METHYLLITHIUM supplier | CasNO.917-54-4

Name
METHYLLITHIUM
EINECS 213-026-4
CAS No. 917-54-4
Article Data43
CAS DataBase
Density 0.85 g/mL at 20 °C
Solubility Reacts with water.
Melting Point 70-71oC
Formula CH₃Li
Boiling Point 35oC
Molecular Weight 21.9758
Flash Point 5°F
Transport Information UN 3399 4.3/PG 1
Appearance colorless to yellowish solution
Safety 16-26-36/37/39-45-43-30-60
Risk Codes 12-15-17-22-34-66-67-65-51/53-11
Molecular Structure
Hazard Symbols F+,C,N,F
Synonyms Lithiummethide;
PSA 0.00000
LogP 0.58380

Synthetic route

: 74-83-9
methyl bromide

: 7439-93-2
lithium

: 917-54-4
methyllithium

Conditions

Conditions	Yield
In formaldehyde diethyl acetal at 10 - 30℃; for 2.5 - 7.5h;	91%
reaction at -40°C;;

: 65457-77-4
4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone

A: 917-54-4
methyllithium

: 99474-57-4, 99474-58-5, 114790-76-0
(1S,4S)-1-Methyl-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enol

Conditions

Conditions	Yield
In tetrahydrofuran at -30℃; for 1h;	A 86% B 6%

: 74-88-4
methyl iodide

: 917-54-4
methyllithium

Conditions

Conditions	Yield
With n-butyllithium In hexane; dichloromethane at -40 - 20℃; for 1h; Inert atmosphere;	83%
With diethyl ether; lithium
With lithium

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

: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

A: 917-54-4
methyllithium

B: 75934-66-6
pentamethylpentylbenzene

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In Cyclopentane at 55℃; for 5.5h;	A n/a B 77%

...Expand

: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

: 594-19-4
tert.-butyl lithium

A: 917-54-4
methyllithium

B: 56909-25-2
2,3,4,5,6-pentamethylneopentylbenzene

Conditions

Conditions	Yield
In cyclohexane at 88℃; for 3.3h;	A n/a B 63%

...Expand

: 74-83-9
methyl bromide

: 917-54-4
methyllithium

Conditions

Conditions	Yield
With lithium

: 74-87-3
methylene chloride

: 917-54-4
methyllithium

Conditions

Conditions	Yield
With bromobenzene; diethyl ether; lithium
With iodobenzene; diethyl ether; lithium
With lithium

: 811-49-4
ethyllithium

: 593-74-8
dimethylmercury

: 917-54-4
methyllithium

Conditions

Conditions	Yield
With Petroleum ether

: 811-49-4
ethyllithium

: 593-74-8
dimethylmercury

A: 917-54-4
methyllithium

B: 627-44-1
diethylmercury

...Expand

: 811-49-4
ethyllithium

: 74-88-4
methyl iodide

: 917-54-4
methyllithium

: 83781-00-4
(1S,5S,7R)-7-Bromomethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

A: 917-54-4
methyllithium

B: 64313-75-3
(1S,7S)-exo-brevicomin

Conditions

Conditions	Yield
With copper(l) iodide 1.) ether, 10 deg C, 10 min, 2.) HMPA, RT, 24 h; Yield given. Multistep reaction. Title compound not separated from byproducts;

: 75-16-1
methylmagnesium bromide

: 115378-72-8
(2R,5R)-N-benzoylcarbonyl-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

A: 917-54-4
methyllithium

B: 126884-67-1
(R)-1-((2R,5R)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2-hydroxy-2-phenyl-propan-1-one

Conditions

Conditions	Yield
In tetrahydrofuran at -80 - 35℃; Product distribution; effect of temperature and solvent on diastereomeric excess;

...Expand

: 75961-61-4
C17H29Li

A: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B: 917-54-4
methyllithium

C: 75934-67-7
(β-methylbutyl)-pentamethylbenzene

D: 75948-86-6
(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,4-cyclohexadiene

E: 75948-82-2
(β-methylbutyl)-1,1,2,3,5,6-hexamethyl-2,5-cyclohexadiene

Conditions

Conditions	Yield
With 1-Methylpyrrolidine; hydrogenchloride In Cyclopentane Product distribution;	A 9 % Chromat. B n/a C 1 % Chromat. D 38 % Chromat. E 52 % Chromat.

