22165-05-5

Basic information

• Product Name: 4-methoxy-1-tetradecylbenzene
• Synonyms: 4-methoxy-1-tetradecylbenzene
• CAS NO: 22165-05-5
• Molecular Weight: 304.516
• Mol File: 22165-05-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-methoxy-1-tetradecylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-1-tetradecylbenzene(22165-05-5)
• EPA Substance Registry System: 4-methoxy-1-tetradecylbenzene(22165-05-5)

Safety Data

• Hazardous Substances Data: 22165-05-5(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 19218-94-1 1-iodotetradecane 
• 112-71-0 1-Bromotetradecane 
• 10374-74-0 tetradec-7-ene 
• 696-62-8 para-iodoanisole 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 110220-87-6 n-tetradecylmagnesium chloride 
• 112-64-1 tetradecanoyl chloride 
• 100-66-3 methoxybenzene 
• 102456-30-4 1-(4-methoxy-phenyl)-tetradecan-1-one 

Downstream Products

• 90857-80-0 3-(4-tetradecylphenoxy)-1,2-propanediol 
• 90857-81-1 3-(3-tetradecylphenoxy)-1,2-propanediol 
• 90857-77-5 2,2-dimethyl-4-<(4-tetradecylphenoxy)methyl>-1,3-dioxolane 
• 90857-84-4 1-[(4-methoxyphenyl)diphenylmethoxy]-3-(3-tetradecylphenoxy)-2-propanol 
• 90857-98-0 1-hydroxy-3-(3-tetradecylphenoxy)propan-2-yl acetate 
• 90857-88-8 2-(phenylmethoxy)-3-(4-tetradecylphenoxy)-1-propanol 
• 90857-99-1 2-bromoethyl 2-(acetyloxy)-3-(3-tetradecylphenoxy)propyl phosphate 
• 90857-94-6 2-<phosphinyl>oxy>-N,N,N-trimethylethanaminium, hydroxide, inner salt 
• 90857-90-2 2-bromoethyl 2-(phenylmethoxy)-3-(4-tetradecylphenoxy)propyl phosphate 
• 90857-83-3 1-(4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol 
• 90858-00-7 4-hydroxy-N,N,N-trimethyl-9-oxo-7-[(3-tetradecylphenoxy)methyl]-3,5,8-trioxa-4-phosphadecan-1-aminium 4-oxide, hydroxide, inner salt 
• 90857-96-8 4-hydroxy-N,N,N-trimethyl-9-oxo-7-[(4-tetradecylphenoxy)methyl]-3,5,8-trioxa-4-phosphadecan-1-aminium 4-oxide, hydroxide, inner salt 
• 90857-92-4 4-hydroxy-N,N,N-trimethyl-9-phenyl-7-<(2-tetradecylphenoxy)methyl>-3,5,8-trioxa-4-phosphanonan-1-aminium 4-oxide, hydroxide, inner salt 
• 90857-86-6 1-<2-(phenylmethoxy)-3-(triphenylmethoxy)propoxyl>-4-tetradecylbenzene 

Relevant articles and documents

Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes

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Nickel-Catalyzed C(sp2)?C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents

Aryl tosylates are an attractive class of electrophiles for cross-coupling reactions due to ease of synthesis, low price, and the employment of C?O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni-catalyzed C(sp2)?C(sp3) Kumada cross-coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross-coupling with challenging alkyl organometallics possessing β-hydrogens that are prone to β-hydride elimination and homo-coupling. The reaction is catalyzed by an air- and moisture stable-Ni(II) precatalyst. A broad range of electronically-varied aryl tosylates, including bis-tosylates, underwent this transformation, and many examples are suitable at mild room temperature conditions. The combination of Ar?X cross-coupling with the facile Ar?OH activation/cross-coupling strategy permits for orthogonal cross-coupling with challenging alkyl organometallics. Furthermore, we demonstrate that the method operates with TON reaching 2000, which is one of the highest turnovers observed to date in Ni-catalyzed cross-couplings. (Figure presented.).

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