109962-22-3

Usage

Chemical structure

1-Chloro-6-methylnaphthalene consists of a naphthalene ring with a methyl group and a chlorine atom attached at specific positions.

Physical state

It is a clear, colorless to light yellow liquid.

Odor

It has a strong, sweet odor.

Applications

a. Intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes.
b. Used in the production of corrosion inhibitors, lubricants, and surfactants.
c. Employed as a reagent in various organic reactions, including Suzuki-Miyaura coupling and Friedel-Crafts acylation.

Safety precautions

It should be handled with caution as it may be harmful if swallowed, inhaled, or comes into contact with the skin or eyes.

Upstream product

• 103861-98-9 1-methyl-3-(2,4,4,4-tetrachloro-butyl)-benzene 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 55614-74-9 3-chlorobenzyl magnesium bromide 
• 412041-50-0 1,2-diethynyl-4-methylbenzene 
• 3333-20-8 1-allyl-3-methylbenzene 

Relevant academic research and scientific papers

A remarkably simple and efficient benzannulation reaction

(Chemical Equation Presented) On a short fuse: Although fused aromatic rings are common structural motifs in natural products, there are relatively few direct methods for the preparation of such systems from acyclic precursors. An atom-transfer radical cyclization carried out under microwave (MW) irradiation has now been developed which gives rapid access to functionalized aromatic compounds from readily available starting materials (see scheme).

A Visible Light and Iron-mediated Carbocationic Route to Polysubstituted 1-Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes

A wide array of polysubstituted 1-bromo and chloronaphthalenes are obtained from coupling of allylbenzenes and polyhalomethanes. The reaction is mediated by iron metal under visible light irradiation and proceeds via a Kharasch addition intermediate followed by intramolecular FeIII mediated Friedel-Crafts alkylation, with the formation of two Csp2?Csp2 bonds in the process. This method gives easy access to 1-halonaphthalenes with substituent(s) at C-5 to C-8 that are otherwise hard to synthesize. (Figure presented.).

New reactivity patterns of copper(I) and other transition metal NHC complexes: application to ATRC and related reactions

Pre-formed transition metal-NHC complex is shown to be an effective catalyst for Atom Transfer Radical Cyclisation (ATRC) reactions.

PROCESS FOR SYNTHESIS OF AROMATIC COMPOUNDS

The present invention refers to a process for preparing a compound of the formula (I) wherein R denotes an organic radical which, together with the two carbon atoms to which it is bonded, forms a carbocyclic or heterocyclic ring; R1, R2, R3 and X, independently, denote hydrogen, halogen, nitro, cyano or an organic radical; or R1 and R2 or R2 and R3, together with the carbon atoms to which they are bonded, form a ring; which comprises exposing a compound of the formula (II) wherein R1, R2, R3 and X are defined as given above and Y and Z, independently, have one of the meanings of X; to an energy source in the presence of a catalyst system.

Regioselective haloaromatization of 1,2-bis(ethynyl)benzene via halogen acids and PtCl2. Platinum-catalyzed 6-π electrocyclization of 1,2-bis(1′-haloethenyl)benzene intermediates

Treatment of 1,2-bis(ethynyl)benzene (1) with aqueous HX (X = Br, I) in hot 3-pentanone (100-105 °C, 2 h) afforded 1,2-bis(1′-haloethenyl)benzene species 2-Br and 2-I in 98% and 95% yields, respectively. The hydrochlorination of endiyne 1 failed to proceed at elevated temperature but was implemented efficiently by PtCl2 (5 mol %) in hot 3-pentanone (100 °C, 2 h) to give 1,2-bis(1′-chloroetheny)benzene 2-Cl in 80% yield. In the presence of PtCl2 (5 mol %), these halides 2-Cl, 2-Br, and 2-I were subsequently converted to 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in the mother solution via sequential 6-π electrocyclization and dehalogenation reactions. PtCl2 (5 mol %) also effected direct haloaromatization of endiyne 1 with HX (X = Cl, Br, I) and gave 1-halonaphthalenes 3-Cl, 3-Br, and 3-I in 64-71% yields. This investigation reports the scope and the regioselectivity of haloaromatization of various enediynes catalyzed by PtCl2.

The first helical-chiral phosphane ligands: rac-[5]- and rac-[6]-heliphos

The syntheses of two helical, chiral phosphanes in their racemic forms are described. Their helicene backbone was built up using an improved photocyclization approach. The phosphorus functionalities were introduced in the last step. Up to now, separation of the enantiomers of the helicene phosphanes could be achieved analytically but not on a preparative scale.