...Expand

: 75961-61-4
C17H29Li

A: 917-54-4
methyllithium

B: 75934-67-7
(β-methylbutyl)-pentamethylbenzene

Conditions

Conditions	Yield
In Cyclopentane at 20℃; Kinetics;

: 75961-59-0
1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium

A: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B: 917-54-4
methyllithium

C: 75934-66-6
pentamethylpentylbenzene

D: 75948-83-3
1,1,2,3,5,6-hexamethyl-4-pentyl-2,5-cyclohexadiene

E: 75948-79-7
1,1,2,3,5,6-hexamethyl-4-pentyl-2,4-cyclohexadiene

Conditions

Conditions	Yield
With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine In Cyclopentane Product distribution;	A 0.7 % Chromat. B n/a C 2 % Chromat. D 41.0 % Chromat. E 56.0 % Chromat.

...Expand

: 75961-59-0
1,1,2,3,5,6-hexamethyl-4-pentylcyclohexadienyllithium

A: 917-54-4
methyllithium

B: 75934-66-6
pentamethylpentylbenzene

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In Cyclopentane at 20℃; Kinetics;
With 1-Methylpyrrolidine In Cyclopentane at 20℃; Kinetics;
With tetrahydrofuran In Cyclopentane at 20℃; Kinetics;

: 79376-82-2
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B: 917-54-4
methyllithium

C: 56909-25-2
2,3,4,5,6-pentamethylneopentylbenzene

D: 75948-84-4
1,1,2,3,5,6-hexamethyl-4-neopentyl-2,4-cyclohexadiene

E: 75948-80-0
1,1,2,3,5,6-hexamethyl-4-neopentyl-2,5-cyclohexadiene

Conditions

Conditions	Yield
With tetrahydrofuran; hydrogenchloride In Cyclopentane Product distribution;	A 5 % Chromat. B n/a C 9 % Chromat. D 33 % Chromat. E 54 % Chromat.

...Expand

: 79376-82-2
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A: 3043-52-5
1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene

B: 917-54-4
methyllithium

C: 56909-25-2
2,3,4,5,6-pentamethylneopentylbenzene

D: 75948-85-5
C17H29(2)H

E: 75948-81-1
C17H29(2)H

Conditions

Conditions	Yield
With 1-Methylpyrrolidine; water-d2 In Cyclopentane Product distribution;	A 0.1 % Chromat. B n/a C 0.1 % Chromat. D n/a E n/a

...Expand

: 79376-82-2
1,1,2,3,5,6-hexamethyl-4-neopentylcyclohexadienyllithium

A: 917-54-4
methyllithium

B: 56909-25-2
2,3,4,5,6-pentamethylneopentylbenzene

Conditions

Conditions	Yield
In Cyclopentane at 20℃; Kinetics;
In Cyclopentane at 25℃; Kinetics;
With 1-Methylpyrrolidine In Cyclopentane at 20℃; Kinetics;
With tetrahydrofuran In Cyclopentane at 20℃; Kinetics;

: 95122-04-6
(2S,3aR,5aR,8aR)-3a,5,5-Trimethyl-6-oxo-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalene-2-carboxylic acid

A: 917-54-4
methyllithium

: 95122-06-8
6,6,8-trimethyltricyclo<6.3.0.01,5>undeca-2,9-dien-4-one

Conditions

Conditions	Yield
With lead(IV) acetate; copper diacetate In pyridine 3 h, dark; ref., 1 h; Yield given. Yields of byproduct given;

: 72170-87-7
(+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine

: 80-48-8
methyl p-toluene sulfonate

A: 917-54-4
methyllithium

B: 62392-84-1
(+)-(R)-6-methylcyclohex-2-en-1-one

Conditions

Conditions	Yield
With hydrogenchloride; PriNLi; methyl iodide 1.) THF, -20 deg C; 2.) pentane; Multistep reaction;

...Expand

: C15H17Si(1-)*4C4H8O*Li(1+)

A: 13688-68-1
9,9-dimethyl-9-silafluorene

B: 917-54-4
methyllithium

Conditions

Conditions	Yield
Heating;

: 811-49-4
ethyllithium

: 593-74-8
dimethylmercury

petroleum ether: petroleum ether

A: 917-54-4
methyllithium

B: 627-44-1
diethylmercury

...Expand

: 578-58-5
2-methylmethoxybenzene

A: 917-54-4
methyllithium

B: 83859-26-1
lithium 2-methylphenolate

C: 6-lithio-2-methyl anisole

Conditions

Conditions	Yield
With lithium In tetrahydrofuran at -196.15℃;

...Expand

: 1004-66-6
2-methoxy-1,3-dimethylbenzene

A: 917-54-4
methyllithium

B: 24560-29-0
lithium 2,6-dimethylphenolate dimer

C: 4-lithio-2,6-dimethyl anisole

Conditions

Conditions	Yield
With lithium In tetrahydrofuran at -196.15℃;

