16271-22-0

Basic information

• Product Name: 4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane
• Synonyms: 4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane
• CAS NO: 16271-22-0
• Molecular Weight: 284.398
• Mol File: 16271-22-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane(16271-22-0)
• EPA Substance Registry System: 4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane(16271-22-0)

Safety Data

• Hazardous Substances Data: 16271-22-0(Hazardous Substances Data)

Upstream product

• 5384-21-4 bis(4-hydroxy-3,5-dimethylphenyl)methane 
• 77-78-1 dimethyl sulfate 
• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 
• 74-95-3 1,1-dibromomethane 
• 1517-63-1 4-methylphenyl(phenyl)methanol 
• 1426391-61-8 bis(4-methoxy-3,5-dimethylphenyl)methanol 
• 885-77-8 4,4'-dimethylbenzhydrol 
• 1426391-39-0 [bis(4-methoxy-3,5-dimethylphenyl)]methyl (phenyl)(p-tolyl)methyl ether 
• 1426391-31-2 bis[bis(4-methoxy-3,5-dimethylphenyl)methyl] ether 
• 1426391-38-9 [bis(4-methoxy-3,5-dimethylphenyl)]methyl diphenylmethyl ether 
• 1426391-40-3 [bis(4-methoxy-3,5-dimethylphenyl)]methyl bis(p-tolyl)methyl ether 
• 74-88-4 methyl iodide 
• 83037-98-3 (4-methoxy-3,5-dimethylphenyl)methanol 
• 2233-18-3 4-hydroxy-3,5-dimethylbenzaldehyde 

Downstream Products

• 110047-35-3 4,4’-dimethoxy-3,3’,5,5’-dimethylbenzophenone 
• 16271-23-1 2,2'-Bis(chloromethyl)-4,4'-dimethoxy-3,3',5,5'-tetramethyldiphenylmethane 

Relevant articles and documents

Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media

We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.

Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I 2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel-Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C-H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.