20289-27-4

Basic information

• Product Name: 7-Benzyloxyindole
• Synonyms: 7-benzyloxyindolecrystalline;7-(Phenylmethoxy)-1H-indole;NSC 92526;7-Benzyloxyindole 98%;7-BENZYLOXYINDOLE 98+%;1H-Indole,7-(phenylMethoxy)-;7-(PHENYLMETHOXY)INDOLE;7-BENZYLOXYINDOLE
• CAS NO: 20289-27-4
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.27
• Product Categories: blocks;IndolesOxindoles;Indoles and derivatives;Indoline & Oxindole;Indole Series;Indoles;Simple Indoles;Indole;Aromatics;Indole Derivatives;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 20289-27-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 70-74 °C
• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 148.9 °C
• Appearance: Off-white crystalline powder
• Density: 1.196 g/cm³
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 16.36±0.30(Predicted)
• CAS DataBase Reference: 7-Benzyloxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Benzyloxyindole(20289-27-4)
• EPA Substance Registry System: 7-Benzyloxyindole(20289-27-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 20289-27-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale-Yellow Solid

Uses

Different sources of media describe the Uses of 20289-27-4 differently. You can refer to the following data:
1. Indole analogue as inhibitor
2. Reactant for preparation of pyrazolo-quinoline derivatives as adenosine receptor antagonistsReactant for asymmetric total synthesis of diazonamide AReactant for preparation of HCV inhibitorReactant for preparation of substituted 3-cyanoindoles and 3-(4-pyridinyl)indoles as inhibitors of inosine monophosphate dehydrogenase, with antiproliferative activity on peripheral blood mononuclear cells (PMBC)Reactant for preparation of [(indolyl)methyl]hydantoin and -thiohydantoin derivatives as treatment of necroptosisReactant for preparation of regioisomeric analogs of ED-110, indolocarbazole poisons of human topoisomerase I

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

Upstream product

• 4560-41-2 2-benzyloxynitrobenzene 
• 1826-67-1 vinyl magnesium bromide 
• 876862-89-4 (E)-3-benzyloxy-2-nitro-β-pyrrolidinostyrene 
• 61535-21-5 1-(benzyloxy)-3-methyl-2-nitrobenzene 
• 100-39-0 benzyl bromide 
• 140640-07-9 7-(2-Cyano-1-methyl ethenyl) indole 
• 104019-20-7 1-(1H-indol-7-yl)ethan-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 169615-68-3 5-(benzyloxy)bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one 
• 2380-84-9 7-Indolol 
• 88-75-5 2-hydroxynitrobenzene 
• 4920-77-8 3-methyl-2-nitrophenol 

Downstream Products

• 94067-27-3 7-benzyloxygramine 
• 94254-23-6 (7-benzyloxy-indol-3-yl)-glyoxylic acid dimethylamide 
• 2380-84-9 7-Indolol 
• 220873-37-0 3-(7-benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-bromo-pyrrole-2,5-dione 
• 220873-43-8 3-(7-Benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-[7-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 92855-65-7 7-(benzyloxy)-1H-indole-3-carbaldehyde 
• 475577-34-5 7-benzyloxy-1-methyl-1H-indole 
• 941575-98-0 C₂₀H₁₉NO₄ 
• 941575-87-7 3-(benzofuran-3-yl)-4-(7-benzyloxy-1-methyl-1H-indol-3-yl)pyrrole-2,5-dione 
• 220873-40-5 1-Benzyloxymethyl-3-[7-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-4-bromo-pyrrole-2,5-dione 
• 122142-30-7 C₁₇H₁₂ClNO₃ 
• 1000786-72-0 C₁₇H₁₇NO₂ 
• 191730-78-6 7-benzyloxyindoline 
• 24370-75-0 7-benzyloxy-indole-3-carboxylic acid 

Relevant articles and documents

Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate

An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles

Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.