58485-68-0

Usage

Type of compound

Organic compound

Structure

Contains a chlorine atom attached to a tetrahydronaphthalene ring

Usage

Building block in the synthesis of various organic compounds

Applications

Used in the production of pesticides, pharmaceuticals, and other industrial products

Physical state

Flammable liquid

Odor

Slightly sweet

Hazardous nature

Considered a hazardous material that should be handled with care

Occurrence

Not commonly found in nature

Production

Primarily produced through chemical synthesis in laboratory settings

Upstream product

• 119-64-2 tetralin 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 

Downstream Products

• 280552-77-4 1-[bis(4-methoxyphenyl)methylidenyl]-1,2,3,4-tetrahydronaphthalene 
• 150313-56-7 C₂₃H₂₀O₂ 
• 187221-31-4 (+/-)-1-(1,2,3,4-tetrahydronaphth-1-yl)piperazine 
• 228255-84-3 1-methyl-4-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine 
• 1914-65-4 tetralin-1-carboxylic acid 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 
• 132205-64-2 1-cyanotetraline 
• 93877-52-2 Phenyl-<1,2,3,4-tetrahydro-naphthyl-(1)>-essigsaeure 
• 93809-53-1 Phenyl-<1,2,3,4-tetrahydro-naphthyl-(1)>-acetylchlorid 
• 94378-06-0 Phenyl<1,2,3,4-tetrahydro-naphthyl-(1)>acetyldiazomethan 
• 125364-41-2 1-(4-Phenoxybutyl)-1-tetralincarbonsaeureamid 

Relevant academic research and scientific papers

Thiourea-Mediated Halogenation of Alcohols

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

Silica Chloride (SiO2-Cl), a New Heterogeneous Reagent, for the Selective and Efficient Conversion of Benzylic Alcohols to Their Corresponding Chlorides and Iodides

Structurally different benzylic alcohols were efficiently converted to their corresponding chlorides by silica chloride (SiO2-Cl) in CHCl3 at room temperature. Silica chloride is also able to convert benzylic alcohols to their iodides in the presence of NaI in a mixture of CH3CN/CHCl3 in excellent yields.

The Regio- and Stereoselectivity of Radical Chlorination of Cycloalkanes with Different Halogen Carriers and Host-Guest Complexes

The reaction of trans-1,4-dimethylcyclohexane (1) with (dichloroiodo)benzene (D), with most of the p-substituted D-derivatives, and with chlorine in carbon disulfide shows a regioselectivity of Rts ca. 10; reactions with o-substituted D-compounds or with D (R=H) in acetic acid or water show appreciable conversion, but lower selectivities of Rts ca. 5.Tertiary cyclohexyl radicals are chlorinated preferentially from the axial side with D (R=H); ortho-substituents in D, or replacement of CCl4 by CS2 or benzene lead to lower stereoselectivities.Chlorinations with iodophenyl derivatives, which are bound to a steroid matrix, exhibit no significant change in regioselectivity; the same is observed for reactions with chlorine in the presence of newly synthesized macrocyclic azacyclophane salts in water, although these form inclusion complexes with the hydrocarbons used and inhibit the hydrolysis of chlorides obtained from tetralin. α-Cyclodextrin, however, leads by selective complexation of 1 to selective chlorination of the primary C-H bonds.Syntheses and 13C NMR shifts of the azacyclophanes are described.