number: 691-708-4
• DSSTox Substance ID: DTXSID10463920
• Nikkaji Number: J1.424.674F
• Wikidata: Q72514204
• Mol file: 321921-71-5.mol

Synonyms:321921-71-5;BUTYLDI-1-ADAMANTYLPHOSPHINE;Di(adamantan-1-yl)(butyl)phosphine;CATACXIUM A;bis(1-adamantyl)-butylphosphane;Di(1-adamantyl)-n-butylphosphine;butyl di-1-adamantylphosphine;Butyldi(1-adamantanyl)phosphine;Bis(1-adamantyl)-butyl-phosphane;Bis(adamant-1-yl)(butyl)phosphine;MFCD05861606;n-butyldi-1-adamantylphosphine;di-1-Adamantyl-n-butylphosphine;BIS(ADAMANTAN-1-YL)(BUTYL)PHOSPHANE;BIS(ADAMANTAN-1-YL)(BUTYL)PHOSPHINE;butylbis(tricyclo[3.3.1.13,7]dec-1-yl)phosphine;n-butyl-di-adamantylphosphine;CatacXiumA;di(adamantan-1-yl)(butyl)phosphane;butyldiadamantylphosphine;butyldiadamantyl-phosphine;butyl diadamantyl phosphine;diadamantyl-n-butylphosphine;butyldi-1 adamantylphosphine;cataCXium(R) A, 95%;butyl di-1-adamantylphoshine;butyl-di-1-adamantylphosphine;butyldi(1-adamantyl)phosphine;butyldi-1-adamantyl phosphine;SCHEMBL128692;butyl di-1-adamantyl phosphine;butyl-di-1-adamantyl phosphine;di-1-adamantyl(butyl)phosphine;di-(adamantyl)-n-butylphosphine;n-butyl di-1-adamantylphosphine;SCHEMBL19588665;SCHEMBL20067101;SCHEMBL20077560;(bisadamantyl)-n-butyl-phosphane;C24H39P;DTXSID10463920;di(adamant-1-yl)(butyl)phosphine;di-(1-admantyl)-n-butylphosphine;HTJWUNNIRKDDIV-UHFFFAOYSA-N;di(1-adamantyl)-n-butyl-phosphine;di-(1-adamantyl)-n-butylphosphine;AMY19736;BCP04373;CS-D1800;di(adamantan-1-yl)(butyl)-phosphine;di(adamantan-1-yl)-(butyl)phosphine;AKOS015917431;AKOS017343282;CS-W001145;PB48236;AS-60432;BP-12241;SY009560;FT-0648862;EN300-177282;I11991;10.14272/HTJWUNNIRKDDIV-UHFFFAOYSA-N.1;A875675;doi:10.14272/HTJWUNNIRKDDIV-UHFFFAOYSA-N.1;J-520223;Y-200025;butyl-bis(tricyclo[3.3.1.13,7]dec-1-yl)-phosphine;butyl-bis(tricyclo[3.3.1.13.7]dec-1-yl)-phosphine;butylbis(tricyclo[3.3.1.13,7]dec-1-yl)-phosphine

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
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 358.278938242
• Heavy Atom Count: 25
• Complexity: 408

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:

• Canonical SMILES: CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5
• 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:

4-methoxyphenylacetylen

PdBr(P(C₄H₉)(C₁₀H₁₅)2)2(C₆H₄CF₃)

PdBr(P(C₄H₉)(C₁₀H₁₅)2)2(COC₆H₄CF₃)

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

Refernces

Sequential and selective Buchwald-Hartwig amination reactions for the controlled functionalization of 6-bromo-2-chloroquinoline: Synthesis of ligands for the Tec Src homology 3 domain

10.1021/jo801808r

The research focuses on the development of new 6-heterocyclic substituted 2-aminoquinolines using Buchwald-Hartwig amination reactions. These compounds are designed to have increased binding affinity for the Tec Src Homology 3 (SH3) domain, a protein-protein interaction domain that is a valuable target for therapeutic agents. The study explores the selective amination of an aryl bromide in the presence of an activated heteroaryl chloride, optimizing reaction conditions to achieve cross-coupling with various cyclic amines. Key chemicals involved in the research include 6-bromo-2-chloroquinoline as the starting material, palladium catalysts such as Pd(OAc)2, various phosphine ligands like CataCXium A (16), and bases like KOtBu and NaOtBu. The reactions also utilize a range of cyclic amines as coupling partners to introduce different heterocyclic substituents at the 6-position of the quinoline ring. The study further investigates the use of lithium bis(trimethylsilyl)amide (LHMDS) as an ammonia equivalent for the amination process to convert 2-chloroquinolines to 2-aminoquinolines, providing an improved method over traditional approaches. The binding affinity of the synthesized compounds with the Tec SH3 domain is assessed through NMR chemical shift perturbation analysis, revealing that the new ligands exhibit enhanced binding affinities compared to the lead compound, 2-aminoquinoline.

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