Lithium, [(phenylthio)methyl]-

Base Information

• Chemical Name: Lithium, [(phenylthio)methyl]-
• CAS No.: 13307-75-0
• Molecular Formula: C7H7LiS
• Molecular Weight: 130.14
• DSSTox Substance ID: DTXSID70447943
• Mol file: 13307-75-0.mol

Synonyms:phenylthiomethyllithium;Lithium, [(phenylthio)methyl]-;13307-75-0;Phenylthiomethyl lithium;(phenylthio) methyllithium;SCHEMBL8014099;DTXSID70447943;QAHPMEROKBCURL-UHFFFAOYSA-N

Chemical Property of Lithium, [(phenylthio)methyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 130.04284983
• Heavy Atom Count: 9
• Complexity: 59.9

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].[CH2-]SC1=CC=CC=C1

Technology Process of Lithium, [(phenylthio)methyl]-

There total 5 articles about Lithium, [(phenylthio)methyl]- 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: 58.0%

methyl-phenyl-thioether (100-68-5) → (phenylthio)methyllithium (13307-75-0)

Guidance literature:

With phenyllithium; In tetrahydrofuran; diethyl ether; at 0 ℃; for 30h;

DOI:10.1016/0022-328X(84)80570-7

Reference yield:

methyl-phenyl-thioether (100-68-5) + 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (72431-10-8) → (phenylthio)methyllithium (13307-75-0)

Guidance literature:

With phenyllithium; In tetrahydrofuran;

Reference yield:

1,4-diaza-bicyclo[2.2.2]octane (280-57-9,88935-43-7) + methyl-phenyl-thioether (100-68-5) → (phenylthio)methyllithium (13307-75-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

upstream raw materials:

methyl-phenyl-thioether

1,4-diaza-bicyclo[2.2.2]octane

10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Downstream raw materials:

1-iodo-n-undecane

1-(phenylthio)undecane

1-Phenylsulfanyl-2-phenylsulfanylmethyl-undecan-2-ol

2-Phenylsulfanylmethyl-cyclohex-1-enecarbaldehyde

Refernces

A synthesis of (+)-milbemycin β₃. The 3,4-dihydro-2H-pyran approach

10.1039/c39850001388

The research focuses on the synthesis of (+)-milbemycin p3, an important compound in the field of organic chemistry. The purpose of the study was to develop a more practical and cost-effective alternative synthesis method compared to the previously reported directed aldol approach. The new method employed the 3,4-dihydro-2H-pyran approach, which was highly convergent and utilized inexpensive chiral precursors. Key steps in the synthesis included nucleophilic scission of oxirane by vinyl alanate and metallated 3,4-dihydro-2H-pyran. The chemicals used in the process included phenylthiomethyl-lithium, aldehyde (5), vinyl alanate (4), acetylene (3), and metallated 3,4-dihydro-2H-pyran (15), among others. The conclusions of the research indicated that all reactions could be performed on a substantial scale, yielding products that were easily purified, making this approach more practical than the directed aldol method. The study also highlighted the importance of stereoselective synthesis of the spiroacetal moiety and the C(14)-C(15) trisubstituted double bond in the overall synthesis process.