...Expand

: 7439-93-2
lithium

: 74-88-4
methyl iodide

: 917-54-4
methyllithium

: 593-74-8
dimethylmercury

: 7439-93-2
lithium

: 917-54-4
methyllithium

Conditions

Conditions	Yield
In not given

: 75764-11-3
bis(pentamethylcyclopentadienyl)ytterbium

: lithium iodide

: 917-54-4
methyllithium

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

: 1527-99-7
n-butyltrimethyltin

A: 917-54-4
methyllithium

B: 1528-00-3
di-n-butyldimethylstannane

Conditions

Conditions	Yield
In tetrahydrofuran-d8 NMR-tube; molar ratio 1:1, 1:2 and excess LiBu at -60 °C and room temp.; (1)H-NMR at -60 °C and room temp.;

...Expand

: 917-54-4
methyllithium

: 826-35-7
dimethyl trans-1,2-cyclopropanedicarboxylate

: 3193-89-3, 7731-99-9, 91367-51-0, 123886-35-1
trans-α,α,α',α'-tetramethylcyclopropane-1,2-diyldimethanol

Conditions

Conditions	Yield
In diethyl ether for 2h;	100%
In diethyl ether; hexane

: 917-54-4
methyllithium

: 502-42-1
cycloheptanone

: 3761-94-2
1-methylcycloheptanol

Conditions

Conditions	Yield
In diethyl ether at -78℃;	100%

: 917-54-4
methyllithium

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

: 68981-79-3
3-(4,4-dimethyloxazolin-2-yl)-4-methyl-1,4-dihydropyridine

Conditions

Conditions	Yield
In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) 0 deg C, 1 h;	100%
In diethyl ether for 1h; Ambient temperature;	69.3%

: 930-68-7
cyclohexenone

: 917-54-4
methyllithium

: 23758-27-2
1-methylcyclohex-2-en-1-ol

Conditions

Conditions	Yield
Stage #1: cyclohexenone; methyllithium With lithium bromide In 2-methyltetrahydrofuran; diethyl ether at 0℃; for 2h; Stage #2: With ammonium chloride In 2-methyltetrahydrofuran; diethyl ether; water at 0℃; regioselective reaction;	100%
Stage #1: methyllithium With cerium(III) chloride In tetrahydrofuran; diethyl ether for 0.5h; Stage #2: cyclohexenone In tetrahydrofuran; diethyl ether at -78℃; for 3h;	78%
Inert atmosphere; Cooling with ice;	67%

: 14233-64-8
tri-O-benzyl-D-arabinolactone

: 917-54-4
methyllithium

: 138811-36-6
1-methyl-2,3,5-tri-O-benzyl-D-arabinofuranose

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃; for 0.0833333h;	100%
In tetrahydrofuran; diethyl ether at -78℃; for 6h; Inert atmosphere;	86%
In tetrahydrofuran

: 55182-92-8
9-tetradecynoic acid

: 917-54-4
methyllithium

: 98321-46-1
10-pentadecyn-2-one

Conditions

Conditions	Yield
In diethyl ether for 4h; Ambient temperature;	100%

: 25462-04-8
2-Methyl-2-(tert-butylperoxy)cyclohexanon

: 917-54-4
methyllithium

: 19781-07-8
2,7-dimethyloctane-2,7-diol

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 25462-04-8
2-Methyl-2-(tert-butylperoxy)cyclohexanon

: 917-54-4
methyllithium

: 109139-10-8
2-tert-Butylperoxy-1,2-dimethyl-cyclohexanol

Conditions

Conditions	Yield
In diethyl ether at -78℃; for 0.5h;	100%

: 1149-24-2
2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester

: 917-54-4
methyllithium

: 117860-48-7
3,5-bis<2-(2-hydroxypropyl)>-2,6-lutidine

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 52190-42-8
2-phenylsulfanylcyclooctanone

: 917-54-4
methyllithium

: 101704-33-0, 125334-90-9
(1R,2R)-1-Methyl-2-phenylsulfanyl-cyclooctanol

Conditions

Conditions	Yield
	100%

: 124921-28-4
1-benzyl-1-cyano-5-methoxy-1,2,3,4-tetrahydronaphthalene

: 917-54-4
methyllithium

: 124921-43-3
1-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃;	100%

: 115878-31-4, 125133-34-8
(10S*,11R*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5H-dibenzocyclohepten-5-one

