Product Name

  • Name

    Phenyllithium

  • EINECS 209-720-1
  • CAS No. 591-51-5
  • Article Data87
  • CAS DataBase
  • Density 0.835
  • Solubility vigorous reaction
  • Melting Point 160-163 °C(Solv: benzene (71-43-2))
  • Formula C6H5 Li
  • Boiling Point 140-143 ºC
  • Molecular Weight 84.0467
  • Flash Point 20 ºC
  • Transport Information UN 3392
  • Appearance Colorless transparent to yellow liquid
  • Safety Incompatible with air, water. Product of reaction with titanium tetraethoxide ignites spontaneously in air and reacts violently with water. When heated to decomposition it emits toxic fumes of Li2O. See also LITHIUM COMPOUNDS and ORGANOMETALS.
  • Risk Codes R11;R14;R35;R52/53   
  • Molecular Structure Molecular Structure of 591-51-5 (Phenyllithium)
  • Hazard Symbols
  • Synonyms Lithium,diphenyldi-; Phenyllithium
  • PSA 0.00000
  • LogP 1.48680

Synthetic route

bromobenzene
108-86-1

bromobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
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;
N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole
915703-81-0

N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole

tert-butylamine
75-64-9

tert-butylamine

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
In benzene at 80℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique;84%
diphenylmercury(II)
587-85-9

diphenylmercury(II)

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With lithium In diethyl ether Inert atmosphere; Schlenk technique;74%
With lithium; benzene
triphenylbismuthane
603-33-8

triphenylbismuthane

lithium
7439-93-2

lithium

A

bismuth
7440-69-9

bismuth

B

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
In diethyl ether 20°C;A n/a
B 22%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

bromobenzene
108-86-1

bromobenzene

diethyl ether
60-29-7

diethyl ether

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

hexaphenyl diplumbane
3124-01-4

hexaphenyl diplumbane

A

hexabutyldiplumbum
27980-18-3

hexabutyldiplumbum

B

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

diphenylmagnesium
555-54-4

diphenylmagnesium

A

dibutylmagnesium
1191-47-5

dibutylmagnesium

B

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
reversible Reaktion;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diphenylselenide
1132-39-4

diphenylselenide

A

butyl phenyl selenide
28622-61-9

butyl phenyl selenide

B

Benzeneselenol
645-96-5

Benzeneselenol

C

phenyllithium
591-51-5

phenyllithium

diethyl ether
60-29-7

diethyl ether

methyllithium
917-54-4

methyllithium

Tetraphenyllead
595-89-1

Tetraphenyllead

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
analoge Umsetzungen erfolgen mit Tetrakis-<4-chlor-phenyl>-zinn und mit Dibenzylquecksilber;
ethyllithium
811-49-4

ethyllithium

triphenylantimony
603-36-1

triphenylantimony

phenyllithium
591-51-5

phenyllithium

ethyllithium
811-49-4

ethyllithium

diphenylmercury(II)
587-85-9

diphenylmercury(II)

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With benzene
ethyllithium
811-49-4

ethyllithium

diphenylmercury(II)
587-85-9

diphenylmercury(II)

A

diethylmercury
627-44-1

diethylmercury

B

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

tetraphenyltin(IV)
595-90-4

tetraphenyltin(IV)

benzene
71-43-2

benzene

A

tetra-n-butyltin(IV)
1461-25-2

tetra-n-butyltin(IV)

B

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
anal.R.mit Tetrakis-<4-chlor-phenyl>-zinn, Tetraphenylblei, Diphenyl-di-p-tolyl-blei, Tetra-p-tolyl-blei, Triphenylblei und Tri-p-tolyl-blei;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

Tetraphenyllead
595-89-1

Tetraphenyllead

benzene
71-43-2

benzene

A

tetra-n-butyl lead
1920-90-7

tetra-n-butyl lead

B

phenyllithium
591-51-5

phenyllithium

iodobenzene
591-50-4

iodobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
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;
triphenyl-arsane
603-32-7

triphenyl-arsane

(14C)-Phenyllithium

(14C)-Phenyllithium

A

phenyllithium
591-51-5

phenyllithium

B

(14)C18H15As

(14)C18H15As

Conditions
ConditionsYield
In tetrahydrofuran; benzene at 24.9℃; Rate constant; Kinetics; Thermodynamic data; var. solvents; E, ΔH(excit.), ΔS(excit.), ΔG(excit.);
1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

