5-Benzyloxyindole

Base Information

• Chemical Name: 5-Benzyloxyindole
• CAS No.: 1215-59-4
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Hs Code.: 2933.99 DERIVATION
• European Community (EC) Number: 214-930-1
• NSC Number: 62895
• UNII: YCI4Z02E1C
• DSSTox Substance ID: DTXSID80153285
• Nikkaji Number: J40.604J
• Wikidata: Q27294452
• ChEMBL ID: CHEMBL1288719
• Mol file: 1215-59-4.mol

Synonyms:5-Benzyloxyindole;1215-59-4;5-(Benzyloxy)-1H-indole;1H-Indole, 5-(phenylmethoxy)-;5-Benzyloxy-1H-indole;Benzyloxy-5 indole;INDOLE, 5-BENZYLOXY-;Indole, 5-(benzyloxy)-;5-phenylmethoxy-1H-indole;5-(Benzyloxy)indole;MFCD00005676;5-(phenylmethoxy)indole;5-benzoxyindole;NSC 62895;Benzyloxy-5 indole [French];EINECS 214-930-1;UNII-YCI4Z02E1C;BRN 0173532;YCI4Z02E1C;5-(Phenylmethoxy)-1H-indole;NSC-62895;5-21-03-00019 (Beilstein Handbook Reference);5-benzyloxy-indol;5-benzyloxy indole;5-benzyloxy-indole;5-phenylmethoxyindole;Maybridge3_006788;Oprea1_825327;5-(Benzyloxy)indole, 95%;BIDD:GT0311;SCHEMBL329575;5-(Benzyloxy)-1H-indole #;WLN: T56 BMJ GO1R;CHEMBL1288719;DTXSID80153285;5-[(phenylmethyl)oxy]-1H-indole;HMS1450E12;BCP26888;NSC62895;STR00813;BENZYL 1H-INDOL-5-YL ETHER;BBL010818;STK801770;AKOS000506156;AB00490;CCG-247307;CG-0512;CS-W013088;IDI1_018175;2- Nitro-2`,4`-dichloro-diphenylether;NCGC00324807-01;AC-27781;LS-82367;SY004490;AM20060941;B1833;FT-0602806;B-1620;AB01320182-02;Q27294452;F0001-2641

Chemical Property of 5-Benzyloxyindole

Chemical Property:

• Appearance/Colour: Off-white to beige powder
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Melting Point: 100-104 °C(lit.)
• Refractive Index: 1.669
• Boiling Point: 411.6 °C at 760 mmHg
• PKA: 16.63±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.: ethanol: may be hazy yellow
• XLogP3: 3.6
• 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

5-Benzyloxyindole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)NC=C3
• Uses: 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. 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 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.

Technology Process of 5-Benzyloxyindole

There total 24 articles about 5-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: 99.0%

5-benzyloxyindole-3-carboxylic acid (24370-73-8) → 5-benzyloxy-1H-indole (1215-59-4)

Guidance literature:

In acetonitrile; at 140 ℃; Schlenk technique;

DOI:10.1080/00397911.2019.1703137

Reference yield: 95.0%

1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine (153805-85-7) → 5-benzyloxy-1H-indole (1215-59-4)

Guidance literature:

With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate; In isopropyl alcohol; at 80 ℃; for 5h;

DOI:10.1007/s10593-011-0776-2

Reference yield: 91.0%

indol-5-ol (1953-54-4) + benzyl bromide (100-39-0) → 5-benzyloxy-1H-indole (1215-59-4)

Guidance literature:

With 18-crown-6 ether; caesium carbonate; In acetone; at 20 ℃;

upstream raw materials:

5-benzyloxy-1H-indole-2-carboxylic acid

5-Benzyloxy-2,ω-dinitro-styrol

2-Amino-5-(benzyloxy)-α-chloracetophenon

5-benzyloxy-2-nitrotoluene

Downstream raw materials:

5-benzyloxy-3-(3-carbmethoxybenzoyl)indole

2,5-dihydro-3-[6-benzyloxy-1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-4-(5-benzyloxy-1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione

5-(phenylmethoxy)-1H-indole-3-acetic acid ethyl ester

3-[5-(benzyloxy)indole-3-yl]-4-methoxy-2-nitrobutanoic acid ethyl ester

Refernces

• 1、 Abe, Takumi,Haruyama, Tomohiro,Yamada, Koji. "C4 Pictet-Spengler Reactions for the Synthesis of Core Structures in Hyrtiazepine Alkaloids". . p. 4141 - 4150. Retrieved 2017.
• 2、 Chen, Xia,Zhou, Xiao-Yu. "Decarboxylation of indole-3-carboxylic acids under metal-free conditions". supporting information. p. 805 - 812. Retrieved 2020/02/20.
• 3、 -. "LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF". Paragraph 00365. . Retrieved 2017/01/23.