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

Base Information

• Chemical Name: N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine
• CAS No.: 30218-58-7
• Molecular Formula: C12H16 N2
• Molecular Weight: 188.272
• Hs Code.: 2933990090
• NSC Number: 88884
• UNII: 1UL0HR1QXC
• DSSTox Substance ID: DTXSID10184320
• Nikkaji Number: J36.995K
• Wikidata: Q72491078
• ChEMBL ID: CHEMBL4584108
• Mol file: 30218-58-7.mol

Synonyms:30218-58-7;5-Methylgramine;N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine;1H-Indole-3-methanamine, N,N,5-trimethyl-;INDOLE, 3-(DIMETHYLAMINO)METHYL-5-METHYL-;NSC 88884;1UL0HR1QXC;BRN 0144975;MFCD00022732;NSC-88884;dimethyl[(5-methyl-1H-indol-3-yl)methyl]amine;NSC88884;UNII-1UL0HR1QXC;CHEMBL4584108;SCHEMBL11493839;DTXSID10184320;STK504716;AKOS005259104;1H-Indole-3-methanamine,N,5-trimethyl-;3-Dimethylaminomethyl-5-methyl-1H-indole;DS-17426;LS-82960;N,N,5-trimethyl-1H-Indole-3-methanamine;CS-0152910;FT-0620653;C74551;M-3724;A876260;N,N-dimethyl(5-methyl-1H-indol-3-yl)methanamine;INDOLE, 3-((DIMETHYLAMINO)METHYL)-5-METHYL-

Chemical Property of N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine

Chemical Property:

• Vapor Pressure: 0.00056mmHg at 25°C
• Boiling Point: 311.5°Cat760mmHg
• PKA: 17.17±0.30(Predicted)
• Flash Point: 142.2°C
• PSA: 19.03000
• Density: 1.077g/cm³
• LogP: 2.53790
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 188.131348519
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

98%min ^*data from raw suppliers

N,N-Dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC=C2CN(C)C

Technology Process of N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine

There total 1 articles about N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine 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: 65.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-methyl-1H-indole (614-96-0) + dimethyl amine (124-40-3) → N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine (30218-58-7)

Guidance literature:

formaldehyd; 5-methyl-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: 90.0%

N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine (30218-58-7) → 5-methylindole-3-carboxaldehyde (52562-50-2)

Guidance literature:

With pyridinium chlorochromate; In N,N-dimethyl-formamide; at 100 ℃; for 0.5h;

DOI:10.3987/COM-15-13228

Reference yield:

N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine (30218-58-7) → 5-methyl-DL-tryptophan (951-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene; diethyl ether; sodium ethylate / Behandeln des Reaktionsprodukts in Aether mit wss. H₂SO₄ und Hydrieren in Aethanol an Raney-Nickel bei 100grad/118 at

2: H₂O

With diethyl ether; water; sodium ethanolate; toluene;

upstream raw materials:

formaldehyd

5-methyl-1H-indole

dimethyl amine

Downstream raw materials:

5-methyl-DL-tryptophan

acetylamino-(5-methyl-indol-3-ylmethyl)-malonic acid diethyl ester

2-(5-methyl-1H-indol-3-yl)acetonitrile

5-methylindole-3-carboxaldehyde

Refernces

• 1、 Nair, Vaishnavi N.,Kojasoy, Volga,Laconsay, Croix J.,Kong, Wang Yeuk,Tantillo, Dean J.,Tambar, Uttam K.. "Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides". supporting information. p. 9016 - 9025. Retrieved 2021/06/30.
• 2、 Grugel, Christian P.,Breit, Bernhard. "Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles". supporting information. p. 5798 - 5802. Retrieved 2019/06/08.