19578-74-6

Basic information

• Product Name: Benzene, 1,3-dimethyl-2-(phenylmethoxy)-
• CAS NO: 19578-74-6
• Molecular Formula: C15H16O
• Molecular Weight: 212.291
• Mol File: 19578-74-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzene, 1,3-dimethyl-2-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,3-dimethyl-2-(phenylmethoxy)-(19578-74-6)
• EPA Substance Registry System: Benzene, 1,3-dimethyl-2-(phenylmethoxy)-(19578-74-6)

Safety Data

• Hazardous Substances Data: 19578-74-6(Hazardous Substances Data)

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 100-39-0 benzyl bromide 
• 16081-16-6 sodium 2,6-dimethylphenolate 
• 100-44-7 benzyl chloride 
• 60-29-7 diethyl ether 
• 1004-66-6 2-methoxy-1,3-dimethylbenzene 
• 6711-19-9 benzylium cation 
• 53772-44-4 benzyloxydiphenylphosphine 
• 95414-83-8 benzyl 2,6-dimethylphenyl carbonate 
• 13326-10-8 benzyl methyl carbonate 
• 533-58-4 2-Iodophenol 
• 142523-69-1 1-benzyloxy-2-iodobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 42790-42-1 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride 

Downstream Products

• 576-26-1 2.6-dimethylphenol 
• 108-88-3 toluene 
• 41772-31-0 4‐benzyl‐2,6‐dimethylphenol 

Relevant articles and documents

Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents

Alkyl-substituted Li-phenolates with BnBr in water solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p ratio up to 90/1.

Ring-opening reactions of 1,4-diazabicyclo[2.2.2]octane (DABCO) derived quaternary ammonium salts with phenols and related nucleophiles

1,4-Diazabicyclo[2.2.2]octane (DABCO) has been evaluated as a starting material for the synthesis of 1-alkyl-4-(2-phenoxyethyl)piperazines and related derivatives. We found that 1-alkyl-1,4-diazabicyclo[2.2.2]octan-1-ium salts, resulting from the alkylation of DABCO, efficiently react with a variety of nucleophiles in polyethyleneglycol (PEG) or diglyme at high temperatures to give piperazine products resulting from the nucleophilic ring-opening reaction. The benzylation side reaction was found to be relevant with softer nucleophiles when using 1-benzyl-1,4-diazabicyclo[2.2.2]octan-1-ium salts, while other types of alkylations were not observed. One-pot methodologies allow for the synthesis of piperazines directly from primary alcohols, alkyl halides or sulfonates, using phenols, or other nucleophile sources, and DABCO. The Royal Society of Chemistry 2012.

Efficient methods for the preparation of alkyl-aryl and symmetrical or unsymmetrical dialkyl ethers between alcohols and phenols or two alcohols by oxidation-reduction condensation

Oxidation-reduction condensation via alkoxydiphenylphosphines (diphenylphosphinite esters) (1), generated in situ from chlorodiphenylphosphine (2) and alcohols, 2,6-dimethyl-1,4-benzoquinone (3), and phenols proceeds smoothly to afford alkyl-aryl ethers in good to high yields under neutral conditions. In a similar fashion, a new and efficient method for the preparation of symmetrical or unsymmetrical dialkyl ethers in good to high yields is established via tetrafluoro-1,4-benzoquinone (fluoranil) (4), alcohols, and 1 formed in situ from nBuLi-treated alcohols and 2. This method is applicable also to the etherification of chiral secondary or tertiary alcohols with retention or inversion of configurations. The inverted ethers are afforded by treating chiral alkoxydiphenylphosphines and achiral alcohols, while the reaction of achiral alkoxydiphenylphosphines and chiral alcohols forms retained ethers.