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Phenyllithium
Cas No: 591-51-5
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Phenyllithium
Cas No: 591-51-5
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Factory Supply Phenyllithium
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PhenyllithiumCAS NO.:591-51-5
Cas No: 591-51-5
USD $ 4.0-4.0 / Gram 1 Gram 11000 Gram/Day Henan Wentao Chemical Product Co., Ltd. Contact Supplier
Pharmaceutical Grade CAS 591-51-5 with competitive price
Cas No: 591-51-5
USD $ 139.0-210.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Zhuozhou Wenxi import and Export Co., Ltd Contact Supplier
Phenyl lithium
Cas No: 591-51-5
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
Lithium, phenyl-
Cas No: 591-51-5
No Data 1 Gram 10000 Metric Ton/Month Shanghai Upbio Tech Co.,Ltd Contact Supplier
Phenyllithium 99%
Cas No: 591-51-5
USD $ 84.0-98.0 / Kilogram 1 Kilogram 100 Metric Ton/Month Baoji Guokang Healthchem co.,ltd Contact Supplier
Lithium, phenyl-
Cas No: 591-51-5
No Data 1 Kilogram 1 Metric Ton/Day Shandong Hanjiang Chemical Co., Ltd. Contact Supplier
LITHIUMPHENYL
Cas No: 591-51-5
No Data 1 Gram Metric Ton/Day Afine Chemicals Limited Contact Supplier

591-51-5 Usage

Description

Phenyllithium is an organometallic compound that is used as a nucleophile for substitution and addition reactions, and in the synthesis of organolithium building blocks through lithium-metalloid and metalation exchange reactions.

Properties

Phenyllithium has a molecular weight of 84.046 g/mol, a monoisotopic mass of 84.055 g/mol and an exact mass of 84.055 g/mol. It has a heavy atom count of 7 and a complexity of 95.8. Phenyllithium is soluble in ether solvents; it is soluble in hydrocarbon solvents especially through the addition of donor additives/solvents.

Uses

Phenyllithium is used for synthetic purposes to introduce a phenyl group into a compound or for metalation reactions. It undergoes typical Grignard type reactions.

Preparation

Phenyllithium is synthesized by reacting elemental lithium with bromobenzene and dissolving the resulting products in ether. 18g[2.57 mol] of lithium that contains about 1-3% of sodium is flattened out using a hammer to attain a thickness of about 1.5 mm and then it is cut into chips of about 2x10x1.5 mm. The chips are placed into a flask holding 800 ml of anhydrous diethyl ether. The air is purged with dry argon or dry nitrogen and the ether is condensed to -250 C in the first two minutes of the reaction. 150.7 g of bromobenzene is placed into the flask through the dropping funnel, where one portion contains only 10 g of bromobenzene. After a few minutes of the reaction, there is a significant rise in temperature and the contents of the flask appear turbid. When the reaction starts to subside, after about 10 minutes, the remaining bromobenzene is added gradually to the flask using a dropper over a period of 1 hour, while maintaining the temperature of the contents between -150 C and -200 C. The dark coating on the lithium metal subsides almost entirely leaving behind a silver-like appearance. Once all the bromobenzene is added to the flask, the contents are stirred and the temperature is maintained at -150 C for 1 hour. The temperature should then be allowed to increase up to 00, which will also be indicated a gradually fading glow of the reacting metal. The resulting solution is emptied into a storage flask that has been filled with an inert gas. The filtration of the solution should take place in an inert atmosphere where a steady stream of argon or nitrogen[2-3 l/min] is passed through the reaction contents to prevent the solution from oxidation. Diethyl ether is then added to increase the Volume of the solution to 1 litre. The contents of the flask are then swirled gently[homogenization] to allow for the final step of the reaction, where the concentration is determined. Solutions containing Phenyllithium are unstable at room temperature when left for long periods of time. The gradual attack of Phenyllithium on ethyl ether makes the commercial preparation of the compound undesirable. The incorporation of small quantities of ethyl ether to attain solutions of 1:1 phenyllithiumzethyl etherate complex in the presence of benzene reduces the average titer of the ethyl ether hence it makes the solution more stable. The average titer should be about 1 molar, which corresponds to a high yield[90%] and purity. Amounts that are significantly higher or lower than the mol ratio often yield lesser amounts of Phenyllithium. The resulting 1:1 phenyllithiumzethyl etherate complex could be a tetramer or a dimer but it does not affect the ethyl ether to Phenyllithium ratio, which remains 1:1.

Application

Phenyllithium can be used in the preparation of 1-Acetyl-1′-diphenylphosphinoferrocene from ferrocenophane

Hazard Statements

Phenyllithium is a flammable liquid/vapour and it may catch fire when exposed to air. When it comes into contact with water it emits flammable gases. Phenyllithium may result in acute toxicity upon ingestion and inhalation, or when it comes into contact with one’s eyes and skin.

Chemical Properties

Phenyllithium is a colorless crystalline solid or dark brown to black solution, It is soluble in polar solvents such as ethers and tertiary amines but insoluble in hydrocarbons. Concentrated solutions in volatile solvents are pyrophoric but can be safely handled under inert atmosphere.

Uses

Phenyllithium Solution (1.9M in Dibutyl Ether) is used as catalyst in the synthesis of pharmaceuticals. Used in the preparation of sulfonamides as well as in the preparation of orally bioavailable inhibitors of lipoprotein-associated phospholipase A2.

Preparation

Phenyllithium is usually prepared in the laboratory from bromobenzene and lithium metal in diethyl ether. Since phenyllithium cleaves ether, the solution must be used within a day or refrigerated. Industrially, it is produced from chlorobenzene and lithium metal dispersion in a benzene-ether mixture. A potentially useful and inexpensive process is one in which benzene is metalated by n-butyllithium in the presence of di-tertiary amines.
InChI:InChI=1/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H;/rC6H5Li/c7-6-4-2-1-3-5-6/h1-5H

591-51-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (45770)  Phenyllithium, typically 1.9M in di-n-butyl ether    591-51-5 25ml 312.0CNY Detail
Alfa Aesar (45770)  Phenyllithium, typically 1.9M in di-n-butyl ether    591-51-5 100ml 838.0CNY Detail
Alfa Aesar (45770)  Phenyllithium, typically 1.9M in di-n-butyl ether    591-51-5 *5x100ml 3562.0CNY Detail

591-51-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name phenyllithium

1.2 Other means of identification

Product number -
Other names PHENYLLITHIUM SOLUTION IN DIBUTYLETHER

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:591-51-5 SDS

591-51-5Synthetic 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%
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