58881-45-1

Basic information

• Product Name: 1H-INDOLE-2-CARBONYL CHLORIDE
• Synonyms: 1H-INDOLE-2-CARBONYL CHLORIDE
• CAS NO: 58881-45-1
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.60304
• Mol File: 58881-45-1.mol
• Article Data: 94

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-INDOLE-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-2-CARBONYL CHLORIDE(58881-45-1)
• EPA Substance Registry System: 1H-INDOLE-2-CARBONYL CHLORIDE(58881-45-1)

Safety Data

• Hazardous Substances Data: 58881-45-1(Hazardous Substances Data)

Usage

General Description

1H-Indole-2-carbonyl chloride, also known as indole-2-carbonyl chloride, is an organic compound with the chemical formula C9H6ClNO. It is a derivative of indole and is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. 1H-INDOLE-2-CARBONYL CHLORIDE is a versatile building block in organic synthesis, particularly in the formation of indole-containing compounds. It is a reactive and versatile reagent that undergoes a variety of chemical reactions, such as nucleophilic substitution and condensation reactions, making it a valuable tool in synthetic organic chemistry. Its use in the pharmaceutical industry makes it a compound of particular interest for further study and development.

Upstream product

• 1477-50-5 Indole-2-carboxylic acid 
• 79-37-8 oxalyl dichloride 
• 68-12-2 N,N-dimethyl-formamide 
• 610-33-3 (2-nitro-phenyl)-glyoxylic acid 
• 3770-50-1 2-carbethoxyindole 

Downstream Products

• 7511-14-0 N,N-dimethyl-1H-indole-2-carboxamide 
• 69808-71-5 1H-indole-2-carboxylic acid methylamide 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 1670-84-4 1H-indole-2-carboxamide 
• 153473-49-5 1-(indolyl-2-carbonyl)-4-(2-methoxyphenyl)piperazine 
• 610282-93-4 N-allyl-N-cyclohexyl-1H-indole-2-carboxamide 
• 117614-22-9 5(S)-5-(2-indolecarbonylamino)-7-phenyl-5H-pyrimido-[5,4-d][2]benzazepine 
• 79112-20-2 2-hydroxy-5-(indole-2-carboxamido)acetophenone 
• 1094223-71-8 N-(2-bromo-4-methylphenyl)-1H-indole-2-carboxamide 
• 1315282-57-5 N-(2-bromo-4-chlorophenyl)-1H-indole-2-carboxamide 
• 1094223-82-1 N-(2-bromophenyl)-1H-indole-2-carboxamide 
• 1431758-21-2 C₁₇H₁₂N₂O 
• 1431758-22-3 C₁₈H₁₄N₂O 
• 1431758-23-4 C₁₉H₁₆N₂O 

Relevant articles and documents

Discovery and preliminary SARs of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors

Indoleamine 2,3-dioxygenase (IDO) is an important new therapeutic target for the treatment of cancer. With the aim of discovering novel IDO inhibitors, a virtual screen was undertaken and led to the discovery of the keto-indole derivative 1a endowed with an inhibitory potency in the micromolar range. Detailed kinetics were performed and revealed an uncompetitive inhibition profile. Preliminary SARs were drawn in this series and corroborated the putative binding orientation as suggested by docking.

Iron(III)-Catalyzed (4 + 2)-Cycloannulation of 2-Hydroxy Ketoxime Ethers with Indol-2-ylamides: Synthesis of Indole-Fused 2-Piperidinones

A highly regio- and diastereoselective (4 + 2)-cycloannulation process of indanone-derived 2-hydroxy ketoxime ethers with 1,4-bisnucleophilic indol-2-ylamides has been developed. In the presence of 5 mol % FeCl3, densely functionalized 2-piperidinones containing two new σ-bonds and two vicinal quaternary stereogenic centers were formed under mild reaction conditions in a one-pot operation. Moreover, most of the products directly precipitated out of the solution and were isolated by simple filtration without purification by column chromatography.

Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4] benzodiazepine and indole conjugates as anticancer agents

A series of novel pyrrolo[2,1-c][1,4]benzodia/epine (PBD) hybrids linked with indole carboxylates is described. These compounds were prepared by linking C-8 of 3 (DC-81) with an indole 2-carbonyl moiety (9) through carbon chain linkers to afford PBD hybrid agents 17-21 in good yields. Preliminary in vivo tests show that these hybrid agents have potent antitumor activity. The cytotoxic studies of the hybrid agents on human melanoma A2058 cells indicate most of the hybrids induced higher cytotoxicity, better DNA-binding ability, an increase in the apoptotic sub-G1 population, and a significant reduction in ΔΨmt relative to compound 3. In addition, DNA flow cytometric analysis shows that hybrids actively induce a marked loss of cells from the G2/M phase of the cell cycle, which progresses to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI). Thus, we suggest that the hybrid agents are potent inducers of cell apoptosis in A2058 cells.

Highly selective and sensitive fluorescent chemosensor for Hg2+ in aqueous solution

A new indole-based fluorescent chemosensor 1 was prepared and its metal ion sensing properties were investigated. It exhibits high sensitivity and selectivity toward Hg2+ among a series of metal ions in H 2O-EtOH (7:1, v/v). The association constant of the 1:1 complex formation for 1-Hg2+ was calculated to be 9.57 × 103 M-1, and the detection limit for Hg2+ was found to be 2.25 × 10-5 M. Computational results revealed that 1 and Hg2+ ion formed with a central tetrahedron-coordinated Hg 2+.

New class of benzothiophene morpholine analogues with high selectivity and affinity were designed and evaluated for anti-drug addiction

To probe the mechanism of dopamine receptors in drug addiction and look for potential new methods for treating this disease, we have designed and synthesized benzothiophene morpholine analogues that were considered as dopamine D3 receptor-selective ligands. Radioligand binding assay was used to determine the binding affinity of target compounds. Members of this class have great selectivity and binding affinity in D3 receptor. In addition, the ability of these compounds to mitigate the symptoms of addiction from opioids was investigated in animal behavior patterns, and we have found that two compounds (18a and 18d) have good affinity in the D3R and exhibit the efficacy of anti-drug addiction in morphine-dependent mice induced by naloxone.

Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.

Synthesis of Indolo[2,3- c]quinolin-6(7 H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C-H Arylation

The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C-H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provide