197343
Methyllithium solution
1.6 M in diethyl ether
Synonym(s):
Lithium methanide, MeLi
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About This Item
Empirical Formula (Hill Notation):
CH3Li
CAS Number:
Molecular Weight:
21.98
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3587162
Concentration:
1.6 M in diethyl ether
Form:
liquid
vapor density
3 (vs air)
Quality Segment
form
liquid
composition
halide, ~0.05 M
concentration
1.6 M in diethyl ether
density
0.732 g/mL at 25 °C
storage temp.
2-8°C
SMILES string
[Li]C
InChI
1S/CH3.Li/h1H3;
InChI key
DVSDBMFJEQPWNO-UHFFFAOYSA-N
General description
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.
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.
Packaging
The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 1
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
Hazard Classifications
Acute Tox. 4 Oral - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react. 1
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