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197343

Sigma-Aldrich

Methyllithium solution

1.6 M in diethyl ether

Synonyme(s) :

Lithium methanide, MeLi

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About This Item

Formule empirique (notation de Hill):
CH3Li
Numéro CAS:
917-54-4
Poids moléculaire :
21.98
Beilstein:
3587162
Numéro MDL:
MFCD00008253
Code UNSPSC :
12352103
ID de substance PubChem :
24851824
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Densité de vapeur

3 (vs air)

Niveau de qualité

100

Forme

liquid

Composition

halide, ~0.05 M

Concentration

1.6 M in diethyl ether

Densité

0.732 g/mL at 25 °C

Température de stockage

2-8°C

Chaîne SMILES 

[Li]C

InChI

1S/CH3.Li/h1H3;

Clé InChI

DVSDBMFJEQPWNO-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.[1]

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.[2] 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.[3]

Conditionnement

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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Informations légales

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Pictogrammes

FlameCorrosionExclamation mark
GHS02,GHS05,GHS07

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Oral - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Risques supp

EUH019,EUH066

Code de la classe de stockage

4.2 - Pyrophoric and self-heating hazardous materials

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

1.4 °F - closed cup

Point d'éclair (°C)

-17 °C - closed cup

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Certificats d'analyse (COA)

Lot/Batch Number
SHBS3927
SHBR0418
STBL2809
STBL2402
STBK7721

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

A Simplified Approach with 3D Visuals
Vasishta Bhatt
Essentials of Coordination Chemistry: A Simplified Approach with 3D Visuals, 183-183 (2015)
Enantioselective addition of organolithium reagents to 3, 4-dihydroisoquinoline in the presence of (?)-sparteine as an external ligand. Application for the synthesis of isoquinoline alkaloids.
Chrzanowska M
Tetrahedron Asymmetry, 12(10), 1435-1440 (2001)
Kiran Kumar Solingapuram Sai et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 129, 57-61 (2017-08-15)
We automated radiochemical synthesis of 1-[
Mingyang Zhang et al.
Macromolecular rapid communications, 41(18), e2000323-e2000323 (2020-08-11)
Carbon monoxide (CO) has emerged as a potential therapeutic agent for the treatment of many diseases. However, the therapeutic outcome is highly dependent on the dosages and administration sites. Hence, there is mounting interest in the development of CO-releasing materials
Cu-catalyzed enantioselective allylic alkylation with organolithium reagents.
Hornillos V, et al.
Nature Protocols, 12(3), 493-493 (2017)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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