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Methyllithium

Product Name
Methyllithium
CAS No.
917-54-4
Chemical Name
Methyllithium
Synonyms
MELI;LITHIUM METHANIDE;Methyllithium solution;Methyllithium lithium bromide complex solution;Lowhalide;1-2MinEther;methyl-lithiu;METHYLLITHIUM;Methy-Lithium;LITHIUM METHYL
CBNumber
CB7234211
Molecular Formula
CH3Li
Formula Weight
21.98
MOL File
917-54-4.mol
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Methyllithium Property

Melting point:
70-71℃
Boiling point:
88℃
Density 
0.85 g/mL at 20 °C
vapor density 
3 (vs air)
Flash point:
5 °F
storage temp. 
2-8°C
form 
Solution
Specific Gravity
0.83
color 
Colorless to yellow
Water Solubility 
Reacts with water.
Sensitive 
Air & Moisture Sensitive
Hydrolytic Sensitivity
9: reacts extremely rapidly with atmospheric moisture - may be pyrophoric - glove box or sealed system required
BRN 
3587162
Exposure limits
ACGIH: TWA 400 ppm; STEL 500 ppm
OSHA: TWA 400 ppm(1200 mg/m3)
NIOSH: IDLH 1900 ppm
CAS DataBase Reference
917-54-4(CAS DataBase Reference)
EPA Substance Registry System
Lithium, methyl- (917-54-4)
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Safety

Hazard Codes 
F+,C,N,F,Xn,Xi
Risk Statements 
12-15-17-22-34-66-67-65-51/53-11-36/37/38-36/38-19-40-36/37-37-14/15
Safety Statements 
16-26-36/37/39-45-43-30-60-62-61-36/37
RIDADR 
UN 3399 4.3/PG 1
WGK Germany 
2
10
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
I
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H250Catches fire spontaneously if exposed to air

H252Self-heating in large quantities; may catch fire

H260In contact with water releases flammable gases which may ignite spontaneously

H302Harmful if swallowed

H303May be harmfulif swallowed

H304May be fatal if swallowed and enters airways

H311Toxic in contact with skin

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

H336May cause drowsiness or dizziness

H401Toxic to aquatic life

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P222Do not allow contact with air.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

P370+P378In case of fire: Use … for extinction.

P402+P404Store in a dry place. Store in a closed container.

P405Store locked up.

P422Store contents under …

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
197343
Product name
Methyllithium solution
Purity
1.6M in diethyl ether
Packaging
1l
Price
$309
Updated
2024/03/01
Sigma-Aldrich
Product number
186201
Product name
Methyllithium lithium bromide complex solution
Purity
1.5?M in diethyl ether
Packaging
100mL
Price
$97.3
Updated
2024/03/01
Sigma-Aldrich
Product number
186201
Product name
Methyllithium lithium bromide complex solution
Purity
1.5?M in diethyl ether
Packaging
4x25ml
Price
$125
Updated
2024/03/01
Sigma-Aldrich
Product number
186201
Product name
Methyllithium lithium bromide complex solution
Purity
1.5?M in diethyl ether
Packaging
800mL
Price
$576
Updated
2024/03/01
Sigma-Aldrich
Product number
186201
Product name
Methyllithium lithium bromide complex solution
Purity
1.5?M in diethyl ether
Packaging
1L
Price
$620
Updated
2024/03/01
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Methyllithium Chemical Properties,Usage,Production

Chemical Properties

Methyllithium is a colorless to yellowish solution, It is insoluble in hydrocarbon solvents although propyllithium and the higher homologues are miscible in hydrocarbons. Methyllithium is soluble in diethyl ether to about 6% by weight at room temperature (with or without lithium bromide) and is a little less soluble in tetrahydrofuran. Cooling of these solutions produces clear, colorless crystals of methyllithium etherate. Methyllithium is stable to about 200°C, at which temperature it disproportionates to dilithiomethane and methane.

Uses

There are no significant industrial uses of methyllithium, but it is widely used in the laboratory in Grignard type reactions.
Methyllithium is an organolithium reagent mainly used for deprotonation and as a source of methyl anion. It is a strong base and a strong nucleophile.

Uses

Methyllithium lithium bromide complex solution (MeLi.LiBr) can be used as a methylating agent for the α-methylation of alkoxyaryl ketones.

Definition

ChEBI: Methyllithium is an alkyllithium compound and a one-carbon compound.

Preparation

Methyllithium is produced industrially by the reaction of methyl chloride or methyl bromide with lithium metal dispersion in diethyl ether. The reaction with methyl chloride yields a solution of methyllithium and a precipitate of lithium chloride which may be readily separated. When methyl bromide is used, the lithium bromide byproduct remains in solution and complexes with the methyllithium. This reduces the reactivity of the methyllithium and, in certain cases, affects its usefulness. On the other hand, the less reactive complex is more stable in diethyl ether. Methyllithium produced from methyl chloride contains only about 0.3 % lithium chloride in a 5 % solution in diethyl ether. It is more reactive than the lithium bromide complex, but decomposes at the rate of 1 % of the contained methyllithium per year (that is 5.00 % solution goes to 4.95 %) at room temperature. The decomposition by ether cleavage results in methane and ethylene formation which increases the pressure in the container on long storage. Methyllithium can be prepared easily in tetrahydrofuran but it has a half-life of only about 2 days at room temperature due to solvent cleavage.

Application

Methyllithium solution (1.6M in diethyl ether) has been used for the asymmetric allylic alkylation (AAA) of allylic electrophiles in the presence of a chiral copper catalyst. This protocol leads to the C-C bond formation of tertiary and quaternary stereogenic centers with high enantioselectivity. It can also be used for the synthesis of (?)-salsolidine by reacting with 6,7-dimethoxy-3,4-dihydroisoquinoline in the presence of (?)-sparteine as a chiral ligand.

Hazard

Flammable, dangerous fire and explosionrisk, self-ignites in air.

Methyllithium Preparation Products And Raw materials

Raw materials

Preparation Products

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Methyllithium Suppliers

Huangshi Bo’Er Chemical Co., Ltd.
Tel
0714-6401888 18671400300
Fax
0714-6401888
Email
273568016@qq.com
Country
China
ProdList
537
Advantage
58
Shaoxing youli biology science and technology co., ltd
Tel
0575-82148339 15967563458
Email
704090688@qq.com
Country
China
ProdList
28
Advantage
58
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing dtftchem Technology Co., Ltd.
Tel
010-60275820 13031183356
Fax
010-60270825
Email
elainezt@sina.com
Country
China
ProdList
1390
Advantage
62
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
Advantage
60
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
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View Lastest Price from Methyllithium manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Methyllithium 917-54-4
Price
US $9.90/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2021-11-08
Hebei Mojin Biotechnology Co., Ltd
Product
Methyllithium 917-54-4
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-17
Career Henan Chemical Co
Product
METHYLLITHIUM 917-54-4
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1
Release date
2018-08-06

917-54-4, MethyllithiumRelated Search:


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