766-04-1

Basic information

• Product Name: BENZYLLITHIUM
• Synonyms: BENZYLLITHIUM;LithiuM,(phenylMethyl)-
• CAS NO: 766-04-1
• Molecular Formula: C₇H₇Li
• Molecular Weight: 98.07
• Mol File: 766-04-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BENZYLLITHIUM(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLLITHIUM(766-04-1)
• EPA Substance Registry System: BENZYLLITHIUM(766-04-1)

Safety Data

• Hazardous Substances Data: 766-04-1(Hazardous Substances Data)

Upstream product

• 109-72-8 n-butyllithium 
• 780-24-5 dibenzylmercury(II) 
• 917-54-4 methyllithium 
• 811-49-4 ethyllithium 
• 60-29-7 diethyl ether 
• 100-44-7 benzyl chloride 
• 591-51-5 phenyllithium 
• 6921-34-2 benzylmagnesium chloride 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 28493-54-1 benzyltributyltin 
• 75356-81-9 1-Phenylpropyllithium 
• 831-91-4 Benzyl phenyl sulfide 
• 17179-20-3 p-methoxybenzyllithium 

Downstream Products

• 89-95-2 2-methyl-benzyl alcohol 
• 564467-88-5 1-benzyl-2-methyl-isoindole 
• 1177-69-1 2-benzyl-2,4,6-triphenyl-2H-pyran 
• 51307-04-1 1,5-diphenyl-2,4-pentanedione 
• 18866-37-0 tribenzyl-octyl-silane 
• 5410-07-1 benzyl(triphenyl)silane 
• 14752-75-1 n-heptadecylbenzene 
• 10539-18-1 3,4,5-triphenyl-4,5-dihydro-1H-pyrazole 
• 538-68-1 pentylbenzene 
• 1081-77-2 n-nonylbenzene 
• 123-02-4 tridecylbenzene 
• 53317-09-2 B-benzyl-9-BBN 
• 1745-16-0 (E)-3-pentenylbenzene 
• 27286-19-7 benzyl(di-tert-butyl)phosphane 

Relevant articles and documents

Phosphorus-Containing Block Copolymers from the Sequential Living Anionic Copolymerization of a Phosphaalkene with Methyl Methacrylate

Although living polymerization methods are widely applicable to organic monomers, their application to inorganic monomers is rare. For the first time, we show that the living poly(methylenephosphine) (PMPn?) anion can function as a m

Directional properties of fluorenylidene moieties in unsymmetrically substituted N-heterocyclic carbenes. Unexpected CH activation of a methylfluorenyl group with palladium. Use in palladium catalysed Suzuki-Miyaura cross coupling of aryl chlorides

Benzimidazolium salts having their two nitrogen atoms substituted by different 9-alkylfluorenyl groups (4a-e and 4g, alkyl1/alkyl 2 = Me/Et, Me/Pr, Me/n-Bu, Me/i-Pr, Me/Bn, Me/CH2SMe have been synthesised in high yields in two or three steps from N,N′-bis(9H- fluoren-9-ylidene)benzene-1,2-diamine (1). The imidazolium salts 4a-e were converted readily into the corresponding PEPPSI-type palladium complexes (PEPPSI = pyridine-enhanced precatalyst preparation stabilisation and initiation), while reaction of the methylthioether-substituted salt 4g with PdCl 2/K2CO3/pyridine afforded the palladacycle 5g resulting from metallation of the methyl group attached to the fluorenylidene moiety. NMR and X-ray diffraction studies revealed that the carbene ligands in 5a-5e behave as clamp-like ligands, the resulting metal confinement arising from a combination of the orientational properties of the fluorenylidene moieties that push the alkyl groups towards the metal centre and attractive anagostic interactions involving CH2(fluorenyl) groups. Complexes 5a-e were assessed in Suzuki-Miyaura cross-coupling reactions. Like their symmetrical analogues they displayed high activity in the coupling of phenyl boronic acid with p-tolylchloride but their performance remained slightly inferior to that of the related, symmetrical Et/Et complex 5h.

