3525-31-3

Basic information

• Product Name: Pentyllithium solution
• Synonyms: Pentyllithium solution;Amyllithium;Pentyllithium （1.3M in heptane）
• CAS NO: 3525-31-3
• Molecular Formula: C₅H₁₁Li
• Molecular Weight: 78.08184
• Mol File: 3525-31-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 0.708 g/mL at 25 °C
• CAS DataBase Reference: Pentyllithium solution(CAS DataBase Reference)
• NIST Chemistry Reference: Pentyllithium solution(3525-31-3)
• EPA Substance Registry System: Pentyllithium solution(3525-31-3)

Safety Data

• Hazard Codes: F,T
• Statements: 45-46-11-14-17-35-65
• Safety Statements: 53-16-26-36/37/39-45-62
• Hazardous Substances Data: 3525-31-3(Hazardous Substances Data)

Usage

General Description

Pentyllithium solution is a chemical compound that consists of a lithium atom bonded to a pentyl group. It is commonly used as a strong base and nucleophile in organic chemistry reactions. Pentyllithium solution is highly reactive and must be handled with extreme caution due to its pyrophoric nature, meaning it can spontaneously ignite in air. It is typically used in the synthesis of organic compounds, such as pharmaceuticals, and in the modification of polymers and plastics. The compound is also known for its ability to form strong carbon-carbon bonds in the presence of various electrophiles, making it a valuable tool in organic synthesis. Due to its reactivity, pentyllithium solution is typically stored and handled in a dry, inert atmosphere to prevent any unintended reactions.

Upstream product

• 543-59-9 1-Chloropentane 
• 110-53-2 1-Bromopentane 
• 628-17-1 amyl iodide 

Downstream Products

• 124-18-5 decane 
• 583-48-2 3,4-dimethylhexane 
• 2216-33-3 3-methyl-octane 
• 110-43-0 n-pentyl methyl ketone 
• 18742-63-7 pentyl-triphenyl-silane 
• 6485-78-5 tri(n-pentyl)silane 
• 66-25-1 hexanal 
• 7003-82-9 (4-toy-α-OH)2Si(Oet)2 
• 69393-85-7 1-Hept-1-ynyloxy-4-methyl-benzene 
• 92210-69-0 3-pentyl-1-<(trimethylsilyl)oxy>cyclohexene 
• 98409-21-3 2-hydroxy-3-octanone 
• 84435-13-2 (+)-(2S)-2-hydroxyoctan-3-one 
• 131216-45-0 (E)-1-phenyl-3-nonene 
• 127411-91-0 Trimethyl-{1-[3-phenyl-prop-(Z)-ylidene]-hexyl}-silane 

Relevant articles and documents

Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform

Classical synthetic approaches to highly unsaturated polyene/yne natural products rely on iterative cross-coupling of linear fragments. Herein, we present an expeditious and unified approach to the unsaturated backbone of polyacetylenes via domino cuprate addition/4π-electrocyclic ring opening of a stereodefined cyclobutene intermediate. This sets the stage for a detailed biological assessment of the role of Virol A and Cicutoxin as inhibitors of GABA induced chloride currents, providing further insight into the interaction of these highly potent toxins towards the GABAA receptor, including the structure-activity relationship of the derivatives.

Facial selectivity in the addition of lithium dimethylcuprate to 6-substituted tricyclo[5.2.1.02,6]deca-4,8-dienones. Synthesis of β-substituted cyclopentenones using flash vacuum thermolysis

The stereoselectivity of the nucleophilic addition of lithium dimethylcuprate and lithium di-n-pentylcuprate to 6-substituted tricyclo[5.2.1.02,6]deca-4,8-dienones was investigated. It was shown that substituents at the 6-position can either exert a steric effect or an electronic effect. Steric approach control predominantly giving the endo product was observed for 6-alkyl substituents. Stereoelectronic control could be adequately rationalised using the Cieplak model. Flash vacuum thermolysis was used to prepare a series of β-substituted cyclopentenoids. The sequence leading to cyclopentenoids has an attractive scope.

Stereoselective Synthesis of 2Z,4E-Dienals by Addition of Organometallic Reagents to Pyrylium Perchlorate

A facile and stereoselective approach to 2Z,4E-dienals and derived products is presented.The method involves addition of an organometallic reagent to a pyrylium salt, followed by electrocyclic ring-opening of the intermediate 2H-pyran, to give the desired Z,E-dienal, usually with greater than 95percent stereochemical purity.These dienals may be trapped in situ with a second organometallic reagent, or oxidised or redused, without loss of stereochemical integrity.The synthesis of (1,3Z,5E)-undeca-1,3,5-triene, a component of the essential oils of the brown Hawaiian seaweeds Dictyopteris plagiogramma and D. australis, is reported to illustrate the simplicity of the procedure.