7-Benzyloxyindole

Base Information

• Chemical Name: 7-Benzyloxyindole
• CAS No.: 20289-27-4
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Hs Code.: 29339990
• European Community (EC) Number: 678-203-4
• NSC Number: 92526
• DSSTox Substance ID: DTXSID90942425
• Nikkaji Number: J586.352J
• Wikidata: Q72442307
• Mol file: 20289-27-4.mol

Synonyms:7-Benzyloxyindole;20289-27-4;7-(Benzyloxy)-1H-indole;7-(phenylmethoxy)indole;7-phenylmethoxy-1H-indole;1H-INDOLE, 7-(PHENYLMETHOXY)-;MFCD00037974;7-Benzyloxy-1H-indole;7-Benzyloxindole;7-benzyloxy indole;NSC92526;7-(Benzyloxy)indole;7-Benzyloxyindole, 96%;7-(phenylmethoxy)-1H-indole;SCHEMBL837602;7-(Benzyloxy)-1H-indole #;DIGZMTAFOACVBW-UHFFFAOYSA-;DTXSID90942425;Isobutyl2,4-dichlorophenoxyacetate;NSC-92526;AKOS005254286;AB01684;AC-5096;CS-W007899;DS-0068;SY018015;AM20050293;B2846;FT-0601243;B-1660;EN300-174996;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

Chemical Property of 7-Benzyloxyindole

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Melting Point: 70-74 °C
• Refractive Index: 1.669
• Boiling Point: 411.6 °C at 760 mmHg
• PKA: 16.36±0.30(Predicted)
• Flash Point: 148.9 °C
• PSA: 25.02000
• Density: 1.196 g/cm³
• LogP: 3.74690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• 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:

98%,99%, ^*data from raw suppliers

7-Benzyloxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC=CC3=C2NC=C3
• Uses: Indole analogue as inhibitor 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

Technology Process of 7-Benzyloxyindole

There total 23 articles about 7-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: 90.0%

7-Indolol (2380-84-9) + benzyl bromide (100-39-0) → 7-benzyloxyindole (20289-27-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201904987

Reference yield: 76.0%

3-benzyloxy-2-nitrophenylacetaldehyde semicarbazone → 7-benzyloxyindole (20289-27-4)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; for 1h; Heating;

DOI:10.1081/SCC-120015783

Reference yield: 71.0%

C21H16ClNO4S → 7-benzyloxyindole (20289-27-4)

Guidance literature:

With sodium tetrahydroborate; tert-butyl alcohol; In tetrahydrofuran; at 50 ℃;

DOI:10.1021/acs.orglett.9b01690

upstream raw materials:

2-benzyloxynitrobenzene

vinyl magnesium bromide

(E)-3-benzyloxy-2-nitro-β-pyrrolidinostyrene

3-methyl-2-nitrophenol

Downstream raw materials:

3,4-bis-(7-benzyloxy-1H-indol-3-yl)-1-methyl-pyrrole-2,5-dione

C₄₀H₃₅N₃O₆

N-acetyl-DL-tryptophan

7-benzyloxy-1-methyl-1H-indole

Refernces

• 1、 Harada, Hiroshi,Fujii, Akihito,Kato, Shiro. "An efficient and practical synthesis of N,N-diethyl-7-indolyloxyacetamide via 7-hydroxyindole". . p. 507 - 514. Retrieved 2003.
• 2、 Ueda, Hirofumi,Satoh, Hitoshi,Sugimoto, Kenji,Tokuyama, Hidetoshi,Matsumoto, Koji,Fukuyama, Tohru. "Total synthesis of (+)-haplophytine". supporting information; experimental part. p. 7600 - 7603. Retrieved 2009/12/28.