Lithium, (diphenylmethyl)-

Base Information

• Chemical Name: Lithium, (diphenylmethyl)-
• CAS No.: 881-42-5
• Molecular Formula: C13H11Li
• Molecular Weight: 174.171
• DSSTox Substance ID: DTXSID20455351
• Mol file: 881-42-5.mol

Synonyms:Diphenylmethyllithium;Lithium, (diphenylmethyl)-;lithio diphenylmethane;881-42-5;(Ph)2CHLi;DTXSID20455351;UXXAPTACMRJCDK-UHFFFAOYSA-N

Chemical Property of Lithium, (diphenylmethyl)-

Chemical Property:

• PSA: 0.00000
• LogP: 3.28730
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.10207879
• Heavy Atom Count: 14
• Complexity: 116

Purity/Quality:

99% ,98%,Electron Grade , ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].C1=CC=C(C=C1)[CH-]C2=CC=CC=C2
• General Description: Lithium, (diphenylmethyl)-, also known as benzhydryllithium, is a reactive organolithium compound used in stereochemical studies, such as its reaction with (R)-(+)-α-phenylneopentyl chloride, where the optical purity of reactants influences the configuration of the resulting product. Its role in such reactions highlights its utility in probing stereochemical outcomes in organic synthesis.

Technology Process of Lithium, (diphenylmethyl)-

There total 14 articles about Lithium, (diphenylmethyl)- 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: 80.0%

Diphenylmethane (101-81-5) → diphenylmethyllithium (881-42-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201200278

Reference yield:

Diphenylmethane (101-81-5) + C8H16N(1-)*Li(1+) (110426-39-6) → N-ethyl-cyclohexanamine (5459-93-8) + diphenylmethyllithium (881-42-5)

Guidance literature:

In tetrahydrofuran; at 30 ℃; Equilibrium constant;

DOI:10.1016/S0040-4020(01)82054-8

Reference yield:

Diphenylmethane (101-81-5) + lithium isopropyl(methyl)amide (82881-55-8) → N-methylpropan-2-amine (4747-21-1) + diphenylmethyllithium (881-42-5)

Guidance literature:

In tetrahydrofuran; at 30 ℃; Equilibrium constant;

DOI:10.1016/S0040-4020(01)82054-8

upstream raw materials:

n-butyllithium

diethyl ether

Diphenylmethane

lithium diethylamide

Downstream raw materials:

N,N-dimethyl-3,3-diphenylpropan-1-amine

(3,3-Diphenylpropyl)carbamidsaeure-ethylester

4,4-diphenyl-1-butanol

1,1-diphenyl-3-pentanol

Refernces

Configuration Determination of (R)-(-)-1,1,2-Triphenyl-3,3-dimethylbutane and the Stereochemistry of the Reaction of Benzhydryllithium with (R)-(+)-α-Phenylneopentyl Chloride

10.1021/jo00139a027

The research explores various aspects of organic chemistry, focusing on the reactions of hemiacetal esters with acids and alcohols, the synthesis and configuration determination of (R)-(-)-1,1,2-triphenyl-3,3-dimethylbutane, and the nitrogen-15 NMR and photoelectron spectroscopy of substituted N-phenylaziridines. The first study investigates the formation of mixed acetals and the thermolysis of hemiacetal esters using NMR spectroscopy, aiming to understand reaction mechanisms and equilibrium states. The second study synthesizes (R)-(-)-1,1,2-triphenyl-3,3-dimethylbutane and examines the stereochemistry of reactions involving benzhydryllithium and α-phenylneopentyl chloride, concluding that the optical purity of starting materials significantly affects the final product's configuration. The third study measures the 15N chemical shifts of N-arylaziridines and correlates them with shifts in anilines and anisoles, revealing high resonance dependence and smaller-than-expected steric effects. Key chemicals used across these studies include hemiacetal ester, acetic acid, diphenylmethyllithium, α-phenylneopentyl chloride, thionyl chloride, phosgene, and various substituted N-phenylaziridines.