Isomerization polymerization of the phosphaalkene MesP=CPh2: An alternative microstructure for poly(methylenephosphine)s

Unique pathway: The radical-initiated addition polymerization of MesP=CPh2 propagates through the ortho-bound CH3 group of the Mes moiety after C-H bond activation (see scheme, Mes=2,4,6-trimethylphenyl, tht=tetrahydrothiophene, TEMPO=2,2,6,6-tetramethyl-l-piperidinoxyl). This unique isomerization polymerization mechanism contrasts the previously suggested head-to-tail enchainment typically observed for olefins. Copyright

Arylcalcium iodides in tetrahydropyran: Solution stability in comparison to aryllithium reagents

Reduction of para-substituted iodobenzene in tetrahydropyran (THP) with finely dispersed calcium powder yields arylcalcium iodides of the type [(THP)4Ca(C6H4-4-R)I] with R = CH3 (1), Cl (2), Br (3), I (4), OCH3 (5). A 2-fold insertion of calcium into dihalobenzenes was not observed. The β-naphthylcalcium iodide [(THP)4Ca(β-Naph)I] (6) is also accessible by direct synthesis in THP. The durability of arylcalcium compounds in THP was studied in comparison to that in THF, and a slightly enhanced lifetime in THP at ambient temperature was observed. Furthermore, the relative reactivity and selectivity of 1 and its lithium counterpart [{(THP)2Li}2(μ-Tol)(μ-Br)] (7) in the reaction with THP and THF were studied. α-Metalation and subsequent cycloreversion was the major pathway observed for THF in both cases. In the degradation reaction induced by 7, several byproducts arising from carbolithiation and, surprisingly, from β-metalation reactions were identified, while 1 was found to be more selective. The related [(THP) 2Li(μ-Ph)]2 (9) was prepared and used to unambiguously identify some of the products. In order to verify the formation of benzyllithium as one of the byproducts, an authentic sample of [(dme)Li(μ-CH 2Ph]2 (8) was prepared. In THP, an inversion of the relative reactivity of 1 and 7 was observed and the calcium compound was found to be more reactive than its lithium analogue. The crystal structures of 1-9 were determined by X-ray diffraction studies, and a trans arrangement of the anionic ligands due to electrostatic reasons was observed in case of the hexacoordinated calcium complexes.

Production of benzyllithium, benzylsodium, and polyphenylene paradimethylene

A process for producing benzyllithium, benzylsodium and polyphenylene paradimethylene and analogs comprising dissolving toluene in an aprotic polar solvent in which toluene is more acidic than water, such as DMSO, under an inert atmosphere, such as argon, adding an alkali metal hydroxide, such as lithium or sodium hydroxide, to form the alkali metal anion of the benzyl cation and water then removing the solvent and water to obtain the solid alkali metal alpha-carbon toluene compound, which is best stored under hexane. This process also relating to toluene analogs such as parachloro toluene which thereby yields parachloro alkali metal alpha-carbon toluene which is then polymerized by heating with a suitable high-boiling solvent, such as dibutyl ether or dimethoxy ethane in the presence of a copper catalyst, such as copper sulfate or finely divided copper metal at approximately 170C for 5 hours to form polyphenylene paradimethylene. This process having the advantage of using alkali metal hydroxides instead of elemental alkali metals, a reaction occurring at ordinary temperatures, and a lower cost of the product. This process also allowing the economical production of polyphenylene paradimethylene which is not currently being manufactured.

1,3,5-SUBSTITUTED PHENYL DERIVATIVE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE

The present invention is directed to 1,3,5-phenyl substituted derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

Reductive lithiation of alkyl phenyl sulfides in diethyl ether. A ready access to α,α-dialkylbenzyllithiums

Diethyl ether is a convenient solvent for the conversion of benzylic phenyl sulfides to the corresponding organolithiums by an uncatalyzed reductive metalation, while catalysis by naphthalene is required to achieve the same reaction for alkyl phenyl sulfides. The addition of magnesium 2-ethoxyethoxide to solutions of unstable alkyllithiums prepared in this way provides storable reagents.

ROMPgel-supported biphenyl and naphthalene: Reagents for lithiation reactions with minimal purification

The synthesis of ring opening metathesis, polymer (ROMPgel) supported naphthalene and biphenyl reagents was carried out. These reagents were utilized for catalytic lithiation reactions of aryl and alkyl chlorides and for the reductive deprotection of benzyl and allyl ethers.

Intermediates for the preparation of cyclic urea

This invention relates to novel compounds and derivatives thereof containing a trioxepane protected diol in addition to a hydrazone, hydrazine, amine, or cyclic urea moiety; methods for the preparation of said compounds; and the use of said compounds in p

The preparation of pure allyl- and benzyl-type organoalkali intermediates via organotin compounds

Superbase metalation of alkenes or alkylbenzenes and subsequent condensation with trialkylstannyl chloride affords allyl- or benzyl-type organotin compounds that can be isolated in pure form.Treatment with soluble reagents such as methyllithium, trimethylsilylmethylpotassium and trimethylsilylmethylcaesium generates the corresponding organoalkali derivatives almost quantitatively and in high purity, suitable for kinetic or spectroscopic studies.