22424-58-4

Usage

Uses

Used in Organic Synthesis:
5-Benzyloxy-2-nitrotoluene is used as an intermediate in the synthesis of various organic compounds. Its complex molecular structure allows for the creation of a wide range of chemical products, making it a valuable component in the field of organic chemistry.
Used in Research and Development:
Due to its unique properties, 5-Benzyloxy-2-nitrotoluene is employed in research and development settings to study the behavior of aromatic benzenoids and their potential applications in various industries. This includes exploring its reactivity, stability, and interactions with other compounds.
Used in Laboratory Applications:
5-Benzyloxy-2-nitrotoluene is used as a reagent in laboratory experiments, where its highly reactive nature can be controlled and monitored. It is essential for conducting research on the synthesis and properties of related organic compounds, as well as for educational purposes in teaching the principles of organic chemistry.

InChI:InChI=1/C14H13NO3/c1-11-9-13(7-8-14(11)15(16)17)18-10-12-5-3-2-4-6-12/h2-9H,10H2,1H3

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 22424-59-5 (5-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 2581-34-2 3-methyl-4-nitrophenol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 22424-59-5 (5-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 138334-86-8 2-[2-(5-Benzyloxy-2-nitro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester 
• 1215-59-4 5-benzyloxy-1H-indole 
• 153805-85-7 1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine 
• 4792-60-3 2-methyl-4-benzyloxyaniline 
• 32991-04-1 trans-5-benzyloxy-β-(dimethylamino)-2-nitrostyrene 
• 705961-42-8 (5-benzyloxy-2-nitrophenyl)-acetaldehyde 
• 55581-41-4 5-benzyloxy-1H-indole-2-carboxylic acid methyl ester 
• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 21598-06-1 5-hydroxyindole-2-carboxylic acid 
• 1953-54-4 indol-5-ol 
• 24370-81-8 ethyl 5-benzyloxy-1H-indole-1-carboxylate 
• 138334-56-2 Acetic acid (3S,4R)-7-benzyloxy-1-(2-dimethylamino-ethyl)-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester 
• 138335-03-2 (3R,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING CFTR

The present disclosure is directed to disclosed compounds that modulate, e.g., address underlying defects in cellular processing of CFTR activity.

Synthesis of a deuterium-labelled standard of bufotenine (5-HO-DMT)

The Batcho-Leimgruber strategy was employed to synthesize 3-(2-dimethylamino-[2H4]-ethyl)-1H-indol-5-ol (bufotenine, 5-HO-DMT) (8) from commercial 3-methyl-4-nitro-phenol (1), benzyl bromide and N,N-dimethylformamide-dimethylacetal. Compound 4 was synthesized from compound 3 using the Batcho-Leimgruber strategy in the presence of Raney nickel and hydrazine hydrate. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum [2H4]-hydride to yield [2-(5-benzyloxy-1H-indol-3-yl)-[2H4]-ethyl] -dimethyl-amine (7). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8. Copyright

A novel phase-switching protecting group for multi-step parallel solution phase synthesis

A new phase-tag 1 which facilitates the parallel solution phase synthesis of carboxylic acids, esters, and carboxamides is reported. The new phase tag assists compound purification by enabling the selective resin capture of reaction products in either a reversible pH dependent manner (solid-phase extraction), or irreversibly in a Diels-Alder reaction.

Novel 6-substituted uracil analogs as inhibitors of the angiogenic actions of thymidine phosphorylase

Thymidine phosphorylase (TP) catalyzes the reversible phosphorolysis of thymidine and other pyrimidine 2′-deoxyribonucleosides. In addition, TP has been shown to possess angiogenic activity in a number of in vitro and in vivo assays, and its angiogenic activity has been linked to its catalytic activity. A series of 5- and 6-substituted uracil derivatives were synthesized and evaluated for their abilities to inhibit TP activity. Among the most active compounds was a 6-amino-substituted uracil analog, 6-(2-aminoethyl)amino-5-chlorouracil (AEAC), which was a competitive inhibitor with a Ki of 165 nM. The inhibitory activity of AEAC was selective for TP, as it did not inhibit purine nucleoside phosphorylase or uridine phosphorylase at concentrations up to 1 mM. Human recombinant TP induced human umbilical vein endothelial cell (HUVEC) migration in a modified Boyden chamber assay in vitro, and this action could be abrogated by the TP inhibitors. The actions of the inhibitors were specific for TP, as they had no effect on the chemotactic actions of vascular endothelial growth factor (VEGF). HUVEC migration was also induced when TP-transfected human colon and breast carcinoma cells were co-cultured in the Boyden chamber assay in place of the purified angiogenic factors, and a TP inhibitor blocked the tumor cell-mediated migration almost completely. These studies suggest that inhibitors of TP may be useful in pathological conditions that are dependent upon TP-driven angiogenesis.

A novel safety-catch linker for the solid-phase synthesis of amides and esters

(matrix presented) A new safety-catch linker for solid-phase organic synthesis is described. Synthesis and attachment of the linker to the solid phase was achieved via a simple and high-yielding strategy. The linker was exemplified by acylation to form unactivated amides, activation of the linker, and cleavage to release acyl moieties. Acids, amides, or esters were released under mild conditions and with exceptionally high purity. The reactivities of unactivated and activated amides are compared.

5-HT4 receptor agonists

Compounds of formula (I) and pharmaceutically acceptable salts thereof are selective agonists for 5-HT4 receptors. STR1 wherein Ak is a C3 -C6 alkyl group, and R is a C2 -C6 alkyl group, a C3 -C6 alkenyl group, a C3 -C6 alkynyl group, a C3 -C7 cycloalkyl group or a C3 -C6 cycloalkylmethyl group.

Practical synthesis of indolopyrrolocarbazoles

A practical method for the synthesis of an indolo[2,3-a]pyrrolo[3,4- c]carbazole ring system is described. The method involves two key processes: a coupling reaction between indole and substituted methylmaleimide portions using lithium hexamethyldisilazide (LiHMDS) as a base, and the oxidative cyclization of bisindolylmaleimide with palladium (II) chloride. We applied this method to the synthesis of arcyriaflavin B (5), C (6) and D (7).

The serotonin 5-HT4 receptor. 2. Structure-activity studies of the indole carbazimidamide class of agonists.

A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonist described so far (EC50 = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, Ki = 12 nM) to and 300-fold higher (1h, Ki = 0.04 nM) than serotonin.

The synthesis of 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole . A potential antidepressant agent

The structures of doxepin and serotonin were overlayed using molecular graphics and 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole was proposed as a potential antidepressant agent. This paper deals with the synthesis of the title compound. Key steps in the synthesis include a regioselective electrophilic substitution at C-4 of ethyl 5-hydroxy-1-indolecarboxylate and subsequent modification to 7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole. Standard procedures were then used to construct the dimethylaminoethyl side chain to yield the title compound.

Intermediates for indoles

Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.