41910-64-9

Basic information

• Product Name: 4-Chloroindoline
• Synonyms: 4-CHLORO-2,3-DIHYDRO-1H-INDOLE;4-CHLORO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;4-CHLOROINDOLINE;BUTTPARK 120\07-96;D-3-Chlorophenylglycine;4-CHLOROINDOLINE ,99%;1H-Indole, 4-chloro-2,3-dihydro-;4-Chloroindoline 97%
• CAS NO: 41910-64-9
• Molecular Formula: C8H8ClN
• Molecular Weight: 153.61
• EINECS: 255-586-2
• Product Categories: Indoline & Oxindole
• Mol File: 41910-64-9.mol

Chemical Properties

• Boiling Point: 260 °C at 760 mmHg
• Flash Point: 111 °C
• Appearance: /
• Density: 1.214 g/cm³
• Vapor Pressure: 0.0126mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.26±0.20(Predicted)
• CAS DataBase Reference: 4-Chloroindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroindoline(41910-64-9)
• EPA Substance Registry System: 4-Chloroindoline(41910-64-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 41910-64-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloroindoline is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure and reactivity facilitate the creation of diverse medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chloroindoline serves as an intermediate for the synthesis of agrochemicals, aiding in the production of pesticides, herbicides, and other crop protection agents to ensure agricultural productivity and sustainability.
Used in Organic Compounds Synthesis:
4-Chloroindoline is utilized as an intermediate in the synthesis of a wide range of organic compounds, showcasing its versatility in organic chemistry and its ability to contribute to the development of new chemical entities.
Used in Research and Development:
4-Chloroindoline plays a crucial role in research and development, where it is employed for the production and study of various organic compounds. Its unique properties make it an essential tool in advancing scientific knowledge and innovation in material science and related fields.

InChI:InChI=1/C8H8ClN/c9-7-2-1-3-8-6(7)4-5-10-8/h1-3,10H,4-5H2

Upstream product

• 100376-53-2 2-(2-amino-6-chlorophenyl)ethyl alcohol 
• 25235-85-2 4-chloro-1H-indole 
• 83-42-1 6-chloro-2-nitrotoluene 
• 102493-68-5 2-(2-chloro-6-nitrophenyl)-ethanol 
• 20870-77-3 4-chloroindolin-2-one 
• 64-19-7 acetic acid 

Downstream Products

• 102493-70-9 N-benzyl-4-chloro-2,3-dihydroindole 
• 102493-72-1 N-benzyl-4-chloro-5-(2-nitropropen-1-yl)-2,3-dihydroindole 
• 102493-80-1 N-benzyl-4-chloro-5-(2-nitrobuten-1-yl)-2,3-dihydroindole 
• 25235-85-2 4-chloro-1H-indole 
• 885278-80-8 indoline-4-carbonitrile 
• 1620581-31-8 2-(5-((4-chloroindolin-1-yl)sulfonyl)-2-methoxyphenyl)-2-isobutyl-4-methylpentanenitrile 
• 102493-81-2 1-(1-Benzyl-4-chloro-2,3-dihydro-1H-indol-5-ylmethyl)-propylamine 
• 102493-73-2 2-(1-Benzyl-4-chloro-2,3-dihydro-1H-indol-5-yl)-1-methyl-ethylamine 
• 102493-71-0 N-benzyl-4-chloro-2,3-dihydroindole-5-carboxaldehyde 

Relevant articles and documents

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Re-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C?H/C?N Bond Cleavage

Described herein are rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C?H/C?N bond cleavage, which provide rapid access to fused-ring pyrroloindolone derivatives. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C?H activation reactions, enabled by the unique catalytic trio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

Discovery of a novel series of indoline carbamate and indolinylpyrimidine derivatives as potent GPR119 agonists

GPR119 has emerged as an attractive target for anti-diabetic agents. We identified a structurally novel GPR119 agonist 22c that carries a 5-(methylsulfonyl)indoline motif as an early lead compound. To generate more potent compounds of this series, structural modifications were performed mainly to the central alkylene spacer. Installation of a carbonyl group and a methyl group on this spacer significantly enhanced agonistic activity, resulting in the identification of 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]propyl 7-fluoro-5-(methylsulfonyl)-2,3-dihydro-1H-indole-1-carboxylate (20). To further expand the chemical series of indoline-based GPR119 agonists, several heterocyclic core systems were introduced as surrogates of the carbamate spacer that mimic the presumed active conformation. This approach successfully produced an indolinylpyrimidine derivative 37, 5-(methylsulfonyl)-1-[6-({1-[3-(propan-2- yl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl}oxy)pyrimidin-4-yl]-2, 3-dihydro-1H-indole, which has potent GPR119 agonist activity. In rat oral glucose tolerance tests, these two indoline-based compounds effectively lowered plasma glucose excursion and glucose-dependent insulin secretion after oral administration.

NOVEL P2X7R ANTAGONISTS AND THEIR USE

The present application is directed to novel P2X7R antagonists that are N- indol-3-yl-acetamide and N-azaindol-3-yl-acetamide compounds, pharmaceutical compositions comprising the same and their use for the prophylactic or therapeutic treatment of diseases mediated by P2X7R activity.

NOVEL P2X7R ANTAGONISTS AND THEIR USE

The present application is directed to novel P2X7R antagonists that are lndol-3 carboxamide and azaindol-3 carboxamide compounds, pharmaceutical compositions comprising the same and their use for the prophylactic or therapeutic treatment of diseases mediated by P2X7R activity.

Discovery of novel N -β- d -Xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes

A novel series of N-linked β-d-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) in a cell-based assay. Of these, the 4-chloro-3-(4-cyclopropylbenzyl) -1-(β-d-xylopyranosyl)-1H-indole 19m was found to be the most potent inhibitor, with an EC50 value similar to that of the natural SGLT2 inhibitor phlorizin. Further studies in Sprague-Dawley (SD) rats indicated that 19m significantly increased urine glucose excretion in a dose-dependent manner with oral administration. The antihyperglycemic effect of 19m was also observed in streptozotocin (STZ) induced diabetic SD rats. These results described here are a good starting point for further investigations into N-glycoside SGLT2 inhibitors.

CHEMICAL COMPOUNDS

The invention is directed to substituted indoline derivatives. Specifically, the invention is directed to compounds according to Formula I wherein R1, R2 and R3 are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, ocular diseases, and diseases associated with activated unfolded protein response pathways, such as Alzheimer?s disease, stroke, Type 1 diabetes Parkinson disease, Huntington?s disease, amyotrophic lateral sclerosis, myocardial infarction, cardiovascular disease, atherosclerosis, and arrhythmias, and more specifically cancers of the breast, colon, pancreatic, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Novel SGLT inhibitors

Novel compounds of formula (A) or a pharmaceutically acceptable salt thereof: wherein symbols are as defined in claims, which are useful as SGLT inhibitors and for treatment of diabetes and related diseases.

Indole derivatives

Novel indole derivatives of formula (I) or a pharmaceutically acceptable salt thereof: wherein R1 is fluorine, or chlorine, and R2 is hydrogen, or fluorine, which are SGLT inhibitors and are useful for treatment or prevention of diabetes and related conditions.