6442-58-6

Basic information

• Product Name: Benzoic acid, 4-(cyclohexyloxy)-, methyl ester
• CAS NO: 6442-58-6
• Molecular Formula: C14H18O3
• Molecular Weight: 234.295
• Mol File: 6442-58-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(cyclohexyloxy)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(cyclohexyloxy)-, methyl ester(6442-58-6)
• EPA Substance Registry System: Benzoic acid, 4-(cyclohexyloxy)-, methyl ester(6442-58-6)

Safety Data

• Hazardous Substances Data: 6442-58-6(Hazardous Substances Data)

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 108-93-0 cyclohexanol 
• 110-83-8 cyclohexene 
• 619-42-1 4-methoxycarbonylphenyl bromide 

Downstream Products

• 139-61-7 4-(Cyclohexyloxy)benzoic acid 
• 36823-91-3 4-cyclohexyloxy-benzoyl chloride 

Relevant articles and documents

Synthesis, Antiproliferative and Antioxidant Activity of 3-Mercapto-1,2,4-Triazole Derivatives as Combretastatin A-4 Analogues

Two series of 3-mercapto-1,2,4-triazole derivatives containing alkoxy substituents different in size and position were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. The synthesized compounds were assessed for their antiproliferative activity against colon cancer cell line (SW480). The results indicated that the size and position of the alkoxy group significantly influenced the antiproliferative activity. The highest cancer cell growth inhibition values were observed for the compounds containing 3,4,5-trimethoxyphenyl groups in their structures (57.74, 54.14 and 60.70% at 50 μM for compounds 5a, 12b and 14, respectively). The synthesized compounds were also subjected to DPPH protocol for evaluating the antioxidant activity. The results showed that all compounds had moderate to high levels of antioxidant capacity as compared to ascorbic acid as standard, the highest free radical scavenging capacity of 75% was observed for compound 4a at 50 μM.

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.

Decarboxylative C(sp3)?O Cross-Coupling

Alkyl aryl ethers are an important class of compounds in medicinal and agricultural chemistry. Catalytic C(sp3)?O cross-coupling of alkyl electrophiles with phenols is an unexplored disconnection strategy to the synthesis of alkyl aryl ethers, with the potential to overcome some of the major limitations of existing methods such as C(sp2)?O cross-coupling and SN2 reactions. Reported here is a tandem photoredox and copper catalysis to achieve decarboxylative C(sp3)?O coupling of alkyl N-hydroxyphthalimide (NHPI) esters with phenols under mild reaction conditions. This method was used to synthesize a diverse set of alkyl aryl ethers using readily available alkyl carboxylic acids, including many natural products and drug molecules. Complementarity in scope and functional-group tolerance to existing methods was demonstrated.