17556-19-3

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Chloro-2-tetralone is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity allow for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Production:
In the agrochemical industry, 5-Chloro-2-tetralone serves as a key intermediate for the production of various agrochemicals. Its role in the synthesis of these compounds helps in the development of effective solutions for agricultural applications, such as pest control and crop protection.
Used in Organic Synthesis:
5-Chloro-2-tetralone is employed as a building block in organic synthesis, enabling the preparation of a diverse array of chemical compounds. Its unique properties and reactivity make it a useful component in the creation of complex organic molecules for various applications.
Used in Chemical Research and Development:
As a versatile and reactive compound, 5-Chloro-2-tetralone is a valuable tool in chemical research and development. It is used to explore new chemical reactions, develop innovative synthetic pathways, and enhance the understanding of chemical processes and mechanisms.

InChI:InChI=1/C9H7ClO/c10-9-3-1-2-6-4-7(11)5-8(6)9/h1-3H,4-5H2

Upstream product

• 74-85-1 ethene 
• 41904-39-6 3-chloro-benzeneacetyl chloride 
• 1160858-19-4 C₁₂H₁₃ClO₄ 
• 1190847-98-3 C₁₄H₂₁ClO₃ 
• 1878-65-5 3-chlorophenylacetic acid 

Downstream Products

• 150256-11-4 2-chloro-7-methylnaphthalene 
• 620171-74-6 1-benzyl-7-chloro-3,4-dihydro-1H-naphthalen-2-one 

Relevant academic research and scientific papers

A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal

4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tande

TiCl4-promoted intramolecular cyclization of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones: an expedient method to prepare 2-tetralones

DABCO is a very effective catalyst in the formation of 4-methoxy-5-arylethyl-1,3-dioxolan-2-ones 12 from the corresponding α-carbonatoaldehyde. Intramolecular cyclization of cyclic carbonates 12 promoted by TiCl4 affords 2-tetralones 13 contain

Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

We report on a series of α-substituted-β-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described.

The synthesis of novel cis-α-substituted-β-aminotetralins

Teteralones were converted, in 1 to 3 steps, to α-substituted tetralones. Subsequent reductive amination with ammonium acetate/sodium cyanoborohydride gave the corresponding α-substituted-β-aminotetralins, on a multigram scale, with minimal chromatography for the entire transformation.

Electronic effects on enol acidity and keto-enol equilibrium constants for ring-substituted 2-tetralones

Equilibrium constants for the ionization of a variety of phenyl-substituted 2-tetralones (pK(a)(K)), for the ionization of their enols (pK(a)(E)), and for keto-enol tautomerization (PK(E)) were determined. Hammett plots of pK(a)(K) and pK(a)(E) vs. σ are linear with slopes (-ρ) of -1.66 ± 0.06 and -0.90 ± 0.03, respectively, except for deviations of the points corresponding to 6-nitro-2-tetralone (1b) and its enol. We have previously attributed the negative deviation of 1b from the correlation for the acidities of the ketones obtained with the more limited set of data to the lack of a free electron pair on C-1 of the free tetralone (Nevy et al.). The negative deviation of the point for 1b from the correlation for the acidities of the enols suggests that charge transfer from the hydroxyl group of the enol to the nitro group is less important than it is for phenols. This study represents the first systematic study of electronic effects on equilibria among ketone, enol, and enolate in aqueous solution.

Transition state imbalance in proton transfer from phenyl ring-substituted 2-tetralones to acetate ion

Rate constants for the acetate ion-catalyzed ketonization of phenyl-substituted 2-tetralone enols have been determined by stopped-flow UV spectroscopy. From these rate constants and the keto - enol equilibrium constants, the rate constants (k-2) for enolization were calculated. A Bronsted plot of these rate constants (log k-2) vs the acidity of the appropriate 2-tetralone (pKaK) is linear, with a slope ( - αE) of - 0.78 ± 0.03, except for the point corresponding to 6-nitro-2-tetralone (4b). Rate constants for the ionization of 2-tetralone by substituted acetates were determined directly by NMR, giving a corresponding Bronsted βE of 0.54 ± 0.03. Both the negative deviation of the point for 4b from the correlation line for αE and the inequality between αE and βE indicate an imbalanced transition state for the proton abstraction of 2-tetralone by acetate ion. This reaction is impeded by a thermodynamic barrier of 11 kcal/mol, along with an intrinsic kinetic barrier of 14 kcal/mol. A comparison of the transition states for proton abstraction of 2-tetralone by hydroxide ion and by acetate ion shows similar transition state imbalance and intrinsic kinetic barriers for both reactions. The relevance of these results to the mechanism of enzymatic acceleration of enolization is discussed.

Bicyclic amine derivatives and their use as anti-psychotic agents

This invention relates to compounds of formula (I) STR1 which are useful as modulators of D3 receptors, in particular as antipsychotic agents.

Transition state imbalance in the deprotonation of substituted 2- tetralones by hydroxide ion

Rate and equilibrium constants for the deprotonation of a series of phenyl-substituted 2-tetralones in aqueous sodium hydroxide have been determined. A Bronsted plot of log k for deprotonation vs pK(a) of the appropriate 2-tetralone is linear with a slope (-α) of -0.60 ± 0.01, except for the point corresponding to 6-nitro-2-tetralone (1b). The negative deviation of 1b from the correlation indicates that the transition state for deprotonation of 2-tetralone is imbalanced, with delocalization of charge into the phenyl ring lagging behind proton transfer. A semiquantitative assessment of the charge distribution in both the fully formed anion and the transition state for deprotonation was calculated from these results and 13C NMR spectra of the 2-tetralone anion in methanol/water mixtures. Although approximately twice as much negative charge is localized on the oxygen than on the enolate carbon in the anion, slightly more charge is on the enolate carbon in the transition state.

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.

5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydrophthalenes: Centrally acting DA and 5-HT(1A) agonists

5-, 6-, 7- and 8-Amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene were synthesized and compared with the corresponding phenolic compounds in vivo and in vitro for their effects on central serotonergic (5-HT(1A)) and dopaminergic (D2) systems. The 5- and 8-amino isomers surprisingly showed a 100-fold lower affinity for D2 and 5-HT(1A) receptors, respectively, than their corresponding phenols. This was also reflected in vivo. The 6-amino- and hydroxy-isomers were equipotent, while the 7-amino compound showed in vivo effects both on dopaminergic and serotonergic systems, the latter not being noticed in vitro. Intermediates 8-bromo-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene and 2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid methyl ester were also tested and found to be quite potent 5-HT(1A) agonists.