830-94-4

Basic information

• Product Name: 5-CHLOROGRAMINE
• Synonyms: 5-CHLOROGRAMINE;5-CHLORO-3-(DIMETHYLAMINOMETHYL)INDOLE;1H-Indole-3-MethanaMine, 5-chloro-N,N-diMethyl-;3-(dimethylaminomethyl)-5-chloro-1H-indole
• CAS NO: 830-94-4
• Molecular Formula: C₁₁H₁₃ClN₂
• Molecular Weight: 208.69
• Mol File: 830-94-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 327.421 °C at 760 mmHg
• Flash Point: 151.819 °C
• Appearance: /
• Density: 1.225 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLOROGRAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROGRAMINE(830-94-4)
• EPA Substance Registry System: 5-CHLOROGRAMINE(830-94-4)

Safety Data

• Hazardous Substances Data: 830-94-4(Hazardous Substances Data)

Usage

General Description

5-Chloro-gramine is a chemical compound with the molecular formula C9H10Cl2N2. It is a derivative of the antimalarial drug chloroquine and has shown potential antimalarial activity in vitro. 5-Chloro-gramine has also been studied for its potential use in cancer treatment, as it has been found to have cytotoxic effects on cancer cells. Additionally, it has been investigated for its antibacterial properties, particularly against drug-resistant bacteria. Despite promising initial studies, further research is needed to fully understand the pharmacological effects and potential therapeutic uses of 5-Chloro-gramine.

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 33797-51-2 eschenmoser's salt 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 936366-47-1 C₂₂H₂₂ClF₂N₂O₃P 
• 154-07-4 2-amino-3-(5-chloro-1H-indol-3-yl)propanoic acid 
• 81630-83-3 2-(5-chloro-1H-indol-3-yl)acetonitrile 

Relevant articles and documents

Substitution of the Dimethylamino Group in Gramines and One-Pot Cyclization to Tetrahydro-β-carbolines Using a Triazine-Based Activating Agent

A new method for the substitution of 3-[(dimethylamino)methyl]indoles (gramines) with malonate-based nucleophiles was developed using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) as the activating agent for the dimethylamino group. The reaction was completed in 1.5-6 h at room temperature in the presence of a tert-amine base and lithium salt. CDMT afforded superior results to methyl iodide, a common activating agent for the dimethylamino group in Mannich bases, particularly in the reactions of 1-substituted gramines. The reactivity of the possible intermediates, bis(indol-3-ylmethyl)dimethylammonium salts, was examined to obtain mechanistic insights on the reaction. This substitution method with CDMT enabled the sequential transformation of gramines: substitution with (N-alkylidene)aminomalonates followed by the Pictet-Spengler reaction under acidic conditions afforded 1,2,3,4-tetrahydro-β-carboline derivatives in one pot.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

INDOLOPYRIDINES AS INHIBITORS OF THE KINESIN SPINDLE PROTEIN (EG5 )

Compounds of formula (I), in which R1, R2, R3 and R4 have the meanings indicated in the description, are effective Eg5-inhibiting compounds with anti-proliferative and/or apoptosis inducing activity.