1215-59-4

Basic information

• Product Name: 5-Benzyloxyindole
• Synonyms: 5-(Phenylmethoxy)-1H-indole;5-benzyloxy-indol;Benzyloxy-5 indole;Indole, 5-(benzyloxy)-;TIMTEC-BB SBB003331;BENZYLOXYINDOLE(5-);5-BENZYLOXY-1H-INDOLE;5-BENZYLOXYINDOLE
• CAS NO: 1215-59-4
• Molecular Formula: C15H13NO
• Molecular Weight: 223.27
• EINECS: 214-930-1
• Product Categories: blocks;IndolesOxindoles;Indoles and derivatives;Pyrroles & Indoles;Indoline & Oxindole;Indole Series;Indoles;Simple Indoles;Indole;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Aromatics;Indole Derivatives;Heterocycle-Indole series
• Mol File: 1215-59-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 100-104 °C(lit.)
• Boiling Point: 364.56°C (rough estimate)
• Flash Point: 148.9 °C
• Appearance: white to light yellow/powder
• Density: 1.0707 (rough estimate)
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: may be hazy yellow
• PKA: 16.63±0.30(Predicted)
• BRN: 173532
• CAS DataBase Reference: 5-Benzyloxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzyloxyindole(1215-59-4)
• EPA Substance Registry System: 5-Benzyloxyindole(1215-59-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25-22
• WGK Germany: 3
• RTECS: NL4850000
• F: 8-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 1215-59-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to beige powder

Uses

Different sources of media describe the Uses of 1215-59-4 differently. You can refer to the following data:
1. Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions Reactant in metal-free Friedel-Crafts alkylation reactions Reactant in preparation of protein kinase (PKC) inhibitors Reactant in preparation of indole/quinoline carbothioic acid amide derivatives.
2. Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydesReactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditionsReactant in metal-free Friedel-Crafts alkylation reactionsReactant in preparation of protein kinase (PKC) inhibitorsReactant in preparation of indole/quinoline carbothioic acid amide derivatives
3. 5-Benzyloxyindole is used as reagent/reactant in regioselective preparation of CF3-β-tryptamine derivatives via base-free thermal ring-opening reaction of N-nosyl-2-CF3-aziridine with indoles.

Purification Methods

It is recrystallised from *C6H6/pet ether or pet ether. The picrate forms red crystals from *C6H6 and has m 142-143o. [Burton & Leong Chem Ind (London) 1035 1953, Ek & Witkop J Am Chem Soc 76 5579 1954, fluorescence: Bridges & Williams Biochem J 107 225 1968, Beilstein 27 III/IV 1758.]

InChI:InChI=1/C15H13NO/c1-2-4-12(5-3-1)11-17-14-6-7-15-13(10-14)8-9-16-15/h1-10,16H,11H2

Upstream product

• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 92438-11-4 5-Benzyloxy-2,ω-dinitro-styrol 
• 24370-73-8 5-benzyloxyindole-3-carboxylic acid 
• 681180-19-8 C₁₅H₁₂BrNO 
• 100-44-7 benzyl chloride 
• 6373-46-2 p-benzyloxyaniline 
• 2581-34-2 3-methyl-4-nitrophenol 
• 32991-04-1 trans-5-benzyloxy-β-(dimethylamino)-2-nitrostyrene 
• 153805-85-7 1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine 
• 75-07-0 acetaldehyde 
• 51145-58-5 [4-(benzyloxy)phenyl]hydrazine 
• 16382-24-4 1-benzyl-5-(benzyloxy)-1H-indole 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 22424-58-4 5-benzyloxy-2-nitrotoluene 

Downstream Products

• 93331-75-0 5-benzyloxy-3-(2-nitro-ethyl)-indole 
• 93315-84-5 1-(5-(benzyloxy)-1H-indol-3-yl)ethan-1-one 
• 102750-01-6 5-benzyloxy-3-(2-nitro-1-phenyl-propyl)-indole 
• 103644-04-8 [2-(5-benzyloxy-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 
• 112551-98-1 5-benzyloxy-3-(2-nitro-1-phenyl-ethyl)-indole 
• 1453-97-0 5-benzyloxygramine 
• 6953-22-6 5-benzyloxyindole-3-carboxaldehyde 
• 96677-28-0 5,5'-bis-benzyloxy-1H,1'H-3,3'-(1-methyl-ethane-1,1-diyl)-bis-indole 
• 1953-54-4 indol-5-ol 
• 1006-94-6 5-methoxylindole 
• 24370-73-8 5-benzyloxyindole-3-carboxylic acid 
• 2436-15-9 NSC 73391 
• 110247-54-6 2-(5-(benzyloxy)-1H-indol-1-yl)-N,N-dimethylethan-1-amine 
• 25194-81-4 5-benzyloxy-3-(2-pyridin-4-yl-ethyl)-indole 

Relevant articles and documents

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.

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

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HYDROXYINDALPINE DERIVATIVES AND THEIR MEDICAL USE

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