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468568

Sigma-Aldrich

Hexyllithium solution

2.3 M in hexane

Synonym(s):

1-Hexyllithium, n-Hexyllithium, Hexane - lithium complex

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About This Item

Linear Formula:
CH3(CH2)5Li
CAS Number:
21369-64-2
Molecular Weight:
92.11
Beilstein:
3600261
MDL number:
MFCD00191446
UNSPSC Code:
12352103
PubChem Substance ID:
24870524
NACRES:
NA.22

Quality Level

200

concentration

2.3 M in hexane

bp

69 °C

density

0.708 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li]CCCCCC

InChI

1S/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3;

InChI key

RMKNFFPDYCVCDI-UHFFFAOYSA-N

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General description

Hexyllithium solution is an organolithium compound used in organic synthesis as a strong base, alkylating agent, and lithiation reagent.

Application

Hexyllithium solution can be used as an alkylating agent in the:
  • Ni-catalyzed cross-coupling with aryl halides.
  • Cu-catalyzed enantioselective allylic alkylation.
It can also be used as a lithiation agent for the lithiation of azetidines.

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

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1A - STOT RE 2 Inhalation - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Nervous system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

15.8 °F - closed cup

Flash Point(C)

-9 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jacqueline E Cloud et al.
Angewandte Chemie (International ed. in English), 53(52), 14527-14532 (2014-11-05)
The synthesis of colloidal nanocrystals (NCs) of lithiated group 14 elements (Z=Si, Ge, and Sn) is reported, which are Li4.4 Si, Li3.75 Si, Li4.4 Ge, and Li4.4 Sn. Lix Z compounds are highly reactive and cannot be synthesized by existing methods.

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