233-34-1

Basic information

• Product Name: 1H-BENZO(G)INDOLE
• Synonyms: 1H-BENZO(G)INDOLE;1H-Benz[g]indole;6,7-Benzindole;NSC 153687;1H-Benzo[g]indole 97%;1H-Benz[g]indole 6,7-Benzindole NSC 153687
• CAS NO: 233-34-1
• Molecular Formula: C₁₂H₉N
• Molecular Weight: 167.20656
• Mol File: 233-34-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 180-184 °C
• Boiling Point: 371.1°Cat760mmHg
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 2.26E-05mmHg at 25°C
• Refractive Index: 1.767
• PKA: 17.00±0.30(Predicted)
• CAS DataBase Reference: 1H-BENZO(G)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-BENZO(G)INDOLE(233-34-1)
• EPA Substance Registry System: 1H-BENZO(G)INDOLE(233-34-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 233-34-1(Hazardous Substances Data)

Usage

Description

1H-BENZO(G)INDOLE is an organic compound that serves as a key reactant in the preparation of various chemical compounds, including tryptophan dioxygenase inhibitors and pyridyl-ethenyl-indoles. These compounds have potential applications in the field of cancer treatment, particularly as immunomodulators.

Uses

Used in Pharmaceutical Industry:
1H-BENZO(G)INDOLE is used as a reactant for the preparation of tryptophan dioxygenase inhibitors, which are compounds that inhibit the activity of tryptophan dioxygenase, an enzyme involved in the metabolism of tryptophan. This inhibition can have potential therapeutic effects in the treatment of certain cancers.
1H-BENZO(G)INDOLE is also used as a reactant for the synthesis of pyridyl-ethenyl-indoles, which are potential anticancer immunomodulators. These compounds can modulate the immune system to enhance the body's natural defense mechanisms against cancer cells.

InChI:InChI=1/C12H9N/c1-2-4-11-9(3-1)5-6-10-7-8-13-12(10)11/h1-8,13H

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 89278-00-2 2-(1-nitronaphthalen-2-yl)acetonitrile 
• 134-32-7 1-amino-naphthalene 
• 107-21-1 ethylene glycol 
• 91165-85-4 dimethyl 1-(1-naphthyl)-1H-1,2,3-triazole-4,5-dicarboxylate 
• 6921-40-0 1-azidonaphthalene 
• 107784-16-7 (2-Bromo-naphthalen-1-yl)-carbamic acid ethyl ester 
• 771-14-2 2-bromonaphthalen-1-amine 
• 881-03-8 1-nitro-2-methylnaphthalene 
• 4995-14-6 4,5-dihydrobenzo[g]indole 
• 176853-40-0 2-<β-trans-(N,N-dimethylamino)ethenyl>-1-nitronaphthalene 
• 445262-76-0 2-(2-ethynyl-phenyl)-1H-pyrrole 
• 81945-58-6 1-(1'H-1',2',3'-triazolyl)naphthalene 
• 112011-01-5 N-(1-naphtyl)-ethenesulphenamide 

Downstream Products

• 51136-18-6 1H-benzo[g]indole-3-carboxaldehyde 
• 60336-23-4 (1H-benzo[g]indol-3-yl)-phenyl-methanone 

Relevant articles and documents

Pd-Catalyzed Regioselective Direct Double C–H Arylation of 6,7-Benzindoles

A palladium-catalyzed protocol for the first direct diarylation of 6,7-benzindoles with aryl iodides at the C4 and C5 positions was developed. The key to this strategy was the employment of pivaloyl as the directing group at the C3 position and the blocking effect at the C6 and C7 positions. The reaction proceeded very well, providing a series of diarylated 6,7-benzindoles without prefunctionalization at the reactive sites. Several examples on the unexpected monoarylation of 6,7-benzindoles at the C5 position were also presented.

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation

The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to slowly dehydrogenate ethylene glycol generating, after condensation with the amine and tautomeric equilibrium, the corresponding pyrrole-ring unsubstituted indoles.

Phenanthroline- tBuOK Promoted Intramolecular C-H Arylation of Indoles with ArI under Transition-Metal-Free Conditions

The first example of phenanthroline-tBuOK promoted intramolecular radical C-H arylation of N-(2-iodobenzyl)indoles without involvement of transition metals has been developed. A variety of substituted 6H-isoindolo [2, 1-a] indoles were prepared by a simple and efficient intramolecular cyclization using 1,10-phenanthroline in the presence of potassium tert-butoxide and chlorobenzene. This strategy provides a fast and versatile access to isoindolo[2,1-a]indole derivatives for the synthesis of pharmaceuticals and organic electroluminescent (EL) materials.