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Cas Database

591-51-5

591-51-5

Identification

  • Product Name:Lithium, phenyl-

  • CAS Number: 591-51-5

  • EINECS:209-720-1

  • Molecular Weight:84.0467

  • Molecular Formula: C6H5 Li

  • HS Code:29319090

  • Mol File:591-51-5.mol

Synonyms:Lithium,diphenyldi-; Phenyllithium

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Safety information and MSDS view more

  • Pictogram(s):

  • Hazard Codes:F,C,N,Xi

  • Signal Word:Danger

  • Hazard Statement:H250 Catches fire spontaneously if exposed to airH314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenyllithium solution 1.9M in dibutyl ether
  • Packaging:800ml
  • Price:$ 380
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenyllithium solution 1.9M in dibutyl ether
  • Packaging:100ml
  • Price:$ 64.6
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenyllithium solution 1.9M in dibutyl ether
  • Packaging:50ml
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Relevant articles and documentsAll total 60 Articles be found

Lithium Hexaphenylrhodate(III) and-Iridate(III): Structure in the Solid State and in Solution

Iwasaki, Takanori,Hirooka, Yuko,Takaya, Hikaru,Honma, Tetsuo,Nozaki, Kyoko

, p. 2489 - 2495 (2021)

Anionic homoleptic organo-Transition metal complexes can be prepared from organolithium reagents and transition metal salts and are key reactive intermediates in C-C bond formation. However, the interaction between the anionic component and cationic counterparts of multianionic homoleptic organo-Transition metal complexes in solution remains unclear, unlike well-studied monoanionic complexes such as organocuprates. Here we have prepared and structurally characterized lithium hexaphenylrhodate(III) and-iridate(III) complexes, [Li(12-crown-4)2][MPh6{Li(thf)}2] (M = Rh and Ir), as the first examples of hexaaryl complexes of d6 metals. In the crystals, two Li cations contact the trianionic MPh6 moiety, while the other exists as a solvent-separated ion pair. In THF, hexaphenylrhodate decomposed within 1 h. In contrast, the Ir analog was stable. 7Li NMR and X-ray absorption fine structure analysis revealed the solution-phase structure of hexaphenyliridate, which maintained a partially contacted ion pair structure even in THF, a coordinating solvent.

-

Broaddus

, p. 10,11-15 (1970)

-

CETONES PYRIDINIQUES. VIII. METALLATION REGIOSELECTIVE DE LA s-COLLIDINE: EFFETS DE METAUX ET DE SOLVANTS

Compagnon, P.-L.,Kimny, Tan

, p. 297 - 308 (1980)

The regioselective metalation of s-collidine yielding two anions, trapped by PhCN, was found to be essentially determined by the solvent and the size of the cation: twelve solvents and three cations (Li+, Na+, K+) were examined.The effect of various bases (alkali metals, phenyllithium, amides, "complex bases", amines) and of some metallic cations (Li+, Ag+, Pd2+) was studied.The solvent basicity was not responsible for the regioselectivity.

The Anionic Pathway in the Nickel-Catalysed Cross-Coupling of Aryl Ethers

Borys, Andryj M.,Hevia, Eva

supporting information, p. 24659 - 24667 (2021/10/20)

The Ni-catalysed cross-coupling of aryl ethers is a powerful method to forge new C?C and C?heteroatom bonds. However, the inert C(sp2)?O bond means that a canonical mechanism that relies on the oxidative addition of the aryl ether to a Ni0 centre is thermodynamically and kinetically unfavourable, which suggests that alternative mechanisms may be involved. Here, we provide spectroscopic and structural insights into the anionic pathway, which relies on the formation of electron-rich hetero-bimetallic nickelates by adding organometallic nucleophiles to a Ni0 centre. Assessing the rich co-complexation chemistry between Ni(COD)2 and PhLi has led to the structures and solution-state chemistry of a diverse family of catalytically competent lithium nickelates being unveiled. In addition, we demonstrate dramatic solvent and donor effects, which suggest that the cooperative activation of the aryl ether substrate by Ni0-ate complexes plays a key role in the catalytic cycle.

