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

Base Information

• Chemical Name: Indole, 5-bromo-3-(dimethylamino)methyl-
• CAS No.: 830-93-3
• Molecular Formula: C11H13BrN2
• Molecular Weight: 253.142
• Hs Code.: 2933990090
• European Community (EC) Number: 624-136-0
• NSC Number: 73386
• DSSTox Substance ID: DTXSID80232120
• Nikkaji Number: J41.032B
• Wikidata: Q72456664
• ChEMBL ID: CHEMBL1253697
• Mol file: 830-93-3.mol

Synonyms:5-Bromogramine;830-93-3;1-(5-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine;INDOLE, 5-BROMO-3-(DIMETHYLAMINO)METHYL-;5-bromogramine crystalline;MFCD00055980;NSC 73386;5-bromo-3-(dimethylaminomethyl)indole;BRN 0160259;[(5-Bromo-1H-Indol-3-Yl)Methyl]Dimethylamine;1H-Indole-3-methanamine, 5-bromo-N,N-dimethyl-;4-22-00-04316 (Beilstein Handbook Reference);NSC73386;5-Bromo-N,N-dimethyl-1H-Indole-3-methanamine;SCHEMBL1196680;CHEMBL1253697;DTXSID80232120;AMY25939;NSC-73386;AKOS005259245;AC-27826;BS-22636;LS-82412;CS-0204422;FT-0620158;(5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine;A19211;B-8200;EN300-203559;(5-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine;Z1269196757

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

Chemical Property:

• Appearance/Colour: White to off white crystalline powder
• Vapor Pressure: 5.6E-05mmHg at 25°C
• Melting Point: 149.5-150 °C
• Refractive Index: 1.655
• Boiling Point: 346.9 °C at 760 mmHg
• PKA: 16.04±0.30(Predicted)
• Flash Point: 163.6 °C
• PSA: 19.03000
• Density: 1.449 g/cm³
• LogP: 2.99200
• Storage Temp.: −20°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 252.02621
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

98%min ^*data from raw suppliers

5-Bromogramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CC1=CNC2=C1C=C(C=C2)Br

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

There total 7 articles about Indole, 5-bromo-3-(dimethylamino)methyl- 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: 97.0%

5-bromo-1H-indole (10075-50-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimethyl amine (124-40-3) → N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine (830-93-3)

Guidance literature:

With acetic acid; In 1,4-dioxane; water; at 0 - 20 ℃;

Reference yield: 94.0%

5-bromo-1H-indole (10075-50-0) + dimethyl amine (124-40-3) → N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine (830-93-3)

Guidance literature:

In 1,4-dioxane; formaldehyd; water; acetic acid; at 0 ℃; for 14h;

Reference yield: 63.0%

C11H11BrN2O (1177496-99-9) → N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine (830-93-3)

Guidance literature:

C₁₁H₁₁BrN₂O; With n-butyllithium; In hexane; toluene; at 0 - 5 ℃; Inert atmosphere;

With diisobutylaluminium hydride; In hexane; toluene; at 0 - 50 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1088071

upstream raw materials:

3-(Dimethylaminomethyl)indole

5-bromo-1H-indole

formaldehyd

dimethyl amine

Downstream raw materials:

(5-bromo-1H-indol-3-yl)-acetonitrile

2-(6-bromo-1H-indol-3-yl)acetonitrile

(6-bromo-1H-indol-3-yl)acetic acid methyl ester

2-(6-bromo-1H-indol-3-yl)acetic acid

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.