98081-84-6

Basic information

• Product Name: 6-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 6-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;AKOS JY2082773;ETHYL 6-CHLORO-1H-INDOLE-2-CARBOXYLATE;METHYL 6-CHLORO-1H-INDOLE-2-CARBOXYLATE;6-Chloro-2-indolecarboxylic acid methyl ester;6-Chloroindole-2-carboxylic acid methyl ester;6-Chloro-1H-indole-2-carboxylic acid methyl ester≥ 98.5% (HPLC)
• CAS NO: 98081-84-6
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• Product Categories: pharmacetical
• Mol File: 98081-84-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 365.5 °C at 760 mmHg
• Flash Point: 174.8 °C
• Appearance: /
• Density: 1.382 g/cm³
• Vapor Pressure: 1.56E-05mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 6-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(98081-84-6)
• EPA Substance Registry System: 6-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(98081-84-6)

Safety Data

• Hazardous Substances Data: 98081-84-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to orange solid

InChI:InChI=1/C10H8ClNO2/c1-14-10(13)9-4-6-2-3-7(11)5-8(6)12-9/h2-5,12H,1H3

Upstream product

• 102244-86-0 (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate 
• 67-56-1 methanol 
• 16732-75-5 6-chloro-1H-indole-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 104-88-1 4-chlorobenzaldehyde 
• 126690-10-6 (3-chloro-phenylamino)-acetic acid methyl ester 
• 108-42-9 3-chloro-aniline 
• 98081-76-6 C₁₀H₈ClN₃O₂ 
• 1586740-57-9 (Z)-methyl 3-(2-amino-4-chlorophenyl)-2-bromoacrylate 
• 1586740-46-6 (Z)-methyl 2-bromo-3-(4-chloro-2-nitrophenyl)acrylate 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 1609930-28-0 C₁₀H₁₁ClN₂O₂ 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 57427-81-3 4-(2,4-dichloro-benzylidene)-2-phenyl-4H-oxazol-5-one 

Downstream Products

• 20948-68-9 6-chloro-indole-2-carboxylic acid hydrazide 
• 287384-60-5 methyl 6-chloro-1-(cyanomethyl)-indole-2-carboxylate 
• 1584221-42-0 C₁₇H₁₄ClNO₂ 
• 1584221-43-1 C₁₆H₁₄ClNO 
• 1584221-45-3 C₁₆H₁₂ClNO 
• 1584221-46-4 C₂₃H₁₉ClN₂O₂S 
• 1584221-47-5 C₂₃H₂₁ClN₂O₂S 
• 1529806-92-5 9-benzyl-7-chloro-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexa-hydrospiro[pyrido[3,4-b]indole-4,2'-pyrrole] 
• 1529806-73-2 N-((1-benzyl-6-chloro-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)-prop-2-ynyl)benzenesulfonamide 
• 1584144-61-5 N-(4-(dimethylamino)phenethyl)-3-ethyl-6-chloro-1H-indole-2-carboxamide 
• 53590-59-3 6-chloro-1H-indole-2-carbaldehyde 
• 53590-58-2 (6-chloro-1H-indol-2-yl)methanol 

Relevant articles and documents

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate

An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee) and chemoselectivity (3/4>19:1 in most cases).

Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.