A

phenyllithium
591-51-5

phenyllithium

B

1,3-bis(lithiumphenylphosphido)propane
60778-68-9

1,3-bis(lithiumphenylphosphido)propane

Conditions
ConditionsYield
With lithium In tetrahydrofuran
1,5-bis-(diphenylphosphino)pentane
27721-02-4

1,5-bis-(diphenylphosphino)pentane

A

phenyllithium
591-51-5

phenyllithium

B

1,5-Bis--pentamethylen
115241-59-3

1,5-Bis--pentamethylen

Conditions
ConditionsYield
With lithium In tetrahydrofuran
C12H10I(1-)*Li(1+)
120416-98-0

C12H10I(1-)*Li(1+)

A

iodobenzene
591-50-4

iodobenzene

B

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With 1-iodo-butane In tetrahydrofuran at -78℃; Equilibrium constant; solvent effect;
bicyclo<1.1.1>pentyl phenyl sulfide
98585-81-0

bicyclo<1.1.1>pentyl phenyl sulfide

A

lithium thiophenoxide
2973-86-6

lithium thiophenoxide

B

C5H7Li
117632-98-1

C5H7Li

C

Lithium; bicyclo[1.1.1]pentane-1-thiolate
117633-17-7

Lithium; bicyclo[1.1.1]pentane-1-thiolate

D

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With 4,4'-di-tert-butylbiphenyl; lithium at -60℃;
1,2-diphenyl-3,4-di-t-butyldiphosphete
75600-54-3, 96693-29-7

1,2-diphenyl-3,4-di-t-butyldiphosphete

A

phenyllithium
591-51-5

phenyllithium

B

(2-phenyl-3,4-di-tert-butyl-1,2-diphosphetenyl)lithium
96693-31-1

(2-phenyl-3,4-di-tert-butyl-1,2-diphosphetenyl)lithium

Conditions
ConditionsYield
With lithium In tetrahydrofuran Product distribution; Ambient temperature;
chlorobenzene
108-90-7

chlorobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at -78℃; for 0.75h; various react. cond.; diff. chloroarenes; further reaction with electrophiles;
With lithium; lithium hydride; biphenyl In dibutyl ether at 35℃; for 6h;
With lithium In tetrahydrofuran at -25℃;
1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

A

phenyllithium
591-51-5

phenyllithium

B

1,4-Bis--tetramethylen
115241-57-1

1,4-Bis--tetramethylen

Conditions
ConditionsYield
With lithium In tetrahydrofuran
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diphenylmercury(II)
587-85-9

diphenylmercury(II)

benzene
71-43-2

benzene

petroleum ether

petroleum ether

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

bromobenzene
108-86-1

bromobenzene

petroleum ether

petroleum ether

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

diphenyl-bis-<4-chloro-phenyl>-lead

diphenyl-bis-<4-chloro-phenyl>-lead

A

4-chlorophenyl lithium
14774-78-8

4-chlorophenyl lithium

B

phenyllithium
591-51-5

phenyllithium

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

triphenyl-<4-chloro-phenyl>-lead

triphenyl-<4-chloro-phenyl>-lead

A

4-chlorophenyl lithium
14774-78-8

4-chlorophenyl lithium

B

phenyllithium
591-51-5

phenyllithium

tert.-butyl lithium
594-19-4

tert.-butyl lithium

diphenylmercury(II)
587-85-9

diphenylmercury(II)

benzene
71-43-2

benzene

petroleum ether

petroleum ether

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
mit Dibenzylquecksilber erfolgt eine analoge Umsetzung;
fluorobenzene
462-06-6

fluorobenzene

phenyllithium
591-51-5

phenyllithium

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at -30℃; for 0.583333h; lithiation;
phenyllithium
591-51-5

phenyllithium

S-Phenyldibenzothiophenium

S-Phenyldibenzothiophenium

phenyl o-terphenyl sulfide
34884-36-1

phenyl o-terphenyl sulfide

Conditions
ConditionsYield
Mechanism; 1.) THF, cyclohexane, ether, -100 deg C, 2.) THF, cyclohexane, ether, room temp.;100%
Stage #1: phenyllithium With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: S-Phenyldibenzothiophenium In tetrahydrofuran; hexane at -78 - 23℃; for 1.5h; Inert atmosphere;
100%
In tetrahydrofuran
phenyllithium
591-51-5

phenyllithium

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine
68981-86-2

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1,4-dihydro-4-phenylpyridine
68981-78-2

