5-Benzyloxygramine

Base Information

• Chemical Name: 5-Benzyloxygramine
• CAS No.: 1453-97-0
• Molecular Formula: C18H20N2O
• Molecular Weight: 280.37
• Hs Code.: 2933990090
• European Community (EC) Number: 215-927-8
• NSC Number: 17819
• UNII: 6L6Y39XT2Z
• DSSTox Substance ID: DTXSID40162974
• Nikkaji Number: J129E
• Wikidata: Q83031798
• ChEMBL ID: CHEMBL4451818
• Mol file: 1453-97-0.mol

Synonyms:5-benzyloxy-gramine;5-benzyloxygramine

Chemical Property of 5-Benzyloxygramine

Chemical Property:

• Appearance/Colour: white to off-white fine crystalline powder
• Vapor Pressure: 5.06E-08mmHg at 25°C
• Melting Point: 137-139 °C(lit.)
• Boiling Point: 442.3 °C at 760 mmHg
• PKA: 16.63±0.30(Predicted)
• Flash Point: 221.3 °C
• PSA: 28.26000
• Density: 1.153g/cm³
• LogP: 3.80850
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 280.157563266
• Heavy Atom Count: 21
• Complexity: 314

Purity/Quality:

98%min ^*data from raw suppliers

5-Benzyloxygramine Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1=CNC2=C1C=C(C=C2)OCC3=CC=CC=C3

Technology Process of 5-Benzyloxygramine

There total 5 articles about 5-Benzyloxygramine 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: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-benzyloxy-1H-indole (1215-59-4) + dimethyl amine (124-40-3) → 5-benzyloxygramine (1453-97-0)

Guidance literature:

formaldehyd; 5-benzyloxy-1H-indole; dimethyl amine; With acetic acid; In tetrahydrofuran; 1,4-dioxane; water; at 0 - 20 ℃; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1002/anie.200904388

Reference yield:

5-Benzyloxy-2,ω-dinitro-styrol (92438-11-4) → 5-benzyloxygramine (1453-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol; acetic acid

2: acetic acid; dioxane

With 1,4-dioxane; ethanol; acetic acid;

DOI:10.1021/ja01651a001

Reference yield:

5-benzyloxy-1H-indole-2-carboxylic acid (6640-09-1) → 5-benzyloxygramine (1453-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: copper-powder; quinaldine / 245 - 250 °C

2: acetic acid; ethanol

With 2-methylquinoline; ethanol; copper; acetic acid;

DOI:10.1002/hlca.19550380619

upstream raw materials:

formaldehyd

5-benzyloxy-1H-indole

dimethyl amine

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

Downstream raw materials:

1,4-bis-(5-benzyloxy-indol-3-ylmethyl)-piperazine

N-acetyl-5-hydroxytryptamine

N‐{2‐[5‐(benzyloxy)‐1H‐indol‐3‐yl]ethyl}acetamide

(S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Refernces

• 1、 Pillaiyar, Thanigaimalai,Gorska, Ewelina,Schnakenburg, Gregor,Müller, Christa E.. "General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives". . p. 9902 - 9913. Retrieved 2018/08/01.
• 2、 Wood, Paul M.,Woo, L. W. Lawrence,Labrosse, Jean-Robert,Thomas, Mark P.,Mahon, Mary F.,Chander, Surinder K.,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.. "Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl} phenylsulfamate: Synthesis, SAR, crystal structure, and in vitro and in vivo activities". scheme or table. p. 1577 - 1593. Retrieved 2011/12/01.