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; |
N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole
tert-butylamine
phenyllithium
Conditions | Yield |
---|---|
In benzene at 80℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; | 84% |
Conditions | Yield |
---|---|
With lithium In diethyl ether Inert atmosphere; Schlenk technique; | 74% |
With lithium; benzene |
Conditions | Yield |
---|---|
In diethyl ether 20°C; | A n/a B 22% |
n-butyllithium
bromobenzene
diethyl ether
phenyllithium
n-butyllithium
diethyl ether
hexaphenyl diplumbane
A
hexabutyldiplumbum
B
phenyllithium
n-butyllithium
diethyl ether
diphenylmagnesium
A
dibutylmagnesium
B
phenyllithium
Conditions | Yield |
---|---|
reversible Reaktion; |
n-butyllithium
diphenylselenide
A
butyl phenyl selenide
B
Benzeneselenol
C
phenyllithium
Conditions | Yield |
---|---|
analoge Umsetzungen erfolgen mit Tetrakis-<4-chlor-phenyl>-zinn und mit Dibenzylquecksilber; |
Conditions | Yield |
---|---|
With benzene |
ethyllithium
diphenylmercury(II)
A
diethylmercury
B
phenyllithium
n-butyllithium
diethyl ether
tetraphenyltin(IV)
benzene
A
tetra-n-butyltin(IV)
B
phenyllithium
Conditions | Yield |
---|---|
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
diethyl ether
Tetraphenyllead
benzene
A
tetra-n-butyl lead
B
phenyllithium
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
A
phenyllithium
B
1,3-bis(lithiumphenylphosphido)propane
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran |
1,5-bis-(diphenylphosphino)pentane
A
phenyllithium
B
1,5-Bis--pentamethylen
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran |
Conditions | Yield |
---|---|
With 1-iodo-butane In tetrahydrofuran at -78℃; Equilibrium constant; solvent effect; |
bicyclo<1.1.1>pentyl phenyl sulfide
A
lithium thiophenoxide
B
C5H7Li
C
Lithium; bicyclo[1.1.1]pentane-1-thiolate
D
phenyllithium
Conditions | Yield |
---|---|
With 4,4'-di-tert-butylbiphenyl; lithium at -60℃; |
1,2-diphenyl-3,4-di-t-butyldiphosphete
A
phenyllithium
B
(2-phenyl-3,4-di-tert-butyl-1,2-diphosphetenyl)lithium
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran Product distribution; Ambient temperature; |
Conditions | Yield |
---|---|
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
A
phenyllithium
B
1,4-Bis--tetramethylen
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran |
n-butyllithium
diphenylmercury(II)
benzene
phenyllithium
n-butyllithium
diethyl ether
A
4-chlorophenyl lithium
B
phenyllithium
n-butyllithium
diethyl ether
A
4-chlorophenyl lithium
B
phenyllithium
Conditions | Yield |
---|---|
mit Dibenzylquecksilber erfolgt eine analoge Umsetzung; |
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran at -30℃; for 0.583333h; lithiation; |
Conditions | Yield |
---|---|
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
3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine
3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1,4-dihydro-4-phenylpyridine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In diethyl ether; benzene at -78℃; | 100% |
(E)-3-phenylpropenal
chloro-trimethyl-silane
phenyllithium
(E)-1,3-diphenyl-1-trimethylsilyloxy-2-propene
Conditions | Yield |
---|---|
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
phenyllithium
(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose
Conditions | Yield |
---|---|
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
phenyllithium
2-phenyl-2,4,5,6,7,7a-hexahydro-1H-inden-2-ol
Conditions | Yield |
---|---|
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
phenyllithium
2-tert-Butylperoxy-2-methyl-1-phenyl-cyclohexanol
Conditions | Yield |
---|---|
In diethyl ether at -78℃; for 0.666667h; | 100% |
Conditions | Yield |
---|---|