3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1,4-dihydro-4-phenylpyridine

Conditions
ConditionsYield
In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) 0 deg C, 1 h;100%
In tetrahydrofuran at -78℃; for 0.166667h;82%
In diethyl ether for 1h; Ambient temperature;78.6%
2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

phenyllithium
591-51-5

phenyllithium

(2-Benzothiazolyl)methyllithium
125414-91-7

(2-Benzothiazolyl)methyllithium

Conditions
ConditionsYield
In diethyl ether; benzene at -78℃;100%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

phenyllithium
591-51-5

phenyllithium

(E)-1,3-diphenyl-1-trimethylsilyloxy-2-propene
94740-99-5

(E)-1,3-diphenyl-1-trimethylsilyloxy-2-propene

Conditions
ConditionsYield
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran Further stages.;
100%
1) THF, -20 deg C, 15 min; 2) THF, RT, 12 h; Yield given. Multistep reaction;
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

phenyllithium
591-51-5

phenyllithium

(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose
118436-89-8, 118436-90-1

(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose

Conditions
ConditionsYield
at -78℃;100%
In tetrahydrofuran 1.) -78 deg C, 2 h, 2.) from -78 deg C to room temperature, 2 h;85.7%
In tetrahydrofuran at -78℃;
1,4,5,6,7,7a-hexahydro-inden-2-one
39163-29-6, 117780-10-6

1,4,5,6,7,7a-hexahydro-inden-2-one

phenyllithium
591-51-5

phenyllithium

2-phenyl-2,4,5,6,7,7a-hexahydro-1H-inden-2-ol
536976-47-3

2-phenyl-2,4,5,6,7,7a-hexahydro-1H-inden-2-ol

Conditions
ConditionsYield
In diethyl ether; cyclohexane at 0 - 20℃; for 2h;100%
With cerium(III) chloride 1.) THF, -20 deg C, 0.5 h, 2.) THF, from -78 deg C to RT; Multistep reaction;
2-Methyl-2-(tert-butylperoxy)cyclohexanon
25462-04-8

2-Methyl-2-(tert-butylperoxy)cyclohexanon

phenyllithium
591-51-5

phenyllithium

2-tert-Butylperoxy-2-methyl-1-phenyl-cyclohexanol
109139-15-3, 109139-16-4

2-tert-Butylperoxy-2-methyl-1-phenyl-cyclohexanol

Conditions
ConditionsYield
In diethyl ether at -78℃; for 0.666667h;100%
1,4-diiodocubane
97229-08-8

1,4-diiodocubane

phenyllithium
591-51-5

phenyllithium

1-iodo-4-phenylcubane
124225-33-8

1-iodo-4-phenylcubane

Conditions
ConditionsYield
In diethyl ether; cyclohexane for 1h; Ambient temperature;100%
In diethyl ether; pentane for 0.666667h; Ambient temperature;88%
In diethyl ether Ambient temperature;
dodec-1-en-2-yl triflate
103885-03-6

dodec-1-en-2-yl triflate

phenyllithium
591-51-5

phenyllithium

1-methyleneundecylbenzene
115146-99-1

1-methyleneundecylbenzene

Conditions
ConditionsYield
With manganese chloride bis(lithium chloride) In tetrahydrofuran; diethyl ether at 25℃; for 1h;100%
2,2,5,5-Tetramethyl-3,6-diphenyl-2,5-dihydro-pyrazine 1,4-dioxide
132402-19-8

2,2,5,5-Tetramethyl-3,6-diphenyl-2,5-dihydro-pyrazine 1,4-dioxide

phenyllithium
591-51-5

phenyllithium

1,4-dihydroxy-3,3,6,6-tetramethyl-2,2,5,5-tetraphenyl-piperazine

1,4-dihydroxy-3,3,6,6-tetramethyl-2,2,5,5-tetraphenyl-piperazine

Conditions
ConditionsYield
at 20℃; for 3h;100%
at 20℃; for 3h; PhLi excess; Yield given;
C26H24O2S
136964-79-9

