5-Benzyloxyindole-3-acetic acid

Base Information

• Chemical Name: 5-Benzyloxyindole-3-acetic acid
• CAS No.: 4382-53-0
• Molecular Formula: C17H15NO3
• Molecular Weight: 281.311
• Hs Code.: 2933990090
• European Community (EC) Number: 624-470-7
• NSC Number: 68361
• DSSTox Substance ID: DTXSID80195943
• Nikkaji Number: J998.925K
• Wikidata: Q72442310
• ChEMBL ID: CHEMBL314108
• Mol file: 4382-53-0.mol

Synonyms:5-benzyloxyindole-3-acetic acid;BOIAA

Chemical Property of 5-Benzyloxyindole-3-acetic acid

Chemical Property:

• Vapor Pressure: 3.37E-12mmHg at 25°C
• Melting Point: 147-149 °C(Solv: ethanol, 50% (64-17-5))
• Refractive Index: 1.679
• Boiling Point: 533.199 °C at 760 mmHg
• PKA: 4.51±0.30(Predicted)
• Flash Point: 276.269 °C
• PSA: 62.32000
• Density: 1.314 g/cm³
• LogP: 3.37400
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 281.10519334
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

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

5-Benzyloxyindole-3-acetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)NC=C3CC(=O)O
• Uses: Reactant for preparation of:Inhibitors of Gli1-mediated transcription as potential anticancer agentsSynthetic analogs of spider toxins 5-Benzyloxyindole-3-acetic Acid can be used for biological study for molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid.

Technology Process of 5-Benzyloxyindole-3-acetic acid

There total 13 articles about 5-Benzyloxyindole-3-acetic acid 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:

sodium cyanide (773837-37-9) + 5-benzyloxygramine (1453-97-0) → 2-(5-benzyloxy-1H-indol-3-yl)acetic acid (4382-53-0)

Guidance literature:

sodium cyanide; 5-benzyloxygramine; In ethanol; water; at 26 - 100 ℃; for 60h;

With hydrogenchloride; water; pH=2;

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → 2-(5-benzyloxy-1H-indol-3-yl)acetic acid (4382-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 0.33 h / 0 °C

2: sat. aq. NaHCO₃ / diethyl ether / 0.5 h / Heating

3: methanol / 8 h / Heating

4: NaBH₄ / tetrahydrofuran / 10 h / Heating

With sodium tetrahydroborate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)76815-8

Reference yield:

NSC 73391 (2436-15-9) → 2-(5-benzyloxy-1H-indol-3-yl)acetic acid (4382-53-0)

Guidance literature:

With potassium hydroxide;

DOI:10.1002/hlca.19550380619

upstream raw materials:

4-(4-benzyloxy-phenylhydrazono)-butyric acid

NSC 73391

5-benzyloxygramine

5-benzyloxy-1H-indole

Downstream raw materials:

5-Hydroxyindole-3-acetic acid

5-benzyloxy-3-(2-hydroxyethyl)indole

4-Nitrophenyl <(5-Benzyloxy)-1H-indol-3-yl>acetate

methyl (5-benzyloxy-1H-indol-3-yl)acetate

Refernces

• 1、 Morales-Rios, Martha S.,Santos-Sanchez, Norma F.,Suarez-Castillo, Oscar R.,Joseph-Nathan, Pedro. "Aromatic bromination versus oxidation of indolylmalonates by bromine". . p. 305 - 311. Retrieved 2007/10/03.
• 2、 Guan, Xiangming,Borchardt, Ronald T.. "A convenient method for the synthesis of indole-3-acetic acids". . p. 3013 - 3016. Retrieved 2007/10/02.