71778-30-8

Basic information

• Product Name: 1-Chloro-7-methylnaphthalene
• Synonyms: 1-Chloro-7-methylnaphthalene;NAPHTHALENE, 1-CHLORO-7-METHYL-
• CAS NO: 71778-30-8
• Molecular Formula: C₁₁H₉Cl
• Molecular Weight: 176.64216
• Mol File: 71778-30-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Chloro-7-methylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-7-methylnaphthalene(71778-30-8)
• EPA Substance Registry System: 1-Chloro-7-methylnaphthalene(71778-30-8)

Safety Data

• Hazardous Substances Data: 71778-30-8(Hazardous Substances Data)

Usage

Type of Compound

Chlorinated derivative of 7-methylnaphthalene

Aromatic Hydrocarbon

Widely used in various applications

Primary Use

Intermediate in the production of chemicals (dyes, pigments, pharmaceuticals)

Additional Use

Research chemical

Potential Applications

Organic synthesis

Toxicity

Known to be toxic if inhaled or ingested

Safety Precautions

Proper safety measures should be taken when handling the compound

Upstream product

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• 82302-27-0 8-chloro-3,4-dihydro-2(1H)-naphthalenone 
• 412041-50-0 1,2-diethynyl-4-methylbenzene 
• 331992-74-6 8-chloro-2-methyl-1,2,3,4-tetrahydronaphthalen-2-ol 
• 103859-80-9 1-methyl-4-(2,4,4,4-tetrachloro-butyl)-benzene 

Downstream Products

• 2304635-11-6 4,4,5,5-tetramethyl-2-(7-methylnaphthalen-1-yl)-1,3,2-dioxaborolane 
• 904922-97-0 8-chloronaphthalene-2-carboxaldehyde 

Relevant articles and documents

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.).

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.

Antihyperglycemic Activity of Novel Naphthalenyl 3H-1,2,3,5-Oxathiadiazole 2-Oxides

A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus.Substitution at the 1-,5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4--3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.