17556-19-3

Basic information

• Product Name: 5-Chloro-2-tetralone
• Synonyms: 7-CHLORO-3,4-DIHYDRO-1H-NAPHTHALEN-2-ONE;7-Chloro-2-tetralone;5-Chloro-2-tetralone;5-Chloro-3,4-dihydronaphthalen-2(1H)-one;7-chloro-1,2,3,4-tetrahydronaphthalene-2-one;7-chloro-1,2,3,4-tetrahydronaphthalen-2-one;7-chloro-3,4-dihydronaphthalen-2(1H)-one;7-Chloro-2-tertralone
• CAS NO: 17556-19-3
• Molecular Formula: C₁₀H₉ClO
• Molecular Weight: 180.63
• Mol File: 17556-19-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 304.612 °C at 760 mmHg
• Flash Point: 145.219 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 0.00166mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 5-Chloro-2-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-tetralone(17556-19-3)
• EPA Substance Registry System: 5-Chloro-2-tetralone(17556-19-3)

Safety Data

• Hazardous Substances Data: 17556-19-3(Hazardous Substances Data)

Usage

General Description

5-Chloro-2-tetralone is a chemical compound with the molecular formula C10H9ClO. It belongs to the class of organic compounds known as tetralones, which are cyclic ketones that contain a 6-membered aliphatic ring. The presence of a chlorine atom at the 5th position of the tetralone ring gives this compound its unique properties. 5-Chloro-2-tetralone is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in organic synthesis and as a building block for the preparation of various other chemical compounds. Its versatile nature and reactivity make it a valuable tool in chemical research and development.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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

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.

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.