50585-29-0

Usage

Uses

Used in Chemical Synthesis Industry:
1,8-Bis(chloromethyl)naphthalene is used as a precursor in the synthesis of various organic compounds for different purposes. Its chloromethyl groups can be easily replaced or modified, making it a versatile building block in organic chemistry.
Specifically, 1,8-Bis(chloromethyl)naphthalene is used as a starting material for the production of acenapthene through a process called laser flash photolysis. This technique involves the use of a laser to rapidly break chemical bonds, allowing for the formation of new compounds, such as acenapthene, which has its own set of applications and properties.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 653, 1956 DOI: 10.1021/ja01584a036

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 2026-08-6 naphthalene-1,8-diyldimethanol 

Downstream Products

• 97840-91-0 1,8-bis(phenylthiomethyl)-naphthalene 
• 2131-41-1 1,4,5-trimethylnaphthalene 
• 73892-41-8 1,8-bis[(diphenylphosphino)methyl]naphthalene 
• 83-32-9 acenaphthene 
• 208-96-8 acenaphthylene 
• 569-41-5 1,8-dimethylnaphthalene 

Relevant academic research and scientific papers

Stereospecific Synthesis of 2,3-Dihydro-2-metallaphenalenes, meso- , via an Unstable Dilithium Reagent, 2> (tmeda = tetramethylethylenediamine), which is converted into the Complex containing a Silicon Heterocycl...

In situ Grignard reactions of 1,8-(ClCH2)2C10H6 have yielded 2,3-dihydro-2,2-dimethyl-2-silaphenalene, which can be selectively monolithiated at the 1-position, and 1,8-(Me3SiCH2)2C10H6, a compound readily dilithiated and subsequently converted into the zirconium and hafnium metallacycles, meso-; the dilithium complex is converted into the complex containing a silicon heterocycle dicarbanion and characterized as the substituted silaphenalene, the same product as the ClSiMe3 adduct of mono-lithiated silaphenalene.

Chemistry of 2,3-Dihydro-2-metallaphenalenes. Part 1. Synthesis of (R=R'=H; R=R'=SiMe3; and R,R'=H,SiMe3) and Formation of the Compound via Decomposition of 2>; Crystal Structures of two Polymorphs of the Silicon Heterocycle Dilithium ...

The complexes 2> (9) (tmen=NNN'N'-tetramethylethylenediamine) and (13) have been prepared via metallation of species formed by in situ Grignard trapping reactions of 1,8-(ClCH2)2C10H6 with SiMe3Cl and SiMe2Cl2 respectively; synthesis of the siline, meso- from (9) is also described.In hexane, (9) decomposes to (10) to yield the compound on the addition of aqueous HCl, the same product as that obtained from a reaction of (13) with SiMe3Cl.The nature of (10) has been established by X-ray structure determination of two polymorphs, α and β, which differ both in the mode of interaction of the Li(tmen)(+) moieties with the carbanion 6:η3 (α), cf. η4:η3 (β)> and the conformation of the heterocyclic ring.

Mild and efficient synthesis of 1,8-naphthalide and 1,8- naphthalenedimethanol

Mild and efficient procedures have been developed for synthesis of 1,8-naphthalide and 1,8-naphthalenedimethanol. In an ice-water bath, 1,8-naphthalide was prepared from 1,8-naphthlic anhydride using LiAlH 4 as reducing agent. 1,8-Naphthalenedi