5-Benzyloxyindole-3-carboxaldehyde

Base Information

• Chemical Name: 5-Benzyloxyindole-3-carboxaldehyde
• CAS No.: 6953-22-6
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• Hs Code.: 29339990
• European Community (EC) Number: 230-134-7
• NSC Number: 71049
• DSSTox Substance ID: DTXSID90219785
• Nikkaji Number: J265.993J
• Wikidata: Q72442326
• ChEMBL ID: CHEMBL1592937
• Mol file: 6953-22-6.mol

Synonyms:6953-22-6;5-Benzyloxyindole-3-carboxaldehyde;5-Benzyloxyindole-3-carbaldehyde;5-(Benzyloxy)-1H-indole-3-carbaldehyde;5-benzyloxy-3-formylindole;5-benzyloxy-1h-indole-3-carbaldehyde;5-(Phenylmethoxy)-1H-indole-3-carbaldehyde;1H-Indole-3-carboxaldehyde, 5-(phenylmethoxy)-;MFCD00014562;5-phenylmethoxy-1H-indole-3-carbaldehyde;5-Benzyloxy-indole-3-carboxaldehyde;EINECS 230-134-7;5-Benzyloxy-3-indolecarboxaldehyde;5-(Benzyloxy)indole-3-carbaldehyde;NSC71049;5-Benzyloxyindol-3-aldehyde;MLS001360008;SCHEMBL1791105;CHEMBL1592937;DTXSID90219785;HMS3052E22;5-Benzyloxyindole-3- carboxaldehyde;5-benzyloxy indole-3-carboxyaldehyde;BBL027808;NSC 71049;NSC-71049;STK935208;AKOS005207077;AB01159;CS-W014096;DS-0066;PS-7463;NCGC00247293-01;AC-18163;AC-24616;SMR001224347;SY026618;5-Benzyloxyindole-3-carboxaldehyde, powder;5-(Benzyloxy)-1H-indole-3-carbaldehyde #;A9195;AM20060948;FT-0620054;B-1870;EN300-206737;5-(benzyloxy)-1H-indole-3-carbaldehyde

Chemical Property of 5-Benzyloxyindole-3-carboxaldehyde

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 237-238 °C
• Boiling Point: 474.2 °C at 760 mmHg
• PKA: 15.13±0.30(Predicted)
• Flash Point: 240.6 °C
• PSA: 42.09000
• Density: 1.267 g/cm³
• LogP: 3.55940
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Ethanol
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

5-Benzyloxyindole-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)NC=C3C=O
• Uses: Reactant for preparation of:Rhodanine merocyanine dyesPotential topoisomerase II inhibitorsAzithromycin derivativesInhibitors of PI3 kinase-α and the mammalian target of rapamycinCytotoxic agentsVascular endothelial growth factor (VEGF) inhibitorDerivatives of vancomycin and eremomycinBenzimidazoles as potential antibacterial agentsLight-dependent tumor necrosis factor-α antagonistsSerotonin 5-HT4 Receptor agonists An antibacterial agent

Technology Process of 5-Benzyloxyindole-3-carboxaldehyde

There total 14 articles about 5-Benzyloxyindole-3-carboxaldehyde 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: 91.0%

1H-imidazole (288-32-4) + 5-benzyloxy-1H-indole (1215-59-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Guidance literature:

1H-imidazole; 5-benzyloxy-1H-indole; With acetic anhydride; at 130 ℃; for 1h;

With sodium hydroxide; In ethanol; water; for 1h; Further stages.; Heating;

DOI:10.1248/cpb.55.922

Reference yield: 84.0%

5-benzyloxy-1H-indole (1215-59-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; for 0.25h;

5-benzyloxy-1H-indole; at 50 - 60 ℃; for 1.5h;

With sodium hydroxide; In water; at 0 ℃; for 0.0333333h; Heating / reflux;

Reference yield: 80.0%

→ 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Guidance literature:

With trichlorophosphate; at 10 - 35 ℃; for 0.75h; Inert atmosphere;

upstream raw materials:

5-benzyloxy-1H-indole

N,N-dimethyl-formamide

trichlorophosphate

1H-imidazole

Downstream raw materials:

5-benzyloxy-3-(2-nitro-cis-propenyl)-indole

5-benzyloxy-3-(2-nitro-vinyl)-indole

5-benzyloxy-3-(2-nitro-non-1-enyl)-indole

5-benzyloxy-3-(2-nitro-but-1-enyl)-indole

Refernces

• 1、 -. "NOVEL COMPOUNDS AND THEIR USES AS THYROID HORMONE RECEPTOR AGONISTS". Page/Page column 58. . Retrieved 2020/09/08.
• 2、 Abe, Takumi,Haruyama, Tomohiro,Yamada, Koji. "C4 Pictet-Spengler Reactions for the Synthesis of Core Structures in Hyrtiazepine Alkaloids". . p. 4141 - 4150. Retrieved 2017/09/13.