6669-13-2

Basic information

• Product Name: Phenyl-t-butylether
• Synonyms: (1,1-Dimethylethoxy)benzene;tert-Butyl phenyl ether, 98%;2-Methyl-2-phenoxypropane;Phenyl tert-butyl ether;tert-Butoxybenzene;Benzene, (1,1-dimethylethoxy)-;Inchi=1/C10H14o/C1-10(2,3)11-9-7-5-4-6-8-9/H4-8H,1-3h;NSC 78717
• CAS NO: 6669-13-2
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Mol File: 6669-13-2.mol
• Article Data: 44

Chemical Properties

• Melting Point: -17--16℃
• Boiling Point: 184°C
• Flash Point: 184°C
• Appearance: /
• Density: 0.924
• Vapor Pressure: 0.953mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Phenyl-t-butylether(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl-t-butylether(6669-13-2)
• EPA Substance Registry System: Phenyl-t-butylether(6669-13-2)

Safety Data

• Hazardous Substances Data: 6669-13-2(Hazardous Substances Data)

Usage

Description

Phenyl-t-butylether, also known as tert-butoxybenzene, is an organic compound that is commonly used in various industrial applications due to its unique chemical properties. It is characterized by its ability to form stable ethers and has a significant role in the synthesis of various compounds.

Uses

Used in Food Industry:
Phenyl-t-butylether is used as an additive for the enhancement of color and flavor in the production of northern air-dried sausage. It contributes to the improvement of the overall quality of the final product by influencing the characteristics of different starter cultures used in the process.
Please note that the provided materials only mention the use of Phenyl-t-butylether in the food industry, specifically in the analysis of color and flavor improvement in northern air-dried sausage. If there are other applications in different industries, they are not mentioned in the provided materials.

Synthesis

A 4-mL vial was charged with bromobenzene (63 mg, 0.40 mmol), Pd(dba)2 (11.5 mg, 0.0200 mmol), Ph5FcP-(t-Bu)2 (14.2 mg, 0.0200 mmol), and sodium tert-butoxide (47 mg, 0.48 mmol). Anhydrous toluene (2 mL) was added, and the vial was sealed with a cap containing a PTFE septum and removed from the dry box. The reaction mixture was stirred at room temperature for 23 h. The reaction solution was then adsorbed onto silica gel, and the product was isolated by eluting with EtOAc/hexanes (0 to 10% gradient) to give the ether (58 mg, 97%). Reference: Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553–5566.

InChI:InChI=1/C10H14O/c1-10(2,3)11-9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 614-45-9 tert-Butyl peroxybenzoate 
• 507-20-0 tertiary butyl chloride 
• 108-95-2 phenol 
• 507-19-7 t-butyl bromide 
• 558-17-8 tert-Butyl iodide 
• 75-65-0 tert-butyl alcohol 
• 110-86-1 pyridine 
• 108-86-1 bromobenzene 
• 865-47-4 potassium tert-butylate 
• 290-37-9 1,4-pyrazine 
• 123-31-9 hydroquinone 
• 591-50-4 iodobenzene 
• 107-71-1 tert-butyl peroxyacetate 
• 841-76-9 triphenylaluminium 

Downstream Products

• 98-54-4 para-tert-butylphenol 
• 88-18-6 2-tert-Butylphenol 
• 18995-35-2 4-tert-butoxychlorobenzene 
• 128-39-2 2,6-di-tert-butylphenol 
• 3233-32-7 hydroquinone monoacetate 
• 10357-72-9 p-tert-Butoxytriphenylmethan 
• 127517-27-5 2-(tert-butoxy)aniline 
• 57120-36-2 4-(tert-butoxy)aniline 
• 1415244-20-0 2-tert-butoxybenzophenone 
• 85417-72-7 Brenzcatechin-di-tert.-butylether 
• 23010-10-8 t-butyl pyrocatechol 
• 1415244-31-3 (3-tert-butoxy-2-hydroxyphenyl)diphenylphosphine 
• 1415244-29-9 o-tert-butoxy-cyclohexyloxybenzene 

Relevant articles and documents

Vapor-phase alkylation of phenol with tert-butyl alcohol catalyzed by H3PO4/MCM-41

The catalytic performance of Al-MCM-41 containing 5-35 wt H 3PO4 was studied for the vapor-phase alkylation of phenol with tert-butyl alcohol (TBA) from 383 to 493 K. 4-Tert-butyl phenol was produced as the main product with moderate selectivity. The product distribution depends on the reaction temperature, number of acid sites, and the Broensted to Lewis sites ratios. A lower molar ratio of reactants (TBA/phenol = 2) and a higher space velocity facilitated the production of 4-tert-butyl phenol. The influence of various parameters such as temperature, reactant feed molar ratio, feed rate, and time on stream were investigated for conversion yield and product selectivity.

Alkylation of Phenol with tert-Butanol in a Draining-Film Reactor

The alkylation of phenol with tert-butanol in a displacement draining-film reactor on a heterogeneous catalyst, Beta zeolite, was evaluated. Optimum process conditions ensuring the maximal p-tert-butylphenol yield were determined: phenol:tert-butanol molar ratio (3–3.5):1, superficial liquid velocity 1.0–1.5 m3 m–2 h–1, and temperature 100°C–110°C. A procedure ensuring 100% conversion of tert-butanol and isobutylene (a by-product formed from tert-butanol) was observed.

A study of diketopiperazines as electron-donor initiators in transition metal-free haloarene-arene coupling

Several diketopiperazines have been shown to promote carbon-carbon coupling between benzene and aryl halides in the presence of potassium tert-butoxide and without the assistance of a transition metal catalyst. The structure of the diketopiperazine has an influence on its reductive potential and can help to promote the coupling of the more challenging aryl bromides with benzene.

Cleavage of the lignin β-O-4 ether bond: Via a dehydroxylation-hydrogenation strategy over a NiMo sulfide catalyst

The efficient cleavage of lignin β-O-4 ether bonds to produce aromatics is a challenging and attractive topic. Recently a growing number of studies have revealed that the initial oxidation of CαHOH to CαO can decrease the β-O-4 bond dissociation energy (BDE) from 274.0 kJ mol-1 to 227.8 kJ mol-1, and thus the β-O-4 bond is more readily cleaved in the subsequent transfer hydrogenation, or acidolysis. Here we show that the first reaction step, except in the above-mentioned pre-oxidation methods, can be a Cα-OH bond dehydroxylation to form a radical intermediate on the acid-redox site of a NiMo sulfide catalyst. The formation of a Cα radical greatly decreases the Cβ-OPh BDE from 274.0 kJ mol-1 to 66.9 kJ mol-1 thereby facilitating its cleavage to styrene, phenols and ethers with H2 and an alcohol solvent. This is supported by control experiments using several reaction intermediates as reactants, analysis of product generation and by radical trap with TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) as well as by density functional theory (DFT) calculations. The dehydroxylation-hydrogenation reaction is conducted under non-oxidative conditions, which are beneficial for stabilizing phenol products.