3314-49-6

Basic information

• Product Name: N-OCTYLLITHIUM
• Synonyms: N-OCTYLLITHIUM
• CAS NO: 3314-49-6
• Molecular Formula: C₈H₁₇Li
• Molecular Weight: 120.16
• Mol File: 3314-49-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-OCTYLLITHIUM(CAS DataBase Reference)
• NIST Chemistry Reference: N-OCTYLLITHIUM(3314-49-6)
• EPA Substance Registry System: N-OCTYLLITHIUM(3314-49-6)

Safety Data

• Hazardous Substances Data: 3314-49-6(Hazardous Substances Data)

Usage

General Description

N-octyllithiums is an organometallic compound that consists of a lithium atom bonded to an octyl group. It is a strong base and a powerful nucleophile, commonly used in organic synthesis as a reagent for the formation of carbon-carbon bonds. N-octyllithium is highly reactive and must be handled with extreme caution, as it is pyrophoric and reacts violently with water, air, or any protic solvent, releasing flammable and toxic gases. It is typically stored and handled under inert atmosphere conditions, and its use requires rigorous safety measures to prevent accidents. Nonetheless, N-octyllithium is an important tool in chemical research and industrial processes for the synthesis of complex organic compounds.

Upstream product

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Relevant articles and documents

Alkyllithium Reagents from Alkyl Halides and Lithium Radical Anions

The reaction of alkyl halides with three different lithium radical anions, lithium naphthalene (LiN), lithium di-tert-butylnaphthalene (LiDBN), and lithium di-tert-butylbiphenyl (LiDBB), was studied.The reaction of alkyl halides with an excess of LiN, LiDBN, or LiDBB in THF at -78 deg C leads to a consistently high yield (96-100percent) of reduction products (RH, RLi) with a high degree of formation of RLi (anion trapping 93-95percent) in the case of LiDBB.LiDBN consistently produces high yields of reduction products (89-99percent) with widely variable amounts of anion trapping (21-88percent), while LiN provides variable yields of reduction (39-99percent) and anion trapping (24-65percent).Variation of the concentration of lithium bromide and naphthalene and the ratio of alkyl halide to naphthalene in conjunction with the use of deuterium tracer experiments provided evidence consistent with a competition between metalation of the lithium dihydronaphthalenedicarboxylate by alkyllithium and carbonation of alkyllithium in the carbonation step of the analysis.