Lithium, (dimethylphenylsilyl)-

Base Information

• Chemical Name: Lithium, (dimethylphenylsilyl)-
• CAS No.: 3839-31-4
• Molecular Formula: C8H11LiSi
• Molecular Weight: 142.202
• DSSTox Substance ID: DTXSID10449966
• Mol file: 3839-31-4.mol

Synonyms:phenyldimethylsilyllithium;PhMe2SiLi

Chemical Property of Lithium, (dimethylphenylsilyl)-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 142.07900532
• Heavy Atom Count: 10
• Complexity: 77.3

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].C[Si-](C)C1=CC=CC=C1

Technology Process of Lithium, (dimethylphenylsilyl)-

There total 6 articles about Lithium, (dimethylphenylsilyl)- 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:

phenyldimethylsilyl chloride (768-33-2) → dimethyl(phenyl)silyl lithium (3839-31-4)

Guidance literature:

With lithium; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jo011157s

Reference yield:

phenyldimethylsilyl chloride (768-33-2) → dimethyl(phenyl)silyllithium (3839-31-4)

Guidance literature:

With lithium; In tetrahydrofuran; at -8 ℃; for 36h;

DOI:10.1039/P19810002527

Reference yield:

1,2-diphenyltetramethyldisilane (1145-98-8) → dimethyl(phenyl)silyllithium (3839-31-4)

Guidance literature:

With lithium; In tetrahydrofuran; at -5 ℃;

DOI:10.1016/0040-4020(89)80083-3

upstream raw materials:

1,2-diphenyltetramethyldisilane

phenyldimethylsilyl chloride

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

Downstream raw materials:

1,1,1,2,2-pentamethyl-2-phenyldisilane

(diphenylmethoxy)(phenyl)dimethylsilane

2,2-Dimethyl-1,1,1,2-tetraphenyldisilan

Tris-dimethylphenylsilyl-silan

Refernces

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

10.1021/acs.orglett.1c02173

The research presents a novel method for enone transposition using a silyl group masking strategy. The purpose of the study was to develop a reliable and efficient method for transposing enones, which are versatile intermediates in organic synthesis, with highlights such as enantioswitching, substituent shuffling, and Z-selectivity. The researchers utilized key chemicals like PhMe2SiLi (phenyldimethylsilyllithium) for the addition to carbonyl groups, acetonitrile and water as solvents, and TFA (trifluoroacetic acid) for catalysis. The developed method was successfully applied to the first total synthesis and structural revision of peribysin D, a bioactive natural product, as well as the formal synthesis of E-guggulsterone and E-volkendousin. The study concludes that the silyl-based masking group approach is highly effective for enone transposition, offering a practical and versatile tool for organic synthesis, with potential applications in the synthesis of other bioactive compounds and natural products.

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