C26H24O2S

phenyllithium
591-51-5

phenyllithium

C28H20
99222-19-2

C28H20

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
trans-1-iodo-2-isothiocyanatocyclohexane
60211-89-4, 63616-13-7, 93424-19-2

trans-1-iodo-2-isothiocyanatocyclohexane

phenyllithium
591-51-5

phenyllithium

N-(trans-2-iodocyclohexyl)thiobenzamide
77469-36-4

N-(trans-2-iodocyclohexyl)thiobenzamide

Conditions
ConditionsYield
In diethyl ether at -78℃; for 0.416667h;100%
2-(dimethoxymethyl)-1-naphthaldehyde
103668-60-6

2-(dimethoxymethyl)-1-naphthaldehyde

phenyllithium
591-51-5

phenyllithium

2-(dimethoxymethyl)-α-phenyl-1-naphthalenemethanol
114469-02-2

2-(dimethoxymethyl)-α-phenyl-1-naphthalenemethanol

Conditions
ConditionsYield
In diethyl ether; hexane at -78 - 0℃; for 3.25h;100%
phenyllithium
591-51-5

phenyllithium

3-Methyl-1-oxa-5-sila-spiro[4.4]nonane
139017-06-4

3-Methyl-1-oxa-5-sila-spiro[4.4]nonane

2-Methyl-3-(1-phenyl-silolan-1-yl)-propan-1-ol
139017-23-5

2-Methyl-3-(1-phenyl-silolan-1-yl)-propan-1-ol

Conditions
ConditionsYield
In diethyl ether; cyclohexane for 1h; Ambient temperature;100%
phenyllithium
591-51-5

phenyllithium

(1S*,2R*,7S*,8R*,11S*)-11-Carbomethoxy-3,3-dimethyltricyclo<5.3.1.02,8>undecane
144534-06-5

(1S*,2R*,7S*,8R*,11S*)-11-Carbomethoxy-3,3-dimethyltricyclo<5.3.1.02,8>undecane

(1S*,2R*,7S*,8R*,11S*)-3,3-Dimethyl-11-(diphenylhydroxymethyl)-tricyclo<5.3.1.02,8>undecane
144534-08-7

(1S*,2R*,7S*,8R*,11S*)-3,3-Dimethyl-11-(diphenylhydroxymethyl)-tricyclo<5.3.1.02,8>undecane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether 1) rt, 1.5 h, 2) reflux, 3 h;100%
phenyllithium
591-51-5

phenyllithium

(4S)-3-benzyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester
157823-76-2

(4S)-3-benzyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester

(S)-4-Benzoyl-3-benzyl-oxazolidin-2-one
157823-78-4

(S)-4-Benzoyl-3-benzyl-oxazolidin-2-one

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;100%
phenyllithium
591-51-5

phenyllithium

4,4-dimethyl-2,5-diphenyl-4H-imidazole 1-oxide
38870-61-0

4,4-dimethyl-2,5-diphenyl-4H-imidazole 1-oxide

1-hydroxy-2,5,5-triphenyl-4,4-dimethyl-2-imidazoline
155126-64-0

1-hydroxy-2,5,5-triphenyl-4,4-dimethyl-2-imidazoline

Conditions
ConditionsYield
In diethyl ether for 0.25h;100%
In diethyl ether for 0.25h; Yield given;
phenyllithium
591-51-5

phenyllithium

bromoacetaldehyde
17157-48-1

bromoacetaldehyde

2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

Conditions
ConditionsYield
at -78℃; for 0.25h;100%
phenyllithium
591-51-5

phenyllithium

5-Phenyl-dibenzoselenophenium; bromide

5-Phenyl-dibenzoselenophenium; bromide

phenyl o-terphenyl selenide
136004-59-6

phenyl o-terphenyl selenide

Conditions
ConditionsYield
Mechanism; 1.) THF, cyclohexane, ether, -78 deg C, 2.) THF, cyclohexane, ether, room temp.;100%
phenyllithium
591-51-5