: 917-54-4
methyllithium

: 125025-42-5, 125134-16-9
(10S*,11S*)-11-(tert-butylcarboxamido)-10,11-dihydro-10-hydroxy-5-methyl-5H-dibenzocycloheptene

Conditions

Conditions	Yield
In tetrahydrofuran at -5℃; for 2.2h;	100%

: 917-54-4
methyllithium

: 112522-04-0
(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

: 116914-45-5
(3S,6S,7aR)-6-Benzyl-3-isopropyl-6,7a-dimethyl-5-methylene-hexahydro-pyrrolo[2,1-b]oxazole

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; for 1h;	100%
In tetrahydrofuran at -78℃;	99%

: 917-54-4
methyllithium

: 100033-95-2
N-(phenylselenocarbonyl) piperidine

: 14990-66-0
1-(1-phenylvinyl)piperidine

Conditions

Conditions	Yield
In tetrahydrofuran 1) -78 deg C, 1h, 2) -78 to 0 deg C, 1h;	100%

: 917-54-4
methyllithium

: 110110-37-7
3-(1H-indol-3-yl)-acrylic acid ethyl ester

: 134051-29-9
(E)-β-(3-Hydroxy-3-methylbutenyl)indole

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether for 5h; Heating;	100%
In tetrahydrofuran Heating;

: 917-54-4
methyllithium

: 74857-26-4
(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropanecarboxylic acid ethyl ester

: 76833-07-3
2-[(1R,2R)-2-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopropyl]-propan-2-ol

Conditions

Conditions	Yield
In diethyl ether; pentane 1.) from -5 deg C to 5 deg C, 2.) room temp., 8 h;	100%

: 917-54-4
methyllithium

: 94399-73-2
anti-6-methyl-cis-1,5-dicarbomethoxybicyclo<3.3.0>octane

: 2-methylene-4,4,8-trimethyl-3-oxatricyclo<3.3.3.0>decane

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 917-54-4
methyllithium

: 85532-84-9
C14H20O4

: 85532-85-0, 85532-94-1
C15H24O4

Conditions

Conditions	Yield
	100%

: 917-54-4
methyllithium

: 94851-59-9
Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-2,5,5,8a-tetramethyl-1-(3-oxo-pent-4-enyl)-decahydro-naphthalen-2-yl ester

: 94851-60-2, 94851-63-5
Acetic acid (1S,2R,4aS,6R,8aR)-6-bromo-1-(3-hydroxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yl ester

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 15h;	100%

: 917-54-4
methyllithium

: 109271-09-2, 109271-12-7
(2Z,6E,10E)-7-Methyl-13-(2-methyl-5-oxo-cyclopent-1-enyl)-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester

: 109271-02-5, 109281-86-9
(2Z,6E,10E)-13-(5-Hydroxy-2,5-dimethyl-cyclopent-1-enyl)-7-methyl-2-triethylsilanylmethyl-trideca-2,6,10-trienoic acid isopropyl ester

Conditions

Conditions	Yield
at -78℃; 1 h. then repeat;	100%

: 4593-90-2, 772-15-6
(S)-2-phenylbutanoic acid

: 917-54-4
methyllithium

: 32587-80-7
(S)-4-phenylpentan-2-one

Conditions

Conditions	Yield
In diethyl ether at 0 - 20℃; for 2.5h;	100%
In diethyl ether for 4h; Ambient temperature;	97%
In diethyl ether at -78 - 20℃; Inert atmosphere;	82%
In diethyl ether at -78℃; for 0.5h;	54%
With copper(l) cyanide Inert atmosphere;

: 917-54-4
methyllithium

: 85428-13-3
((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-acetic acid

: 85428-20-2
1-((1R,3S)-1,3-Dimethyl-2-methylene-cyclohexyl)-propan-2-one

Conditions

Conditions	Yield
In diethyl ether 1) ice bath 2) 5h, room temperature;	100%
In diethyl ether

: 917-54-4
methyllithium

: 64937-42-4
Methyl-6-endo-(Methylthio)bicyclo<2.2.1>heptane-2-exo-carboxylate

: 91738-66-8
2-((1S,2S,4S,6S)-6-Methylsulfanyl-bicyclo[2.2.1]hept-2-yl)-propan-2-ol

Conditions

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	100%

: 917-54-4
methyllithium

: 82995-44-6
2,2,4-trimethyltricyclo<6.3.0.04,8>undec-6-en-9-one

: 86105-49-9
(3aS,5aS,8aS)-1,4,4,5a-Tetramethyl-1,2,3,3a,4,5,5a,6-octahydro-cyclopenta[c]pentalen-1-ol

