7412-67-1

Basic information

• Product Name: NEOPENTYLLITHIUM
• Synonyms: NEOPENTYLLITHIUM;1-Lithio-2,2-dimethylpropane;2,2-Dimethylpropyllithium;Neopentyllithium solution
• CAS NO: 7412-67-1
• Molecular Formula: C₅H₁₁Li
• Molecular Weight: 78.08
• Mol File: 7412-67-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 130 °C (sublm)(Press: 0.00001 Torr)
• Flash Point: -30 °C
• Appearance: /
• CAS DataBase Reference: NEOPENTYLLITHIUM(CAS DataBase Reference)
• NIST Chemistry Reference: NEOPENTYLLITHIUM(7412-67-1)
• EPA Substance Registry System: NEOPENTYLLITHIUM(7412-67-1)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14/15-17-34-48/20-50/53-63-65-67
• Safety Statements: 26-36/37/39-43-45
• Hazardous Substances Data: 7412-67-1(Hazardous Substances Data)

Usage

General Description

NEOPENTYLLITHIUM is a highly reactive chemical compound that is used as a strong base and nucleophile in organic synthesis. It is composed of lithium and a neopentyl group, and is known for its ability to selectively deprotonate substrates in reactions with a high degree of regioselectivity. NEOPENTYLLITHIUM is often used in the preparation of complex organic molecules, as well as in the production of certain pharmaceuticals and agrochemicals. It is also utilized in the manufacturing of polymers and as a reagent for the modification of organic molecules. However, due to its highly reactive nature and potential for violent reactions with water and air, NEOPENTYLLITHIUM should be handled and stored with extreme caution.

InChI:InChI=1/C5H11.Li/c1-5(2,3)4;/h1H2,2-4H3;/rC5H11Li/c1-5(2,3)4-6/h4H2,1-3H3

Upstream product

• 753-89-9 neopentyl chloride 
• 15501-33-4 neopentyl iodide 

Downstream Products

• 53317-07-0 (1s,5s)-9-neopentyl-9-bora-bicyclo[3.3.1]nonane 
• 32579-71-8 2,2,4,4-tetramethyl-3-neopentylpentan-3-ol 
• 20818-94-4 dineopentyl-tert-butylcarbinol 
• 20818-95-5 trineopentylcarbinol 
• 63383-01-7 9-neopentylantracene 
• 868-91-7 2,2,5,5-tetramethylhexan-3-one 
• 20818-91-1 3-tert-butyl-2,2,5,5-tetramethyl-3-(4-nitro-benzoyloxy)-hexane 
• 22822-86-2 2-tert.-Butyl-1-neopentyl-vinyl-p-nitrobenzoat 
• 20818-93-3 4-(2,2-dimethyl-propyl)-2,2,6,6-tetramethyl-4-(4-nitro-benzoyloxy)-heptane 
• 7489-70-5 dimethyl(neopentyl)silane 
• 89372-93-0 1,2-Dichloro-1,2-bis-(2,2-dimethyl-propyl)-1,2-dimethyl-disilane 
• 1071-81-4 2,2,5,5-tetramethylhexane 
• 110139-85-0 Chloro-(2,2-dimethyl-propyl)-phenyl-silane 
• 55204-72-3 Neopentyl(trimethyl)stannane 

Relevant articles and documents

Carbanions 27. Rearrangements of (9-alkyl-9-fluorenyl)-methyllithium (or cesium) and 2,2-diphenyl-3,3-dimethyl-butyllithium

A study has been made upon the products from warming various (9-alkyl-9-fluorenyl)methyllithium (or cesium) compounds in THF to near 0°C followed by carbonation. When the 9-alkyl group is ethyl, the result is chiefly the protonated product (9-alkyl-9- fluorenyl)methane; a similar product evidently is formed when the 9-alkyl group is 1-norbornyl. When the 9-alkyl group is tert-butyl, the minor product is 9-neopentylfluorene-9-carboxylic acid from a [1,2]-migration of the tert-butyl group while the major product is 9-methylfluorene-9-carboxylic acid from an intramolecular elimination as shown by deuterium labeling. When the 9-alkyl is neopentyl, the major product is 9-neopentyl-9,10-dihydro-phenanthrene-9-carboxylic acid along with some 9-neopentylphenanthrene which becomes the major product in diethyl ether solution at 35°C. 2,2-Diphenyl-3,3-dimethylbutyllithium undergoes predominantly [1,2]-phenyl migration in THF at 0°C. From an x-ray crystal study upon 9-tert-butyl-9-(chloromethyl)fluorene and 9-neopentyl-9-(chloromethyl) fluorene, it is concluded that steric acceleration is responsible for the unusual reactions of (9-alkyl-9-fluorenyl)methyllithiums when the 9-alkyl groups are tert-butyl and neopentyl.