114144-22-8

Basic information

• Product Name: 7-chloroindoline
• Synonyms: 7-chloroindoline;1H-INDOLE,7-CHLORO-2,3-DIHYDRO-;7-Chloro-2,3-dihydro-1H-indole
• CAS NO: 114144-22-8
• Molecular Formula: C₈H₈ClN
• Molecular Weight: 153.61
• Mol File: 114144-22-8.mol

Chemical Properties

• Melting Point: 41-42 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 260.6±29.0 °C(Predicted)
• Appearance: /
• Density: 1.214±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.42±0.20(Predicted)
• CAS DataBase Reference: 7-chloroindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloroindoline(114144-22-8)
• EPA Substance Registry System: 7-chloroindoline(114144-22-8)

Safety Data

• Hazardous Substances Data: 114144-22-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
7-chloroindoline is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and reactivity contribute to the development of new and effective compounds for medical and agricultural applications.
Used in Organic Synthesis:
7-chloroindoline is utilized as a valuable building block in organic synthesis, particularly for the creation of heterocyclic compounds. Its structural and reactivity properties make it an essential component in the synthesis of complex organic molecules.
Used in Materials Science:
7-chloroindoline has been studied for its potential applications in materials science, where its unique properties can be harnessed to develop new materials with specific characteristics and functions.
Used as a Precursor to Novel Dyes and Colorants:
7-chloroindoline is also used as a precursor to novel dyes and colorants, where its chemical properties can be exploited to create new and innovative colorants for various industries, such as textiles, plastics, and printing inks.

Upstream product

• 114144-23-9 1-acetyl-2,3-dihydro-7-chloroindole 
• 124-41-4 sodium methylate 
• 176097-78-2 3a,7,7-trichloro-3,3a,4,5,6,7-hexahydro-2H-indole 
• 910808-40-1 7-chloro-N-formylindoline 
• 496-15-1 1-indoline 
• 2861-59-8 N-formylindoline 
• 53924-05-3 7-chloro-1H-indole 
• 88-73-3 2-Chloronitrobenzene 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 18159-32-5 Δ¹⁽⁸⁾-hexahydroindole 

Downstream Products

• 53924-05-3 7-chloro-1H-indole 
• 1448522-88-0 1-benzyl-3-(2-(7-chloroindolin-1-yl)-2-oxoethyl)indolin-2-one 
• 1027266-25-6 {(E)-(S)-4-(7-Chloro-2,3-dihydro-indol-1-yl)-4-oxo-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

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.

Total Synthesis of (-)-Nodulisporic Acid D

A convergent total synthesis of the architecturally complex indole diterpenoid (-)-nodulisporic acid D has been achieved. Key synthetic transformations include vicinal difunctionalization of an advanced α,β-unsaturated aldehyde to form the E,F-trans-fused 5,6-ring system of the eastern hemisphere and a cascade cross-coupling/indolization protocol leading to the CDE multisubstituted indole core.

Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines

Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.

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.

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.

NOVEL 6-5 BICYCIC HETEROCYCLIC DERIVATIVE AND MEDICAL USE THEREOF

An object of the present invention is to provide a medicament as a thyroid hormone receptor ligand which is sufficient in drug efficacy and safety, and has the excellent action as a drug. The present invention provides a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof: [wherein [Chemical Formula 2] is a single bond or a double bond; A is -CH2- or -CO-; X, Y, and Z are each independently a nitrogen atom or a carbon atom; R1 is a hydrogen atom or an aralkyl group; R2 is an alkyl group or an aralkyl group, etc.; R3 is a hydrogen atom or an alkyl group, etc.; R4 is a hydrogen atom or an alkyl group; R5 is a hydrogen atom, an alkyl group or a halo lower alkyl group, etc.; R6 is a hydrogen atom or an alkyl group; R7 is a hydrogen atom, etc.; R8 is a hydrogen atom, or an alkyl group, etc.; and E is -NHCO-G-COR12, etc. (wherein G is a single bond or an alkylene group, and R12 is a hydroxy group or an alkoxy group)].

Preparation of 7-halo-indoles by thallation of N-formylindoline and their attempted use for synthesis of the right-hand segment of chloropeptin

7-Substituted (Cl, Br, I) indoles were synthesized by using thallation of N-formylindoline as a key reaction. Two precursor tripeptides for the right-hand segment of chloropeptin were synthesized by using (R)-7′-iodo and 7′-bromotryptophans derived from each 7-substituted indole (I, Br) obtained by the above procedure.

Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines

Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) α-alkylation with N,N-disilyl-protected ω-bromoamines, (c) transimination, (d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.

The Chemistry of Indoles. XXXIX. A Facile Synthetic Method for 7-Substituted Indoles

A simple four-step synthetic method for 7-iodo-, 7-bromo- and 7-chloroindole was established with high overall yield starting from 2,3-dihydroindole.Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthetized.Keywords - thallation; 7-substituted indole; regioselective metalation; 7-iodoindole; 7-bromoindole; 7-chloroindole; 7-methoxyindole; methyl 3-(indol-7-yl)acrylate; 4-(indol-7-yl)-2-methyl-3-buten-2-ol; Heck reaction