Phenylchromium(III) Chemistry Revisited 100 Years after Franz Hein (Part II): From LinCrPh3+ n(thf)x(n = 1, 2, 3) to Dimeric Triphenylchromate(II) Complexes

Fischer, Reinald,G?rls, Helmar,Suxdorf, Regina,Westerhausen, Matthias

, p. 3892 - 3905 (2020/11/13)

Polyphenylchromium(III) organometallics with various phenylation degrees and stabilized by diverse Lewis bases with various donor strengths and denticity were investigated in order to better understand the formation of (η6-arene)chromium complexes according to the procedure of Franz Hein (1892-1976) [ Organometallics 2019, 38, 498-511, DOI: 10.1021/acs.organomet.8b00811]. Part II focuses on hexa-, penta-, and tetraphenylchromates(III). Chromium(III) compounds with a lower phenylation degree will be discussed in a future part III. The numbering scheme of the complexes relates to the number of Cr-bound phenyl substituents. Hexaphenylchromate(III): The reaction of Ph3Cr(thf)3·0.25dx (3) (dx = 1,4-dioxane) with an ethereal solution of phenyllithium yields yellow-orange [Li3CrPh6(thf)2.3(OEt2)0.7] (6-thf-OEt2) which slowly degrades in contact with the reaction solution leading to emerald-green crystals of [{(Et2O)Li}2Ph3Cr(μ-O)]2 (3-Li2O). Pentaphenylchromate(III): Compound 6-thf-OEt2 reacts with 1 equiv of HCl-OEt2 solution to turquoise [{(thf)2Li}{(Et2O)Li}CrPh5] (5-thf-OEt2) that reacts with THF to the green contact ion pair [{(thf)2Li}2CrPh5] (5-thf) and with 12-crown-4 (12C4) to the light green solvent-separated ion pair [(12C4)Li(thf)]2 [CrPh5] (5-thf-12C4). Refluxing of 5-thf-OEt2 in diethyl ether leads to ether degradation and formation of 3-Li2O, whereas 5-thf-12C4 liberates biphenyl under similar reaction conditions. Tetraphenylchromate(III): The reaction of 3 with 1 equiv of phenyllithium in THF leads to a green reaction mixture. At -50 °C, red [(thf)4Li] [cis-(thf)2CrPh4]·2THF (4-thf) crystallizes which reversibly transforms into a green oil above -50 °C. Upon acidolysis of 5-thf-OEt2 with 1 equiv of HCl-OEt2 at -20 °C, the intermediately formed red complex is reduced to the dinuclear chromate(II) [{(thf)Li}CrPh3]2 (3-CrII-thf) (Cr-Cr 187.66(8) pm). Recrystallization of this product from THF yields solvent-separated [(thf)4Li]2 [(CrPh3)2] (3-CrII-thf4) with a Cr-Cr quadruple bond (Cr-Cr 183.7(2) pm) without contacts between the lithium ions and Cr-bound phenyl groups. Complex 3-CrII-thf reacts at room temperature in diethyl ether to the sandwich complexes bis(biphenyl)chromium(0) [(η6-Ph2)2Cr0] (π-4) and benzene-biphenylchromium(0) [(η6-C6H6)(η6-Ph2)Cr0] (π-3). Compounds in bold letters are authenticated by X-ray structure determinations.

Generation of Phosphonium Sites on Sulfated Zirconium Oxide: Relationship to Br?nsted Acid Strength of Surface -OH Sites

Rodriguez, Jessica,Culver, Damien B.,Conley, Matthew P.

supporting information, p. 1484 - 1488 (2019/01/25)

The reaction of (tBu)2ArP (1a-h), where the para position of the Ar group contains electron-donating or electron-withdrawing groups, with sulfated zirconium oxide partially dehydroxylated at 300 °C (SZO300) forms [(tBu)2ArPH][SZO300] (2a-h). The equilibrium binding constants of 1a-h to SZO300 are related to the pKa of [(tBu)2ArPH]; R3P that form less acidic phosphoniums (high pKa values) bind stronger to SZO300 than R3P that form more acidic phosphoniums (low pKa values). These studies show that Br?nsted acid sites on the surface of SZO300 are not superacidic.

