9H-Pyrido[3,4-B]indole

Base Information

• Chemical Name: 9H-Pyrido[3,4-B]indole
• CAS No.: 244-63-3
• Molecular Formula: C11H8 N2
• Molecular Weight: 168.198
• Hs Code.: 29339900
• European Community (EC) Number: 205-959-0
• NSC Number: 84417
• UNII: 94HMA1I78O
• DSSTox Substance ID: DTXSID2021070
• Nikkaji Number: J1.605.351A,J10.931B
• Wikipedia: Beta-Carboline
• Wikidata: Q414226
• Pharos Ligand ID: SSCBVNNDG2KC
• Metabolomics Workbench ID: 42129
• ChEMBL ID: CHEMBL275224
• Mol file: 244-63-3.mol

Synonyms:beta-carboline;norharman;norharman hydrochloride;norharmane;norhormane

Chemical Property of 9H-Pyrido[3,4-B]indole

Chemical Property:

• Appearance/Colour: light yellow crystalline
• Vapor Pressure: 5.62E-06mmHg at 25°C
• Melting Point: 199-201 °C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 391.3 °C at 760 mmHg
• PKA: 15.44±0.30(Predicted)
• Flash Point: 182.1 °C
• PSA: 28.68000
• Density: 1.301 g/cm³
• LogP: 2.71610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: 2693g/L(17 oC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 168.068748264
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

≥98% ^*data from raw suppliers

Norharmane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: other cyclic peptide (other cyclic peptide)
• Canonical SMILES: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
• General Description: 9H-Pyrido[3,4-b]indole, also known as β-carboline or norharman, is a heterocyclic alkaloid that serves as a core structure for various derivatives, including bromo-β-carbolines. These derivatives are synthesized via electrophilic aromatic substitution, often using N-bromosuccinimide (NBS), and exhibit potential applications as photosensitizers in mass spectrometry. The reactivity and regioselectivity of bromination are influenced by substituents, molar ratios, and reaction conditions, with computational methods aiding in predicting electronic properties and reaction outcomes.

Technology Process of 9H-Pyrido[3,4-B]indole

There total 85 articles about 9H-Pyrido[3,4-B]indole 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%

tetrahydrobetacarboline (16502-01-5) → betacarboline (244-63-3)

Guidance literature:

With palladium 10% on activated carbon; In para-xylene; at 145 ℃; for 72h;

DOI:10.1002/anie.201303347

Reference yield: 95.0%

Tryptoline hydrochloride (58911-02-7) → betacarboline (244-63-3)

Guidance literature:

With 5 mol% Pd/C; lithium carbonate; In ethanol; at 150 ℃; for 1h; Sealed tube; Microwave irradiation;

DOI:10.1002/ejoc.201301580

Reference yield: 94.0%

6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole (25797-02-8) → betacarboline (244-63-3)

Guidance literature:

With palladium on activated carbon; In diphenylether; at 210 ℃; for 0.66h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00323

upstream raw materials:

tetrahydrobetacarboline

harmane

1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

9-benzyl-9H-pyrido<3,4-b>indole

Downstream raw materials:

2-(3-trimethylammonio-propyl)-9H-β-carbolinium; dibromide

phenyl(9H-pyrido[3,4-b]indol-9-yl)methanone

9-benzyl-9H-pyrido<3,4-b>indole

9-methylnorharmane

Refernces

Synthesis and isolation of bromo-β-carbolines obtained by bromination of β-carboline alkaloids

10.1002/jhet.5570380512

The study focuses on the synthesis and isolation of bromo-β-carbolines, which are derivatives of β-carboline alkaloids. The researchers used N-bromosuccinimide (NBS) as the brominating agent to induce electrophilic aromatic substitution in various β-carbolines, including nor-harmane, harmane, harmine, harmol, and 7-acetylharmol. The purpose of using these chemicals was to explore the behavior of substituted β-carbolines, prepare nitro-β-carbolines and bromo-β-carbolines, and investigate their potential use as matrices (photosensitizers) in matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry (uv-maldi-tof ms). The study also aimed to understand the effects of substituents on the acid-base properties and electronic excited states of these molecules. The researchers compared the use of NBS in solution and in solid state, and employed semiempirical AM1 and PM3 calculations to predict reactivity in terms of molecular orbital energies and charge density. The results provided insights into the regioselectivity of bromination and the influence of the β-carboline/NBS molar ratio and reaction time on product selectivity.