22424-58-4

Basic information

• Product Name: 5-BENZYLOXY-2-NITROTOLUENE
• Synonyms: 4-BENZYLOXY-2-METHYL-1-NITRO-BENZENE;5-BENZYLOXY-2-NITROTOLUENE;Benzene, 2-methyl-1-nitro-4-(phenylmethoxy)-;2-BENZYLOXY-2-NITROTOLUENE;5-BENZOXY-2-NITROTOLUENE;(3-Methyl-4-nitrophenyl)benzyl ether;2-Methyl-1-nitro-4-(phenylmethoxy)benzene;Benzyl 4-Nitro-m-tolyl ether
• CAS NO: 22424-58-4
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.26
• EINECS: 244-988-3
• Mol File: 22424-58-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 69-70°C
• Boiling Point: 400.3 °C at 760 mmHg
• Flash Point: 176.8 °C
• Appearance: /
• Density: 1.202 g/cm³
• Vapor Pressure: 3.37E-06mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 1978227
• CAS DataBase Reference: 5-BENZYLOXY-2-NITROTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZYLOXY-2-NITROTOLUENE(22424-58-4)
• EPA Substance Registry System: 5-BENZYLOXY-2-NITROTOLUENE(22424-58-4)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 22424-58-4(Hazardous Substances Data)

Usage

General Description

5-Benzyloxy-2-nitrotoluene is a chemical compound that belongs to the class of organic compounds. These compounds, also known as aromatic benzenoids, are characterized by their benzene-based structures. 5-Benzyloxy-2-nitrotoluene is particularly utilized in the field of organic synthesis. It has a relatively complex molecular structure that includes a benzene ring substituted by a benzyloxy group at one position and a nitro group at another, as well as an additional methyl group. This chemical compound is generally designed for laboratory use only, and not for food, drug, or household use due to its highly reactive nature and potential health risks if improperly handled.

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

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

Downstream Products

• 153805-85-7 1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine 
• 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 
• 138335-03-2 (3S,4S)-7-Benzyloxy-3-hydroxy-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 

Relevant articles and documents

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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

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.