phenyllithium

(2S)-5-oxo-1-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
185121-30-6

(2S)-5-oxo-1-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

(5S)-5-benzoyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one

(5S)-5-benzoyl-1-(9'-phenylfluoren-9'-yl)pyrrolidin-2-one

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h;100%
phenyllithium
591-51-5

phenyllithium

diphenyl(phenylethynyl)selenium trifluoromethanesulfonate

diphenyl(phenylethynyl)selenium trifluoromethanesulfonate

A

1,4-diphenyl-1,3-butadiyne
886-66-8

1,4-diphenyl-1,3-butadiyne

B

diphenylselenide
1132-39-4

diphenylselenide

C

2-(phenylethynyl)-1,1'-biphenyl
10271-65-5

2-(phenylethynyl)-1,1'-biphenyl

D

phenylacetylene
536-74-3

phenylacetylene

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 3h; Substitution; Further byproducts given;A 2%
B 100%
C 4%
D 60%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

phenyllithium
591-51-5

phenyllithium

isopropyl bromide
75-26-3

isopropyl bromide

(+/-)-4-methyl-1,3-diphenylpentan-1-one
85267-90-9

(+/-)-4-methyl-1,3-diphenylpentan-1-one

Conditions
ConditionsYield
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h;
Stage #2: isopropyl bromide In tetrahydrofuran Further stages.;
100%
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h; Addition;
Stage #2: isopropyl bromide In tetrahydrofuran at 20℃; Alkylation;
100 % Chromat.
2,3,7,8,12,13,17,18-octaethyl-porphyrin
2683-82-1

2,3,7,8,12,13,17,18-octaethyl-porphyrin

phenyllithium
591-51-5

phenyllithium

2,3,7,8,12,13,17,18-octaethyl-5-phenylporphyrine
60188-33-2

2,3,7,8,12,13,17,18-octaethyl-5-phenylporphyrine

Conditions
ConditionsYield
Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; phenyllithium In tetrahydrofuran; cyclohexane at 40℃; for 0.25h; Addition;
Stage #2: With water In tetrahydrofuran; cyclohexane Hydrolysis;
Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dichloromethane; cyclohexane for 0.0833333h; Oxidation; Further stages.;
100%
Stage #1: 2,3,7,8,12,13,17,18-octaethyl-porphyrin; phenyllithium In tetrahydrofuran at -40 - 20℃;
Stage #2: With water In tetrahydrofuran
Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Further stages.;
100%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

[(E)-2-bromoethenyl]benzene
588-72-7

[(E)-2-bromoethenyl]benzene

phenyllithium
591-51-5

phenyllithium

trans-1,3,5-triphenylpent-4-en-1-one
251635-75-3

trans-1,3,5-triphenylpent-4-en-1-one

Conditions
ConditionsYield
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h;
Stage #2: [(E)-2-bromoethenyl]benzene In tetrahydrofuran Further stages.;
100%
(1E,2E)-N,3-diphenylprop-2-en-1-imine
953-21-9

(1E,2E)-N,3-diphenylprop-2-en-1-imine

phenyllithium
591-51-5

phenyllithium

(E)-N-(1,3-diphenylallyl)aniline

(E)-N-(1,3-diphenylallyl)aniline

Conditions
ConditionsYield
Stage #1: (1E,2E)-N,3-diphenylprop-2-en-1-imine; phenyllithium In tetrahydrofuran; diethyl ether at -78℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
100%
Stage #1: (1E,2E)-N,3-diphenylprop-2-en-1-imine; phenyllithium In tetrahydrofuran at -45℃; for 1h;
Stage #2: With oxonium In tetrahydrofuran Further stages.;
92%
bicyclo<5.3.0>-dec-1(10)-en-9-one
61154-46-9

bicyclo<5.3.0>-dec-1(10)-en-9-one

phenyllithium
591-51-5

phenyllithium

2-phenyl-1,2,4,5,6,7,8,8a-octahydroazulen-2-ol
536976-48-4

2-phenyl-1,2,4,5,6,7,8,8a-octahydroazulen-2-ol

Conditions
ConditionsYield
In diethyl ether; cyclohexane at 0 - 20℃; for 2h;100%
phenyllithium
591-51-5

phenyllithium

1,4,5,6,7,8,9,9a-octahydro-2H-cyclopenta[8]annulen-2-one
225650-45-3

1,4,5,6,7,8,9,9a-octahydro-2H-cyclopenta[8]annulen-2-one

2-phenyl-2,4,5,6,7,8,9,9a-octahydro-1H-cyclopenta[8]annulen-2-ol
536976-49-5

2-phenyl-2,4,5,6,7,8,9,9a-octahydro-1H-cyclopenta[8]annulen-2-ol

Conditions
ConditionsYield
In diethyl ether; cyclohexane at 0 - 20℃; for 2h;100%
2-(methylsulfanyl)pyrimidine
823-09-6

