6-Benzyloxyindole

Base Information

• Chemical Name: 6-Benzyloxyindole
• CAS No.: 15903-94-3
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Hs Code.: 29339990
• European Community (EC) Number: 810-565-2
• NSC Number: 92538
• DSSTox Substance ID: DTXSID00293834
• Nikkaji Number: J1.037.401D
• Wikidata: Q72442300
• Mol file: 15903-94-3.mol

Synonyms:6-Benzyloxyindole;15903-94-3;6-(Benzyloxy)-1H-indole;6-phenylmethoxy-1H-indole;MFCD00053554;6-(Benzyloxy)indole;6-benzyloxy-1H-indole;1H-INDOLE, 6-(PHENYLMETHOXY)-;6-benzoxyindole;6-benzyloxy indole;6-Benzyloxy-indole;NSC92538;6-Phenylmethoxyindole;6-(Benzyloxy)-1H-indol;SCHEMBL707702;6-(Benzyloxy)-1H-indole #;6-Benzyloxyindole, crystalline;DTXSID00293834;BBL010838;NSC 92538;NSC-92538;STK634037;AKOS005206924;AB02240;CS-W007642;PS-7798;NCGC00342384-01;AC-27775;SY025663;AM20060947;B2809;FT-0601224;B-1640;EN300-136589;AB01334040-02;A809996;J-650074;Z1676355557

Chemical Property of 6-Benzyloxyindole

Chemical Property:

• Appearance/Colour: Colourless crystalline solid
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Melting Point: 116 - 119 °C
• Refractive Index: 1.669
• Boiling Point: 411.6 °C at 760 mmHg
• PKA: 17.17±0.30(Predicted)
• Flash Point: 148.9 °C
• PSA: 25.02000
• Density: 1.196 g/cm³
• LogP: 3.74690
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Diethyl Ether (Slightly), Ethanol (Slightly), Ethyl Aceta
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 223.099714038
• Heavy Atom Count: 17
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

6-Benzyloxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)C=CN3
• Uses: Indole derivative, as antiviral and antitumor agent Reactant for enantioselective synthesis of quaternary carbon-containing 3-(3-indolyl)isoindolin-1-onesReactant for Friedel-Crafts alkylation reactions with hydroxyisoindolinonesReactant for direct and regioselective synthesis of β-heteroarylated ketonesReactant for preparation of hepatitis C virus (HCV) inhibitorsReactant for preparation of protein kinase C (PKC) inhibitorsReactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands

Technology Process of 6-Benzyloxyindole

There total 18 articles about 6-Benzyloxyindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-Benzyloxy-6-(2-pyrrolidinylvinyl)nitrobenzene (153805-86-8) → 6-benzyloxy-1H-indole (15903-94-3)

Guidance literature:

With hydrogen; 5% rhodium-on-charcoal; iron(II) sulfate; In tetrahydrofuran; at 22 - 25 ℃; for 16h;

Reference yield: 96.0%

3-Benzyloxy-6-(2-pyrrolidinylvinyl)nitrobenzene (153805-86-8) → 6-hydroxy-1H-indole (2380-86-1) + 6-benzyloxy-1H-indole (15903-94-3)

Guidance literature:

With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate; In tetrahydrofuran; at 20 ℃; for 9h;

Reference yield: 82.0%

6-(benzyloxy)-1H-indole-2-carboxylic acid (40047-22-1) → 6-benzyloxy-1H-indole (15903-94-3)

Guidance literature:

With quinoline; copper; Heating;

DOI:10.1016/j.bmcl.2006.06.093

upstream raw materials:

6-(benzyloxy)-1H-indole-2-carboxylic acid

2-Amino-4-(benzyloxy)-α-chloracetophenon

(E)-5-(benzyloxy)-2-<2-(dimethylamino)vinyl>nitrobenzene

3-Benzyloxy-6-(2-pyrrolidinylvinyl)nitrobenzene

Downstream raw materials:

(6-benzyloxy-indol-3-yl)-oxoacetyl chloride

3-(dimethylaminomethyl)-6-benzyloxyindole

6-benzyloxy-1H-indole-3-carboxaldehyde

6-Benzyloxy-3-(2-pyridin-4-yl-ethyl)-1H-indole

Refernces

• 1、 Akao, Atsushi,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi. "Development of large-scale preparations of indole derivatives: Evaluation of potential thermal hazards and studies of reaction kinetics and mechanisms". . p. 1178 - 1183. Retrieved 2006.
• 2、 Gim, Hyo Jin,Li, Hua,Jeong, Ji Hye,Lee, Su Jeong,Sung, Mi-Kyung,Song, Mi-Young,Park, Byung-Hyun,Oh, Soo Jin,Ryu, Jae-Ha,Jeon, Raok. "Design, synthesis, and biological evaluation of a series of alkoxy-3-indolylacetic acids as peroxisome proliferator-activated receptor γ/δ agonists We dedicate this article to Professor Young-Ger Suh on the occasion of his retirement.". supporting information. p. 3322 - 3336. Retrieved 2015/08/03.