534595-85-2

Basic information

• Product Name: METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE
• Synonyms: METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE;CHEMPACIFIC 38155;3-Iodo-2-(methoxycarbonyl)-1H-indole
• CAS NO: 534595-85-2
• Molecular Formula: C₁₀H₈INO₂
• Molecular Weight: 301.08
• Mol File: 534595-85-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 157-159°C
• Boiling Point: 392.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.860±0.06 g/cm3(Predicted)
• PKA: 13.48±0.30(Predicted)
• CAS DataBase Reference: METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE(534595-85-2)
• EPA Substance Registry System: METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE(534595-85-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 534595-85-2(Hazardous Substances Data)

Usage

General Description

Methyl 3-iodo-1H-indole-2-carboxylate is a chemical compound with the molecular formula C11H8INO2. It is a derivative of indole, which is a heterocyclic aromatic organic compound. METHYL 3-IODO-1H-INDOLE-2-CARBOXYLATE is commonly used in organic synthesis and medicinal chemistry as a building block to create various pharmaceutical drugs and other organic compounds. It is known for its potential biological activities and is often used as a starting material in the synthesis of new compounds for pharmaceutical research. Methyl 3-iodo-1H-indole-2-carboxylate is a versatile and important chemical in the field of organic chemistry and drug development.

Upstream product

• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 1477-50-5 Indole-2-carboxylic acid 

Downstream Products

• 916180-08-0 3-iodo-1-(toluene-4-sulfonyl)-indole-2-carboxylic acid methyl ester 
• 1316759-09-7 1-methyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester 
• 1316759-11-1 1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester 
• 1316759-13-3 1-butyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester 
• 1316759-25-7 C₁₈H₁₃NO₂ 
• 1316759-26-8 C₁₉H₁₅NO₂ 
• 1316759-27-9 C₂₁H₁₉NO₂ 
• 1316759-35-9 C₁₇H₁₁NO₂ 
• 1316759-39-3 9-methyl-3-phenylpyrano[3,4-b]indol-1(9H)-one 
• 1316759-41-7 9-ethyl-3-phenylpyrano[3,4-b]indol-1(9H)-one 
• 1316759-44-0 9-butyl-3-phenylpyrano[3,4-b]indol-1(9H)-one 
• 1316759-52-0 3-phenylpyrano[3,4-b]indol-1(9H)-one 
• 1316759-22-4 methyl 3-(2-phenylethynyl)-1H-indole-2-carboxylate 

Relevant articles and documents

Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams

We report here a Ru-catalyzed enantioselective synthesis of biaryl-bridged NH lactams through asymmetric reductive amination and a spontaneous ring-closing cascade from keto esters and NH4OAc with H2 as reductant. The reaction features broad substrate generality and high enantioselectivities (up to >99percent ee). To showcase the practical utility, a highly enantioselective synthesis of 5-ethylindolobenzazepinone C, a promising antimitotic agent, has been rapidly completed. Furthermore, the amide group in the products enables versatile elaborations through directed C-H functionalization.

Flexible synthesis of isomeric pyranoindolones and evaluation of cytotoxicity towards HeLa cells

A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achieved by employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids in good to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhibitory activity against human cervix adenocarcinoma (HeLa) which revealed that three compounds exhibited activity comparable with the standard cis-platin (IC50 = 0.08 μM). Molecular docking of all the compounds in Vaccinia H1-Related (VHR) Phosphatase receptor also supported that compound 7d as the most active with a free energy of binding as ?8.27 kcal/mol. [Figure not available: see fulltext.]

Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma

A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds (7d, 7e and 7j) showed comparable proliferation inhibitory activity against the standard drug cisplatin. Compound 7d was found to be the most efficacious with IC50 value of 0.22 μM.