5396-38-3

Basic information

• Product Name: 4-TERT-BUTYLANISOLE
• Synonyms: 1-(1,1-dimethylethyl)-4-methoxy-benzen;1-tert-Butyl-4-methoxybenzene;1-tert-Butyl-4-methoxy-benzene;4-tert-Butylphenyl methyl ether;Anisole, p-tert-butyl-;Benzene, 1-methoxy-4-t-butyl;p-Methoxy-tert-butylbenzene;4-Methoxy-tert-butylbenzene
• CAS NO: 5396-38-3
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24
• EINECS: 226-412-2
• Product Categories: Miscellaneous;Anisoles, Alkyloxy Compounds & Phenylacetates
• Mol File: 5396-38-3.mol
• Article Data: 60

Chemical Properties

• Melting Point: 18°C
• Boiling Point: 80°C 1,5mm
• Flash Point: 201 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.938 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.503(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2041952
• CAS DataBase Reference: 4-TERT-BUTYLANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLANISOLE(5396-38-3)
• EPA Substance Registry System: 4-TERT-BUTYLANISOLE(5396-38-3)

Safety Data

• Hazard Codes: Xi
• Statements: 11
• Safety Statements: 23-24/25
• RIDADR: 3271
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5396-38-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

4-tert-Butylanisole is used as a reactant in nucleophilic substitution of para-?substituted phenol ethers in the presence of a hypervalent iodine compound.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2826, 1971 DOI: 10.1021/ja00740a064

InChI:InChI=1/C20H12Cl2N2O2S2/c21-11-4-6-14-16(9-11)28-18(17(14)22)19(26)24-20(27)23-15-3-1-2-10-8-12(25)5-7-13(10)15/h1-9,25H,(H2,23,24,26,27)

Upstream product

• 13195-76-1 triisobutyl borate 
• 100-66-3 methoxybenzene 
• 507-20-0 tertiary butyl chloride 
• 33733-83-4 3-tert-butyl-1-methoxybenzene 
• 507-19-7 t-butyl bromide 
• 594-70-7 2-Methyl-2-nitropropane 
• 75-65-0 tert-butyl alcohol 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 402-52-8 methyl 4-(trifluoromethyl)phenyl ether 
• 75-24-1 trimethylaluminum 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 677-22-5 tert-butylmagnesium chloride 
• 66107-29-7 4-methoxyphenyl triflate 
• 67-56-1 methanol 

Downstream Products

• 854675-87-9 4-(5-tert-butyl-2-methoxy-phenyl)-4-oxo-butyric acid 
• 102162-08-3 5-tert-butyl-2-methoxy-4'-methyl-benzophenone 
• 77055-30-2 5-tert-butyl-2-methoxy-1,3-dinitrobenzene 
• 75908-79-1 5-tert-butyl-2,4'-dimethoxy-benzophenone 
• 69403-15-2 1,3-Bis(bromomethyl)-5-tert-butyl-2-methoxybenzene 
• 70605-60-6 C₂₄H₃₁Cl₃O₂ 
• 85943-26-6 5-tert-butyl-2-methoxybenzaldehyde 
• 98085-85-9 bis(5-tert-butyl-2-methoxyphenyl)methanone 
• 855225-81-9 4-(5-tert-butyl-2-methoxy-phenyl)-butyric acid 
• 98-54-4 para-tert-butylphenol 
• 114378-07-3 1-tert-Butyl-4-trimethylsilylmethylbenzene 
• 372511-75-6 4-tert-butyl-2,6-bis[(1-imidazolyl)methyl]anisole 

Relevant articles and documents

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents

Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].

Trialkylammonium salt degradation: Implications for methylation and cross-coupling

Trialkylammonium (most notably N,N,N-trimethylanilinium) salts are known to display dual reactivity through both the aryl group and the N-methyl groups. These salts have thus been widely applied in cross-coupling, aryl etherification, fluorine radiolabelling, phase-transfer catalysis, supramolecular recognition, polymer design, and (more recently) methylation. However, their application as electrophilic methylating reagents remains somewhat underexplored, and an understanding of their arylation versus methylation reactivities is lacking. This study presents a mechanistic degradation analysis of N,N,N-trimethylanilinium salts and highlights the implications for synthetic applications of this important class of salts. Kinetic degradation studies, in both solid and solution phases, have delivered insights into the physical and chemical parameters affecting anilinium salt stability. 1H NMR kinetic analysis of salt degradation has evidenced thermal degradation to methyl iodide and the parent aniline, consistent with a closed-shell SN2-centred degradative pathway, and methyl iodide being the key reactive species in applied methylation procedures. Furthermore, the effect of halide and non-nucleophilic counterions on salt degradation has been investigated, along with deuterium isotope and solvent effects. New mechanistic insights have enabled the investigation of the use of trimethylanilinium salts in O-methylation and in improved cross-coupling strategies. Finally, detailed computational studies have helped highlight limitations in the current state-of-the-art of solvation modelling of reaction in which the bulk medium undergoes experimentally observable changes over the reaction timecourse. This journal is