Conditions

Conditions	Yield
In hexane 1.) -78 deg C, 6 h, 2.) room temperature, overnight;	100%

: 917-54-4
methyllithium

: 85428-17-7
(1aS,3aS,7R,7aS)-2-Hydroxy-3a,7-dimethyl-hexahydro-cyclopropa[c]indene-1a-carboxylic acid methyl ester

: 85428-18-8
(1aS,3aS,7R,7aS)-1a-(1-Hydroxy-1-methyl-ethyl)-3a,7-dimethyl-octahydro-cyclopropa[c]inden-2-ol

Conditions

Conditions	Yield
In diethyl ether	100%
In diethyl ether 1) ice bath 2) 1h, room temperature;	100%

: 917-54-4
methyllithium

: 124216-74-6
4-allyl-4-(3-methoxyphenyl)-1-methylpiperidin-3-one

: 124216-79-1
cis-4-allyl-4-(3-methoxyphenyl)-1,3-dimethylpiperidin-3-ol

Conditions

Conditions	Yield
In tetrahydrofuran for 0.75h; Ambient temperature;	100%

: 917-54-4
methyllithium

: 135040-39-0
8a-formyl-5,5-dimethyl-3,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone ethylene acetal

: 135040-40-3
1-(5',5'-Dimethyl-5',6',7',8'-tetrahydro-3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'a-yl)-ethanol

Conditions

Conditions	Yield
In diethyl ether at 0 - 20℃; for 4.5h;	100%

: 917-54-4
methyllithium

: 136649-78-0
3-Methyl-1-(trimethylsilyl)buta-1,2-dien-1-yl p-tolyl sulfone

: 136649-79-1
2,3-Dimethyl-1-(trimethylsilyl)but-2-en-1-yl p-tolyl sulfone

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃; for 3h;	100%
Yield given;

: 917-54-4
methyllithium

: 119327-09-2
(8aS)-1,8a-dihydro-8a-methyl-6(2H)-azulenone

: 119327-11-6, 119327-14-9
(6ξ,8aS)-1,2,6,8a-tetrahydro-6,8a-dimethyl-6-azulenol

Conditions

Conditions	Yield
In diethyl ether at -60℃; for 2.4h;	100%

: 917-54-4
methyllithium

: 76192-89-7
(3α,4α,7α,8aβ)-4,7,8a-trimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-3a,7-methanoazulene-9-one

: (3aS,4S,7R,8aR)-4,7,8a,9-Tetramethyl-octahydro-3a,7-methano-azulen-9-ol

Conditions

Conditions	Yield
In tetrahydrofuran for 3h; Heating;	100%

METHYLLITHIUM Chemical Properties

Methyllithium(917-54-4) is an organolithium reagent with the empirical formula CH₃Li and its formula weight is 21.98.
This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used as a solution in ethers, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium(917-54-4) require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium(917-54-4) is usually not prepared, but purchased as a solution in various ethers.
The density of methyllithium(917-54-4) is 0.85 g/mL at 20 °C and it has a flash point of 5 °F.
The molecular structure of methyllithium(917-54-4):

METHYLLITHIUM Production

In the direct synthesis, methyl bromide is treated with a suspension of lithium in diethyl ether.
2 Li + MeBr → LiMe + LiBr
The lithium bromide forms a complex with the methyllithium(917-54-4). Most commercially available methyllithium(917-54-4) consists of this complex. "Halide-free" methyllithium(917-54-4) is prepared from methyl chloride. Lithium chloride precipitates from the diethyl ether since it does not form a strong complex with methyllithium(917-54-4). The filtrate consists of fairly pure methyllithium(917-54-4).

METHYLLITHIUM Safety Profile

Ignites spontaneously in air. See also LITHIUM COMPOUNDS.

METHYLLITHIUM Specification

Bonding
These clusters are considered "electron-deficient," that is, they do not follow the octet rule because the molecules lack sufficient electrons to form four 2-centered, 2-electron bonds around each carbon atom, in contrast to most organic compounds. The hexamer is a 30 electron compound (30 valence electrons.) If one allocates 18 electrons for the strong C-H bonds, 12 electrons remain for Li-C and Li-Li bonding. There are six electrons for six metal-metal bonds and one electron per methyl-η3 lithium interaction.

The strength of the C-Li bond has been estimated at around 57 kcal/mol from IR spectroscopic measurements.

Product Name

METHYLLITHIUM

Synthetic route

METHYLLITHIUM Chemical Properties

METHYLLITHIUM Production

METHYLLITHIUM Safety Profile

METHYLLITHIUM Specification

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