726-94-3

Basic information

• Product Name: 1-(4-methoxyphenyl)adamantane
• Synonyms: 1-(4-methoxyphenyl)adamantane
• CAS NO: 726-94-3
• Molecular Weight: 242.361
• Mol File: 726-94-3.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-methoxyphenyl)adamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxyphenyl)adamantane(726-94-3)
• EPA Substance Registry System: 1-(4-methoxyphenyl)adamantane(726-94-3)

Safety Data

• Hazardous Substances Data: 726-94-3(Hazardous Substances Data)

Upstream product

• 768-90-1 1-Adamantyl bromide 
• 100-66-3 methoxybenzene 
• 32314-61-7 1-nitroxyadamantane 
• 696-62-8 para-iodoanisole 
• 768-95-6 1-adamanthanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 57680-77-0 adamantylmagnesium bromide 
• 768-92-3 1-adamantyl fluoride 
• 184298-19-9 (S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-methyl-butyric acid adamantan-1-yl ester 

Downstream Products

• 1373443-03-8 (E)-3-[3-(4-adamantan-1-yl-phenoxy)-acryloylamino]-benzoic acid methyl ester 
• 1373443-30-1 (E)-3-(4-adamantan-1-yl-phenoxy)-acrylic acid 
• 1373443-26-5 (E)-3-(4-adamantan-1-yl-phenoxy)-acrylic acid methyl ester 
• 29799-07-3 4-adamantylphenol 

Relevant articles and documents

Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer

The construction of quaternary centers is a common challenge in the synthesis of complex materials and natural products. Current cross-coupling strategies that can be generalized for setting these centers are sparse and, when known, are typically predicated on the use of reactive organometallic reagents. To address this shortcoming a new, photoredox-Ni dual catalytic strategy for the cross-coupling of tertiary organoboron reagents with aryl halides is reported. In addition to details on the cross-coupling scope and limitations, full screening efforts and mechanistic experiments are communicated.

Flow Friedel–Crafts alkylation of 1-adamantanol with arenes using HO-SAS as an immobilized acid catalyst

In this communication flow Friedel–Crafts alkylation was studied using hydroxy-substituted sulfonic acid-functionalized silica as a catalyst and 1-adamantanol as a model substrate. The reaction of 1-adamantanol (1a) with toluene (2a) proceeded well with 5 min of residence time at 120°C to give good yield of 1-tolyladamantane (3a) as a 1:9 mixture of meta and para isomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3a in 97–92% yields, suggesting the durability of the catalyst.

Alkylation of aromatic compounds with 1-bromoadamantane in the presence of metal complex catalysts

Synthesis of aryladamantanes was performed by reaction of 1-bromoadamantane with aromatic compounds in the presence of metal complex catalysts containing Mo, Cr, W, Cu, and Co.

Phenoxyacrylic derivatives and use thereof

The present invention relates to a phenoxyacrylic derivative and a pharmaceutical composition comprising the same as an active ingredient for preventing or treating a nonalcoholic fatty liver disease. The compound according to the present invention has an

Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization

Synthesis of functionalized adamantanes from fluoroadamantanes

Selective introduction of functional groups on the tert-carbon of adamantane was performed by substitution with fluorides. A methyl, phenacyl, aryl, cyclohexyl, alkoxy, or azido group was introduced into the adamantane skeleton without influencing the oth

Triflic acid-catalyzed adamantylation of aromatics in [BMIM][OTf] ionic liquid; synthetic scope and mechanistic insight

A mild and efficient process has been developed for the one-pot adamantylation of aromatic substrates employing 1-AdaOH, 1-AdaCl, 1-AdaBr, and 1-Br-3,5,7-trimethyladamantane as adamantylating agents, with triflic acid (TfOH) as promoter and n-butylmethylimidazolium triflate [BMIM][OTf] room temperature ionic liquid (IL) as solvent. The influence of reaction temperature, reaction time and the amount of TfOH was gauged in model reactions employing 1-AdaOH, 1-AdaCl and 1-AdaBr with toluene as the substrate. Under optimal conditions, the reactions exhibit high para selectivity with little or no adamantane side-product being formed. The synthetic scope of this transformation was tested for representative alkylbenzenes and haloalkylbenzenes. Comparative reactions carried out in 1,2-dichloroethane (DCE) produce increased amounts of the meta isomer and substantial amounts of adamantane. Substrate selectivities (KT/KB) were measured in competitive experiments in [BMIM][OTf] and in DCE as solvents. Isomerization tests were performed to shed light on the origin of the meta isomer. A DFT study was also conducted to compare relative stabilities of the isomeric products, to gauge the relative stabilities of the intermediate isomeric benzenium ions of adamantylation and their charge distribution modes, and to explore the intramolecular process for isomerization in the benzenium ion. The Royal Society of Chemistry 2005.

1-adamantyl chalcones for the treatment of proliferative disorders

The present invention relates to the compounds of the general formula (I), a composition for and a method of treating breast cancer or other proliferative disorders in a subject using a compound of general formula [I], wherein the substituents are as defi

Palladium-Catalyzed Coupling Reactions of 1-Bromoadamantane with Styrenes and Arenes

The palladium-catalyzed reaction of 1-bromoadamantane (1-Br) with styrene and donor-substituted styrenes gave the corresponding Heck-type coupling products 3a and b, and 5a and b in moderate yields (15-41percent), while the reaction of 1-Br with various arenes 6a-p under palladium catalysis gave the corresponding adamantyl-substituted arenes 7a-p in good to excellent yields (35-98percent). - Keywords: cross-coupling reactions; metal-catalyzed/adamantylation of styrene and alkenes/arylation of 1-bromoadamantane/Heck reaction; palladium catalysis