13397-96-1

Basic information

• Product Name: Benzene, 1-bromo-2-pentyl-
• CAS NO: 13397-96-1
• Molecular Formula: C11H15Br
• Molecular Weight: 227.144
• Mol File: 13397-96-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-bromo-2-pentyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-2-pentyl-(13397-96-1)
• EPA Substance Registry System: Benzene, 1-bromo-2-pentyl-(13397-96-1)

Safety Data

• Hazardous Substances Data: 13397-96-1(Hazardous Substances Data)

Upstream product

• 109-72-8 n-butyllithium 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 16692-57-2 1-bromo-2-(pent-1-en-1-yl)benzene 
• 54031-00-4 1-bromo-2-((trimethylstannyl)methyl)benzene 
• 1529-47-1 chlorotrimethylgermane 
• 6630-33-7 ortho-bromobenzaldehyde 
• 122-56-5 tributyl borane 
• 158918-49-1 N’-(2-bromobenzylidene)-4-methylbenzenesulfonohydrazide 
• 778-28-9 butyl para-toluenesulfonate 

Downstream Products

• 1438826-28-8 C₂₂H₃₉BO₃Si 
• 1438824-72-6 2-pentylphenyl dimethylsilane 
• 119150-38-8 <2-n-Amyl-benzhydryl>-<2-dimethylamino-aethyl>-aether 
• 101787-36-4 2-n-Amyl-benzhydrol 

Relevant articles and documents

Multiple organolithium generation in the continuous flow synthesis of amitriptyline

A continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol. Copyright

Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane

Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

Selective lithiation of 1-bromo-2-((trimethylstannyl)methyl)benzene: Synthesis of 1-bromo-2-(lithiomethyl)benzene, 1-lithio-2-((trimethylstannyl)methyl)benzene, and α,2-dilithiotoluene

Reactions of 1-bromo-2-((trimethylstannyl)methyl)benzene (1) with n-butyllithium and tert-butyllithium have been investigated. With n-butyllithium in tetrahydrofuran (THF) at -70°C, the only observed process was lithium-tin exchange, yielding 1-bromo-2-(lithiomethyl)benzene (2). In contrast, lithium-halogen exchange occurred when 1 was treated with tert-butyllithium in diethyl ether at -80°C to give 1-lithio-2-((trimethylstannyl)methyl)benzene (3). α,2-Dilithiotoluene could be prepared in high yield from 3 and tert-butyllithium in either diethyl ether (room temperature) or THF (-80°C).