Indole, 3-((dimethylamino)methyl)-5-nitro-

Base Information

• Chemical Name: Indole, 3-((dimethylamino)methyl)-5-nitro-
• CAS No.: 3414-64-0
• Molecular Formula: C₁₁H₁₃N₃O₂
• Molecular Weight: 219.243
• Hs Code.: 2933990090
• NSC Number: 56889
• DSSTox Substance ID: DTXSID10187730
• Nikkaji Number: J53.645H
• Wikidata: Q72494729
• ChEMBL ID: CHEMBL1881648
• Mol file: 3414-64-0.mol

Synonyms:5-Nitrogramine;3414-64-0;N,N-dimethyl-1-(5-nitro-1H-indol-3-yl)methanamine;INDOLE, 3-((DIMETHYLAMINO)METHYL)-5-NITRO-;N,N-dimethyl-5-nitro-1H-indole-3-methanamine;1H-Indole-3-methanamine, N,N-dimethyl-5-nitro-;MFCD00544197;NSC 56889;BRN 0216692;3-((Dimethylamino)methyl)-5-nitroindole;MLS002667850;Indole, 3-[(dimethylamino)methyl]-5-nitro-;3-(DIMETHYLAMINOMETHYL)-5-NITROINDOLE;4-22-00-04317 (Beilstein Handbook Reference);NSC56889;Oprea1_367827;CBDivE_000986;CBDivE_002690;SCHEMBL8538163;CHEMBL1881648;DTXSID10187730;SVNVKGIWGOHXPW-UHFFFAOYSA-N;HMS3089M21;AMY27516;NSC-56889;AKOS005259116;5-Nitro-3-dimethylaminomethyl-1H-indole;AC-27830;BS-25238;LS-82964;SMR001557607;SY248340;CS-0451345;FT-0667493;1H-Indole-3-methanamine,N-dimethyl-5-nitro-;dimethyl[(5-nitro-1H-indol-3-yl)methyl]amine;N-2795;A822097;SR-01000196476;SR-01000196476-1

Chemical Property of Indole, 3-((dimethylamino)methyl)-5-nitro-

Chemical Property:

• Vapor Pressure: 6.51E-06mmHg at 25°C
• Melting Point: 166-169°C
• Boiling Point: 377.9°Cat760mmHg
• Flash Point: 182.4°C
• PSA: 64.85000
• Density: 1.287g/cm³
• LogP: 2.66090
• Storage Temp.: -20°C Freezer
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 219.100776666
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

98%min ^*data from raw suppliers

N,N-Dimethyl-5-nitrotryptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1=CNC2=C1C=C(C=C2)[N+](=O)[O-]
• Uses: N,N-Dimethyl-5-nitrotryptamine (cas# 3414-64-0) is a compound useful in organic synthesis.

Technology Process of Indole, 3-((dimethylamino)methyl)-5-nitro-

There total 5 articles about Indole, 3-((dimethylamino)methyl)-5-nitro- 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: 73.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-nitroindole (6146-52-7) + dimethyl amine (124-40-3) → N,N-dimethyl-5-nitro-1H-indole-3-methanamine (3414-64-0)

Guidance literature:

formaldehyd; dimethyl amine; With acetic acid; at 0 ℃; for 0.5h;

5-nitroindole; at 20 ℃; for 72h;

With sodium hydroxide; In water; at 0 ℃; pH=13;

DOI:10.1039/c7ob02529g

Reference yield:

eschenmoser's salt (33797-51-2) + 5-nitroindole (6146-52-7) → N,N-dimethyl-5-nitro-1H-indole-3-methanamine (3414-64-0) + C11H13N3O2

Guidance literature:

In acetonitrile; at 20 ℃; Overall yield = 53 %;

DOI:10.1055/s-0034-1378925

Reference yield:

5-nitro-1H-indole-3-carbaldehyde (6625-96-3) + dimethyl amine (124-40-3) → N,N-dimethyl-5-nitro-1H-indole-3-methanamine (3414-64-0)

Guidance literature:

5-nitro-1H-indole-3-carbaldehyde; dimethyl amine; In ethanol; acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

With sodium tetrahydroborate; In ethanol; acetonitrile; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/cmdc.202000835

upstream raw materials:

formaldehyd

5-nitroindole

dimethyl amine

eschenmoser's salt

Downstream raw materials:

5-nitro-1H-indole-3-carbaldehyde

<5-Nitro-indolyl-(3)>-acetonitril

N,N-dimethyl-1-(5-amino-1H-indol-3-yl)methanamine

5-nitro-DL-tryptophan

Refernces

• 1、 Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald. "Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity". . p. 1667 - 1679. Retrieved 2021/03/24.
• 2、 Grugel, Christian P.,Breit, Bernhard. "Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines". supporting information. p. 9672 - 9676. Retrieved 2019/12/24.