19190-48-8

Usage

Type of compound

Organohalogen compound

Derivative of

Naphthalene (a polycyclic aromatic hydrocarbon)

Structural features

a. Bromine atom at the 1-position
b. Chlorine atom at the 8-position
c. Methyl group attached to the chlorine atom

Common uses

Intermediate in the synthesis of other organic chemicals, manufacturing of pharmaceuticals, agrochemicals, and other fine chemicals

Reactivity

Versatile building block in organic synthesis

Safety classification

Hazardous substance

Handling precautions

Follow proper safety protocols and handle with care

Upstream product

• 14938-58-0 1-bromo-8-hydroxymethylnaphthalene 
• 1729-99-3 8-bromonaphthalene-1-carboxylic acid 

Downstream Products

• 638166-53-7 1-CH₂PHPh(BH₃)-naphthalene 
• 1072102-48-7 ((8-bromonaphthalen-1-yl)methyl)(phenyl)phosphine-borane 
• 1072102-64-7 Cy-AcePhos 

Relevant academic research and scientific papers

Platinum-catalyzed enantioselective tandem alkylation/arylation of primary phosphines. Asymmetric synthesis of p-stereogenic 1-phosphaacenaphthenes

(Chemical Equation Presented) Enantioselective tandem alkylation/arylation of primary phosphines with 1-bromo-8-chloromethylnaphthalene catalyzed by Pt(DuPhos) complexes gave P-stereogenic 1-phosphaacenaphthenes (AcePhos) in up to 74% ee. Diastereoselective formation of four P-C bonds in one pot with bis(primary) phosphines gave C2-symmetric diphosphines, including the ophenylene derivative DuAcePhos, for which the rac isomer was formed with high enantioselectivity. These reactions, which appear to proceed via an unusual metal-mediated nucleophilic aromatic substitution pathway, yield a new class of heterocycles with potential applications in asymmetric catalysis.