5-Methoxygramine

Base Information

• Chemical Name: 5-Methoxygramine
• CAS No.: 16620-52-3
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.272
• Hs Code.: 29339900
• European Community (EC) Number: 240-669-8
• NSC Number: 88885
• UNII: J6ZN008RY8
• DSSTox Substance ID: DTXSID30168081
• Nikkaji Number: J15.685J
• Wikidata: Q72489934
• ChEMBL ID: CHEMBL3769622
• Mol file: 16620-52-3.mol

Synonyms:methoxygramine

Chemical Property of 5-Methoxygramine

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0.000126mmHg at 25°C
• Melting Point: 123-126 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 334.677 °C at 760 mmHg
• PKA: 16.70±0.30(Predicted)
• Flash Point: 156.207 °C
• PSA: 28.26000
• Density: 1.12 g/cm³
• LogP: 2.23810
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 204.126263138
• Heavy Atom Count: 15
• Complexity: 208

Purity/Quality:

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

5-Methoxygramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CC1=CNC2=C1C=C(C=C2)OC
• Uses: ? ;Reactant for preparation of dopamine D2 receptor antagonists1? ;Reactant for asymmetric preparation of ethenyl(tetrahydro)carbazoledicarboxylates via gold(I)-catalyzed intramolecular Friedel-Crafts allylic alkylation reaction2? ;Reactant for preparation of N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ols as dopamine D2-like receptor ligands3? ;Reactant for preparation of substituted N-trimethoxybenzoyl indoles, indolines, and a tetrahydroquinoline via N-aroylation with trimethoxybenzoyl chloride or anhydride as antitubulin agents4? ;Reactant for preparation of in Reactant for preparation of dopamine D2 receptor antagonistsReactant for asymmetric preparation of ethenyl(tetrahydro)carbazoledicarboxylates via gold(I)-catalyzed intramolecular Friedel-Crafts allylic alkylation reactionReactant for preparation of N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ols as dopamine D2-like receptor ligandsReactant for preparation of substituted N-trimethoxybenzoyl indoles, indolines, and a tetrahydroquinoline via N-aroylation with trimethoxybenzoyl chloride or anhydride as antitubulin agentsReactant for preparation of indolylmethanesulfonamide and its methoxy derivatives

Technology Process of 5-Methoxygramine

There total 8 articles about 5-Methoxygramine 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: 78.0%

5-methoxylindole (1006-94-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimethyl amine (124-40-3) → 5-methoxygramine (16620-52-3)

Guidance literature:

Reference yield: 77.0%

C12H14N2O2 (1177496-98-8) → 5-methoxygramine (16620-52-3)

Guidance literature:

C₁₂H₁₄N₂O₂; 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

Reference yield: 75.0%

5-methoxylindole (1006-94-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + N,N-dimethylammonium chloride (506-59-2) → 5-methoxygramine (16620-52-3)

Guidance literature:

With acetic acid; triethylamine; In 1,4-dioxane; water; at 20 ℃; for 2.5h;

DOI:10.1021/acs.joc.9b00039

upstream raw materials:

ethylmagnesium iodide

5-methoxylindole

diethyl ether

N,N-Dimethylamino acetonitrile

Downstream raw materials:

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

5-methoxyindole-3-acetonitrile

1-(5-methoxyindol-3-yl)-2-nitropropane

C₂₆H₂₇N₃O₃

Refernces

• 1、 Becker, Antonia,Breit, Bernhard,Grugel, Christian P.. "Rhodium-Catalyzed Stereoselective Cyclization of 3-Allenylindoles and N-Allenyltryptamines to Functionalized Vinylic Spiroindolenines". supporting information. p. 3788 - 3792. Retrieved 2021/05/29.
• 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.