2-(methylsulfanyl)pyrimidine

phenyllithium
591-51-5

phenyllithium

2-(methylsulfanyl)-4-phenylpyrimidine
56734-10-2

2-(methylsulfanyl)-4-phenylpyrimidine

Conditions
ConditionsYield
Stage #1: 2-(methylsulfanyl)pyrimidine; phenyllithium In tetrahydrofuran at 0℃; for 2h;
Stage #2: With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 0.75h;
100%
2-(methylsulfanyl)-4-phenylpyrimidine
56734-10-2

2-(methylsulfanyl)-4-phenylpyrimidine

phenyllithium
591-51-5

phenyllithium

2-(methylsulfanyl)-4,6-diphenylpyrimidine
59807-21-5

2-(methylsulfanyl)-4,6-diphenylpyrimidine

Conditions
ConditionsYield
Stage #1: 2-(methylsulfanyl)-4-phenylpyrimidine; phenyllithium In tetrahydrofuran at 20℃; for 4h;
Stage #2: With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 0.75h;
100%
1-Bromoanthraquinone
632-83-7

1-Bromoanthraquinone

phenyllithium
591-51-5

phenyllithium

1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol
955123-64-5

1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol

Conditions
ConditionsYield
In tetrahydrofuran; dibutyl ether at 20℃; for 24h;100%

PHENYLLITHIUM Chemical Properties

Molecular Formula: C6H5Li
Molecular Weight: 84.04
EINECS: 209-720-1
Flash point: 20 ºC
Storage temp:  2-8°C
Boiling point: 140-143 º  C
Density: 0.835 g/mL at 25 °C
Water solubility: vigorous reaction
Sensitive of Phenyllithium (591-51-5): Air & Moisture Sensitive 
Synonyms: Lithiumphenyl;Phenyl-lithiu;Phenyllithium;Phenyllithium dibutyl;Phli;Phenyllithium, 1.9m solution in cyclo-hexane-ether, 70 to 30;Phenyllithium solution 20% in dibutylether;Phenyllithium sol., 1.8-2.1 m in cyclo- hexane/ether 70/30%
Product Categories: Classes of Metal Compounds;Li (Lithium) Compounds;Typical Metal Compounds
Following is the molecular structure of Phenyllithium (591-51-5):


 

PHENYLLITHIUM Safety Profile

Incompatible with air, water. Product of reaction with titanium tetraethoxide ignites spontaneously in air and reacts violently with water. When heated to decomposition it emits toxic fumes of Li2O.
Safety Information of Phenyllithium (591-51-5):
Hazard Codes  F,C,N
F: Highly Flammable  C: Corrosive  N: Dangerous for the environment
Risk Statements: 11-14-17-34-52/53-67-66-65-50/53-22-19-35
11: Highly Flammable 
14: Reacts violently with water 
17: Spontaneously flammable in air 
34: Causes burns 
52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
67: Vapors may cause drowsiness and dizziness 
66: Repeated exposure may cause skin dryness or cracking 
65: Harmful: May cause lung damage if swallowed 
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
22: Harmful if swallowed 
19: May form explosive peroxides 
35: Causes severe burns 
Safety Statements: 26-36/37/39-45-61-62-60-43-16-6-8
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
61: Avoid release to the environment. Refer to special instructions safety data sheet 
62: If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label
60: This material and/or its container must be disposed of as hazardous waste 
43: In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water) 
16: Keep away from sources of ignition - No smoking 
6: Keep under ... (inert gas to be specified by the manufacturer) 
8: Keep container dry 
RIDADR: UN 3392 4.2/PG 1
WGK Germany: 2
HazardClass: 4.3
PackingGroup: II

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