50337-75-2

Usage

Chemical structure

1-(tert-butoxy)naphthalene consists of a naphthalene core with a tert-butoxy group attached to it.

Functional groups

The compound has a naphthalene ring system and a tert-butoxy group.

Solvent properties

It is commonly used as a solvent due to its low toxicity and high solvency power.

Steric hindrance

The tert-butoxy group provides steric hindrance, making the compound more stable and less reactive.

Applications

It is often used in organic synthesis and as a component of specialty coatings, adhesives, and sealants.

Safety precautions

It is important to handle 1-(tert-butoxy)naphthalene with caution, as it can be harmful if it comes into contact with skin or if it is inhaled.

Environmental impact

It has the potential to cause environmental harm, so proper disposal and handling procedures should be followed.

Physical state

The compound is likely to be a liquid at room temperature, as it is a relatively non-polar molecule with a large molecular size.

Boiling point

The boiling point of 1-(tert-butoxy)naphthalene is not provided in the material, but it can be inferred that it would be higher than that of naphthalene due to the additional tert-butoxy group.

Density

The density of 1-(tert-butoxy)naphthalene is not provided in the material, but it can be expected to be higher than that of naphthalene due to the presence of the tert-butoxy group.

Viscosity

The viscosity of 1-(tert-butoxy)naphthalene is not provided in the material, but it can be expected to be higher than that of naphthalene due to the increased steric hindrance from the tert-butoxy group.

Flashpoint

The flashpoint of 1-(tert-butoxy)naphthalene is not provided in the material, but it can be expected to be higher than that of naphthalene due to the presence of the tert-butoxy group, which may reduce the compound's flammability.

Chemical stability

The compound is more stable than naphthalene due to the presence of the tert-butoxy group, which provides steric hindrance and reduces reactivity.

Reactivity

The reactivity of 1-(tert-butoxy)naphthalene is reduced compared to naphthalene due to the steric hindrance provided by the tert-butoxy group.

Compatibility

The compound is likely to be compatible with a range of organic solvents and materials, as it is used in organic synthesis and as a component of specialty coatings, adhesives, and sealants.

InChI:InChI=1/C14H16O/c1-14(2,3)15-13-10-6-8-11-7-4-5-9-12(11)13/h4-10H,1-3H3

Upstream product

• 614-45-9 tert-Butyl peroxybenzoate 
• 703-55-9 1-naphthylmagnesiumbromide 
• 90-15-3 α-naphthol 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 90-11-9 1-Bromonaphthalene 
• 865-48-5 sodium t-butanolate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 507-19-7 t-butyl bromide 
• 19616-28-5 2,2′4,4′-tetramethyldiphenylamine 

Relevant academic research and scientific papers

Synthesis of Sterically Congested Triarylamines by Palladium-Catalyzed Amination

An efficient protocol for the palladium-catalyzed synthesis of sterically congested triarylamines from commercially available 1-chloro- or 1-bromonaphthalenes and diarylamines is described. The application of alkyllithium reagents as strong bases and a combination of Pd(OAc)2 and SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) plays a crucial role in the success of this otherwise difficult to achieve C-N coupling reaction. A variety of secondary aromatic amines with versatile steric and electronic properties can be successfully used in this transformation to give the desired triarylamines in up to 99 % yield. The obtained products are important structural motifs in hole-transport materials for organic light-emitting diode applications.

A convenient synthesis of tert-butyl ethers under microwave condition

Synthesis of tert-butyl ethers from various alcohols and substituted phenols can be achieved using tert-butyl bromide in the presence of basic lead carbonate as a catalyst under microwave irradiation in absence of solvent. The catalyst is easily recovered via filtration and reused up to three times without appreciable loss of activity.

Efficient synthesis of tert-butyl ethers under solvent-free conditions

A simple and efficient synthesis of tert-butyl ethers from various alcohols and substituted phenols using tert-butyl bromide in the presence of basic lead carbonate as a catalyst. The catalyst is easily recovered via filtration and can be reused up to three times without appreciable loss of activity. Copyright Taylor & Francis Group, LLC.

Alcohols and di-tert-butyl dicarbonate: How the nature of the Lewis acid catalyst may address the reaction to the synthesis of tert-butyl ethers

The reaction between alcohols and Boc2O leads to the formation of ferf-butyl ethers and/or Boc-alcohols, depending on the nature of the Lewis acid catalyst. Product distribution is mainly tuned by the anionic part of the salt. Perchlorates and Inflates, anions with highly delocalized negative charge, give prevalent or exclusive ether formation. On the other hand, Boc alcohols are the main or exclusive products with un-delocalized isopropoxide or low-delocalized acetate ions. The metal ion influences only the reaction rate, roughly following standard parameters for calculating Lewis acidity. A reaction mechanism is supposed, and a series of experimental evidences is reported to support it. These studies allowed us to conclude that, to synthesize tert-butyl ethers, in reactions involving aliphatic alcohols, Mg(ClO4) 2 or Al(ClO4)3 represents the best compromise between costs and efficiency of the reaction, while, in reactions involving phenols, Sc(OTf)3 is the best choice, since aromatic tert-butyl ethers are not stable in the presence of perchlorates.

Unusual and unexpected reactivity of t-butyl dicarbonate (Boc2O) with alcohols in the presence of magnesium perchlorate. A new and general route to t-butyl ethers

(Chemical Equation Presented) A new mild method for protecting alcohols as t-butyl ethers is reported. The reaction proceeds with Mg(ClO4) 2 and Boc2O and shows general applicability. The deprotection of t-butyl ethers has also been revisited. Preliminary results indicate the CeCl3·7H2O/Nal system is a very suitable catalyst for their removal.

A NEW SYNTHETIC METHOD FOR THE PREPARATION OF TERT-BUTYL ARYL ETHERS

A facile synthesis for the preparation of tert-butyl aryl ethers from phenols under basic conditions is described.