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

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.

Uses

tert-Butoxybenzene was studied in the analysis of the color and flavor improvement of different starter cultures on northern air-dried sausage.

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

Upstream product

• 115-11-7 isobutene 
• 108-95-2 phenol 
• 75-65-0 tert-butyl alcohol 
• 93-99-2 benzoic acid phenyl ester 
• 19252-54-1 isobutyl cation 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 507-20-0 tertiary butyl chloride 
• 507-19-7 t-butyl bromide 
• 558-17-8 tert-Butyl iodide 
• 100-02-7 4-nitro-phenol 
• 151484-28-5 1,1-dimethylethyl diphenylphosphinite 
• 865-48-5 sodium t-butanolate 
• 105242-73-7 1,1,1-triphenyl-2,1λ(5)-benzoxabismol-3(1H)-one 
• 123-31-9 hydroquinone 

Downstream Products

• 85599-10-6 C₂₀H₂₇O₃P 
• 18995-35-2 4-tert-butoxychlorobenzene 
• 60876-70-2 4-tert-butoxybromobenzene 
• 98-54-4 para-tert-butylphenol 
• 88-18-6 2-tert-Butylphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 108-95-2 phenol 
• 68314-56-7 2,2'-(P,P'-dioxo-P,P'-diphenyl-P,P'-ethane-1,2-diyl-bis-λ⁵-phosphanyl)-bis-phenol 
• 85599-05-9 (o-hydroxyphenyl)phenylphosphineoxide 
• 85599-09-3 C₁₂H₁₁O₃P 
• 85599-18-4 C₃₄H₄₀O₂P₂ 
• 344415-07-2 C₃₄H₄₀O₄P₂ 
• 128-39-2 2,6-di-tert-butylphenol 
• 127517-27-5 2-(tert-butoxy)aniline 

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.

Singlet vs Triplet Reactivity of Photogenerated α,n-Didehydrotoluenes

The reactivity of α,n-didehydrotoluenes (DHTs) in protic media (organic/aqueous mixtures) was explored by means of a combined computational and experimental approach. These intermediates were generated via a photoinduced double elimination process occurring in (chlorobenzyl)trimethylsilanes and led to the formation of a varied products distribution, depending on the isomer tested. Irradiation of ortho- and para-derivatives resulted, respectively, in the formation of triplet α,2- and α,4-DHTs, whose diradical reactivity led to both radical and polar products. On the other hand, irradiation of the meta-precursor led to the singlet α,3-DHT isomer. The latter showed a marked preference for the formation of polar products and this was rationalized, as supported by computational evidence, via the involvement of a zwitterionic species arising through interaction of the nucleophilic solvent with the benzylic position of the DHT.

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.