In diethyl ether; cyclohexane for 1h; Ambient temperature; | 100% |
In diethyl ether; pentane for 0.666667h; Ambient temperature; | 88% |
In diethyl ether Ambient temperature; |
Conditions | Yield |
---|---|
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
phenyllithium
Conditions | Yield |
---|---|
at 20℃; for 3h; | 100% |
at 20℃; for 3h; PhLi excess; Yield given; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; | 100% |
trans-1-iodo-2-isothiocyanatocyclohexane
phenyllithium
N-(trans-2-iodocyclohexyl)thiobenzamide
Conditions | Yield |
---|---|
In diethyl ether at -78℃; for 0.416667h; | 100% |
2-(dimethoxymethyl)-1-naphthaldehyde
phenyllithium
2-(dimethoxymethyl)-α-phenyl-1-naphthalenemethanol
Conditions | Yield |
---|---|
In diethyl ether; hexane at -78 - 0℃; for 3.25h; | 100% |
phenyllithium
3-Methyl-1-oxa-5-sila-spiro[4.4]nonane
2-Methyl-3-(1-phenyl-silolan-1-yl)-propan-1-ol
Conditions | Yield |
---|---|
In diethyl ether; cyclohexane for 1h; Ambient temperature; | 100% |
phenyllithium
(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
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether 1) rt, 1.5 h, 2) reflux, 3 h; | 100% |
phenyllithium
(4S)-3-benzyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester
(S)-4-Benzoyl-3-benzyl-oxazolidin-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.5h; | 100% |
phenyllithium
4,4-dimethyl-2,5-diphenyl-4H-imidazole 1-oxide
1-hydroxy-2,5,5-triphenyl-4,4-dimethyl-2-imidazoline
Conditions | Yield |
---|---|
In diethyl ether for 0.25h; | 100% |
In diethyl ether for 0.25h; Yield given; |
Conditions | Yield |
---|---|
at -78℃; for 0.25h; | 100% |
phenyllithium
phenyl o-terphenyl selenide
Conditions | Yield |
---|---|
Mechanism; 1.) THF, cyclohexane, ether, -78 deg C, 2.) THF, cyclohexane, ether, room temp.; | 100% |
phenyllithium
(2S)-5-oxo-1-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 1h; | 100% |
phenyllithium
A
1,4-diphenyl-1,3-butadiyne
B
diphenylselenide
C
2-(phenylethynyl)-1,1'-biphenyl
D
phenylacetylene
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 3h; Substitution; Further byproducts given; | A 2% B 100% C 4% D 60% |
(E)-3-phenylpropenal
phenyllithium
isopropyl bromide
(+/-)-4-methyl-1,3-diphenylpentan-1-one
Conditions | Yield |
---|---|
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
phenyllithium
2,3,7,8,12,13,17,18-octaethyl-5-phenylporphyrine
Conditions | Yield |
---|---|
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
[(E)-2-bromoethenyl]benzene
phenyllithium
trans-1,3,5-triphenylpent-4-en-1-one
Conditions | Yield |
---|---|
Stage #1: (E)-3-phenylpropenal; phenyllithium In tetrahydrofuran at 20℃; for 7h; Stage #2: [(E)-2-bromoethenyl]benzene In tetrahydrofuran Further stages.; | 100% |
Conditions | Yield |
---|---|
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
phenyllithium
2-phenyl-1,2,4,5,6,7,8,8a-octahydroazulen-2-ol
Conditions | Yield |
---|---|
In diethyl ether; cyclohexane at 0 - 20℃; for 2h; | 100% |
phenyllithium
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
Conditions | Yield |
---|---|
In diethyl ether; cyclohexane at 0 - 20℃; for 2h; | 100% |
2-(methylsulfanyl)pyrimidine
phenyllithium
2-(methylsulfanyl)-4-phenylpyrimidine
Conditions | Yield |
---|---|
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
phenyllithium
2-(methylsulfanyl)-4,6-diphenylpyrimidine
Conditions | Yield |
---|---|
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
phenyllithium
1-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol
Conditions | Yield |
---|---|
In tetrahydrofuran; dibutyl ether at 20℃; for 24h; | 100% |
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):
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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