84189-17-3

Basic information

• Product Name: 2,3-DIBROMOMETHYLPENTANE
• Synonyms: 2,3-DIBROMOMETHYLPENTANE
• CAS NO: 84189-17-3
• Molecular Formula: C₆H₁₂Br₂
• Molecular Weight: 243.96748
• Mol File: 84189-17-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-DIBROMOMETHYLPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIBROMOMETHYLPENTANE(84189-17-3)
• EPA Substance Registry System: 2,3-DIBROMOMETHYLPENTANE(84189-17-3)

Safety Data

• Hazardous Substances Data: 84189-17-3(Hazardous Substances Data)

Usage

General Description

2,3-Dibromomethylpentane is a chemical compound with the molecular formula C6H12Br2. It is a fluorinated compound that consists of a pentane backbone with two bromine atoms and a methyl group attached to the third carbon. 2,3-DIBROMOMETHYLPENTANE is often used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It is known for its potential as a reagent in various chemical reactions, and its structure makes it a valuable intermediate in the synthesis of more complex molecules. 2,3-Dibromomethylpentane is also known for its high reactivity, as the bromine atoms can easily participate in substitution reactions, making it a versatile compound for use in chemical transformations.

Upstream product

• 187737-37-7 propene 
• 74-99-7 prop-1-yne 
• 674-76-0 (E)-4-methylpent-2-ene 
• 691-38-3 (Z)-4-methyl-2-pentene 

Downstream Products

• 691-38-3 (Z)-4-methyl-2-pentene 
• 200395-89-7 dibromo di-n-hexyl tellurium(IV) 
• 4461-48-7 4-methyl-2-pentene 

Relevant articles and documents

Debrominations of vic-Dibromides with Diorganotellurides. 1. Stereoselectivity, Relative Rates, and Mechanistic Implications

Debrominations of vic-dibromides with diaryl tellurides 1-4 and di-n-hexyl telluride (9) are described. A mechanistic explanation of the debromination is offered which accounts for several key experimental observations: (1) the reaction is highly stereoselective with erythro-dibromides giving trans-olefins and threo-dibromides giving cis-olefins, (2) the reaction is accelerated by more electron-rich diorganotellurides, (3) the reaction is accelerated in a more polar solvent, (4) the reaction is accelerated by the addition of carbocation-stabilizing substituents to the carbons bearing the bromo substituents, and (5) erythro-dibromides are much more reactive than threo-dibromides. It is proposed that bromonium ion formation from the vic-dibromide is slow and rate-determining. Bromonium ion formation is followed by rapid scavenging of "Br-" by the diorganotelluride. The bromonium ion formation provides stereoselectivity and eclipsing interactions lower the reactivity of threo-dibromides. No intermediate species were observed by 1H NMR.