22792-02-5

Upstream product

• 1014-66-0 trimethyl(4-nitrophenoxy)silane 
• 38841-98-4 n-octylmagnesium chloride 
• 629-05-0 n-octyne 
• 123-30-8 4-amino-phenol 
• 111-86-4 n-Octylamine 
• 106-48-9 4-chloro-phenol 
• 538-23-8 tricaprilin 
• 124-13-0 Octanal 

Relevant academic research and scientific papers

Anti-Markovnikov Addition of Anilines to Aliphatic Terminal Alkynes Catalyzed by an 8-Quinolinolato Rhodium Complex

Anti-Markovnikov addition of anilines to aliphatic terminal alkynes proceeded using an 8-quinolinolato rhodium/phosphine catalyst system. The use of a strong organic base, 1,1,3,3,–tetramethylguanidine, in the catalyst system enabled the formation of the aldimine products. Substrates with various functional groups including polar groups such as a phenolic hydroxy group are applicable to the hydroamination.

Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines

Triglycerides are used for the direct N-alkylation of amines with molecular hydrogen for the first time. A broad range of interesting and industrially relevant secondary and tertiary amines are obtained in the presence of an in situ formed Ru/Triphos complex. Notably, plant oil can be efficiently applied in this single-step process. Moreover, a variety of other methyl esters can be used as N-alkylation agents in the presence of hydrogen for the synthesis of more advanced building blocks.

Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: Scope and structure-activity relationships

We describe a systematic study of the scope and relationship between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alkylphosphines for the amination of heteroaryl and aryl chlorides, bromides, and iodides. In the presence of this catalyst, aryl and heteroaryl chlorides, bromides, and iodides react with many primary amines in high yields with part-per-million quantities of palladium precursor and ligand. Many reactions of primary amines with both heteroaryl and aryl chlorides, bromides, and iodides occur to completion with 0.0005-0.05 mol % catalyst. A comparison of the reactivity of this catalyst for the coupling of primary amines at these loadings is made with catalysts generated from hindered monophosphines and carbenes, and these data illustrate the benefits of chelation. Studies on structural variants of the most active catalyst indicate that a rigid backbone in the bidentate structure, strong electron donation, and severe hindrance all contribute to its high reactivity. Thus, these complexes constitute a fourth-generation catalyst for the amination of aryl halides, whose activity complements catalysts based on monophosphines and carbenes.

Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles

Resisting pathways for decomposition followed by palladium complexes of monodentate ligands is one characteristic of the highly reactive but long-lived catalyst generated from the Josiphos ligand L and palladium. It catalyzes under mild conditions the coupling of primary amines with chloropyridines and chloroarenes in high yield with low catalyst loadings (see scheme).

Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation

The initial finding that the p-methylaminophenol (6) exhibited antioxidant activity led us to investigate whether the length of alkyl chains linked to the aminophenol residue might affect antioxidative activity. Therefore, we synthesized p-butylaminophenol (5), p-hexylaminophenol (4), p-octylaminophenol (3), and p-methoxybenzylaminophenol (7). All p-alkylaminophenols quenched α,α-diphenyl-β-picrylhydrazyl (DPPH) radicals, with 7 being the most potent DPPH radical scavenger. Lipid peroxidation by rat liver microsomes was reduced by p-alkylaminophenols in dose- and aminophenol alkyl chain length-dependent fashion (3>4>5>6), with 3 being the most potent lipid peroxidation inhibitor, at approximately 350-fold higher potency than 6. These results indicate that elongation of alkyl chains in p-alkylaminophenols may increase antioxidative activity, and that p-alkylaminophenols may potentially be useful in the development of antioxidants.

Process for the manufacture of fluoran compounds

A process for the preparation of a fluoran compound of the formula STR1 wherein R, R1, R2 and R4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy, R3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX3 X4, or (R1 and R2) or (R3 and R4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus, X1, X2, X3 and X4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X1 and X2) or (X3 and X4) are each independently together with the nitrogen to which are attached a 5- or 6-membered heterocyclic ring, and the ring A is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkylthio, lower alkoxy, lower alkoxycarbonyl, amino, mono-lower alkylamino, di-lower alkylamino or lower alkyl carbonylamino, which process comprises (1) reacting a ketonic acid of the formula STR2 with a substituted phenol derivative of the formula STR3 wherein Z is hydrogen, lower alkyl, formyl or lower alkanoyl and A, R, R1, R2, R3, R4, X1 and X2 have the given meanings, (2) adding the reaction product to an aqueous-organic liquor containing a non-polar organic solvent and a base at a temperature of 50° to 90° C., (3) separating the organic phase and (4) removing the organic solvent to obtain the fluoran of the formula (1).

ONE-POT CHEMOSELECTIVE REDUCTIVE ALKYLATION OF NITROARENES: A NEW GENERAL METHOD OF SYNTHESIS OF ALKYLANILINES.

A New facile and general synthesis of alkylanilines by one-pot reductive alkylation of nitroarenes is reported.This method is based on the "in situ" reduction by hydrides (LiAlH4 or NaBH4) in the presence of catalytic amounts of Pd/C, of nitronate adducts arising from the conjugate addition of Grignard reagents to mononitroarenes.LiAlH4 showed to be a more efficient but less selective reducing agent than NaBH4.The reaction can be successfully applied to mono, homo and hetero bicyclic systems and allows to introduce a large variety of alkyl chains without isomerisation phenomena.