Dichotomy within 1,4-addition of organolithium and Grignard reagents to α,β-unsaturated Fischer alkoxycarbenes: A new synthesis of Fischer carbenes

Tobrman, Tomá?,Polák, Peter,?ubiňák, Marek,Dvo?áková, Hana,Dvo?ák, Dalimil

, p. 2175 - 2181 (2019/03/05)

The reaction of organolithium and Grignard reagents with pentacarbonyl[(ethoxy)(2-phenylethenyl)carbene]chromium(0) gave, after the quenching of the initially formed product of the 1,4-addition, different products depending on the organometallic and quenching reagents used. The addition of organolithiums, followed by a work-up with acid (AcOH or HCl), afforded the corresponding carbene complexes. In contrast, quenching the reaction mixture with ethanol led to the stereoselective formation of (Z)-enol ethers. The usage of Grignard reagents led to the formation of the carbene complexes regardless of which quenching reagent was used.

Process route upstream and downstream products

Process route

iodobenzene
591-50-4

iodobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With n-butyllithium; In hexane; at -78 - 25 ℃; for 1h; Inert atmosphere;
100%
With n-butyllithium; In hexane; benzene; at 20 ℃; for 16h;
91%
With n-butyllithium; In benzene; for 0.333333h; Ambient temperature;
With n-butyllithium; In pentane; Ambient temperature;
With tert.-butyl lithium; In diethyl ether; -78 deg C, 0.5 h; RT, 1 h;
With n-butyllithium; In tetrahydrofuran; at -86 ℃;
With n-butyllithium; In pentane; at 20 ℃; Inert atmosphere;
With n-butyllithium; In hexane; at 0 ℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;
bromobenzene
108-86-1,52753-63-6

bromobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With lithium; In diethyl ether; ultrasonic agitation;
95%
In dibutyl ether; at 10 - 30 ℃; Reagent/catalyst; Temperature; Inert atmosphere; Large scale;
80%
With diethyl ether; lithium; man erhitzt schliesslich unter Zugabe von Aether zum Sieden;
With n-butyllithium; In hexane; pentane; at 20 ℃; in evacuated, closed vessel;
With n-butyllithium; In tetrahydrofuran; at -78 ℃;
With lithium; In diethyl ether;
With lithium; In diethyl ether; for 2h;
With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;
With n-butyllithium; In hexane; at 40 ℃; Kinetics; Thermodynamic data; influence of p-methylanisole, Ea;
With sec.-butyllithium; In tetrahydrofuran-d8;
With lithium;
With lithium; In water;
With lithium; In diethyl ether; at 20 ℃; Inert atmosphere;
With n-butyllithium; In hexane;
With lithium;
With n-butyllithium; In tetrahydrofuran; at -86 ℃; for 0.0111111h;
With lithium; In diethyl ether; for 2h; Concentration; Inert atmosphere; Reflux;
With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;
With tert.-butyl lithium;
n-butyllithium
109-72-8,29786-93-4

n-butyllithium

bromobenzene
108-86-1,52753-63-6

bromobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
In hexanes;
In tetrahydrofuran; hexane; at -78 ℃;
In hexane; at -80 - 20 ℃; for 48h; Inert atmosphere;
In diethyl ether; at -78 ℃;
α-picoline
109-06-8

α-picoline

bromobenzene
108-86-1,52753-63-6

bromobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With hydrogenchloride; sodium carbonate; In ethanol; sodium;
With lithium; In sodium;
With lithium; diisopropylamine;
diphenylmercury(II)
587-85-9,1337-09-3

diphenylmercury(II)

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With lithium; In diethyl ether; Inert atmosphere; Schlenk technique;
74%
With lithium; benzene;
bromobenzene
108-86-1,52753-63-6

bromobenzene

cyclohexyllithium
10074-42-7

cyclohexyllithium

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
In tetrahydrofuran; at -55 ℃; for 3h;
butyl methyl ether
628-28-4

butyl methyl ether

lithium hydride
7580-67-8

lithium hydride

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With phenyllithium; In dibutyl ether; chlorobenzene;
bromobenzene
108-86-1,52753-63-6

bromobenzene

2,4-O-benzylidene-D-tetraose
909277-52-7

2,4-O-benzylidene-D-tetraose

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With lithium; In tetrahydrofuran; methanol; diethyl ether; water;
bromobenzene
108-86-1,52753-63-6

bromobenzene

CH3 I

CH3 I

3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
60628-57-1

3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

3-fluorodiazepam

3-fluorodiazepam

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
With lithium; In tetrahydrofuran; nitrogen;
n-butyllithium
109-72-8,29786-93-4

n-butyllithium

iodobenzene
591-50-4

iodobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
Conditions Yield
In tetrahydrofuran; hexanes; at -78 ℃; for 0.333333h;

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