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Methyl indole-5-carboxylate, also known as Methyl 1H-indole-5-carboxylate, is a substituted 1H-indole that can be prepared by the esterification of indole-5-carboxylic acid. It is a white to tan crystalline powder and has been assessed for its efficacy as a substrate for indigoid generation.

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  • 1011-65-0 Structure
  • Basic information

    1. Product Name: Methyl indole-5-carboxylate
    2. Synonyms: Methyl indole-5-carboxylate 99%;M2325G1;RARECHEM AH BS 0114;METHYL INDOLE-5-CABOXYLATE;METHYL INDOLE-5-CARBOXYLATE;METHYL 1H-INDOLE-5-CARBOXYLATE;LABOTEST-BB LT00454878;INDOLE-5-CARBOXYLIC ACID METHYL ESTER
    3. CAS NO:1011-65-0
    4. Molecular Formula: C10H9NO2
    5. Molecular Weight: 175.18
    6. EINECS: -0
    7. Product Categories: Indolines ,Indoles ,Indazoles;blocks;Carboxes;IndolesOxindoles;Acids and Derivatives;Heterocycles;Indoles and derivatives;Indole;Indoles;Simple Indoles;Boronic Acid;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indole Derivatives
    8. Mol File: 1011-65-0.mol
  • Chemical Properties

    1. Melting Point: 126-128 °C(lit.)
    2. Boiling Point: 331.7 °C at 760 mmHg
    3. Flash Point: 154.4 °C
    4. Appearance: off-white to light brown crystalline powder
    5. Density: 1.253 g/cm3
    6. Vapor Pressure: 0.000153mmHg at 25°C
    7. Refractive Index: 1.639
    8. Storage Temp.: Refrigerator
    9. Solubility: N/A
    10. PKA: 16.09±0.30(Predicted)
    11. Water Solubility: Insoluble in water.
    12. BRN: 474256
    13. CAS DataBase Reference: Methyl indole-5-carboxylate(CAS DataBase Reference)
    14. NIST Chemistry Reference: Methyl indole-5-carboxylate(1011-65-0)
    15. EPA Substance Registry System: Methyl indole-5-carboxylate(1011-65-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1011-65-0(Hazardous Substances Data)

1011-65-0 Usage

Uses

Used in Pharmaceutical Industry:
Methyl indole-5-carboxylate is used as a reactant for the biosynthesis of inhibitors of protein kinases, which are important in the development of drugs targeting various diseases, including cancer.
Used in Organic Chemistry:
Methyl indole-5-carboxylate is used as a reactant in metal-free Friedel-Crafts alkylation, a significant method in organic synthesis for the formation of carbon-carbon bonds.
Used in Synthesis of Reagents:
Methyl indole-5-carboxylate is used in the preparation of diphenylsulfonium ylides from Martin's sulfurane, which are valuable reagents in organic synthesis for the formation of carbon-carbon bonds.
Used in Cross-Dehydrogenative Coupling Reactions:
Methyl indole-5-carboxylate is used as a reactant in cross dehydrogenative coupling reactions, which are important for the formation of carbon-heteroatom bonds in organic synthesis.
Used in Synthesis of Indirubin Derivatives:
Methyl indole-5-carboxylate is used in the synthesis of indirubin derivatives, which have potential applications in the development of drugs for various therapeutic areas.
Used in Preparation of Aminoindolylacetates:
Methyl indole-5-carboxylate is used in the preparation of aminoindolylacetates, which are important intermediates in the synthesis of various pharmaceutical compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 1011-65-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,1 and 1 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1011-65:
(6*1)+(5*0)+(4*1)+(3*1)+(2*6)+(1*5)=30
30 % 10 = 0
So 1011-65-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO2/c1-13-10(12)8-2-3-9-7(6-8)4-5-11-9/h2-6,11H,1H3

1011-65-0 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L16228)  Methyl indole-5-carboxylate, 98+%   

  • 1011-65-0

  • 1g

  • 262.0CNY

  • Detail
  • Alfa Aesar

  • (L16228)  Methyl indole-5-carboxylate, 98+%   

  • 1011-65-0

  • 5g

  • 1190.0CNY

  • Detail
  • Aldrich

  • (511188)  Methylindole-5-carboxylate  99%

  • 1011-65-0

  • 511188-1G

  • 476.19CNY

  • Detail
  • Aldrich

  • (511188)  Methylindole-5-carboxylate  99%

  • 1011-65-0

  • 511188-5G

  • 1,407.86CNY

  • Detail

1011-65-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl indole-5-carboxylate

1.2 Other means of identification

Product number -
Other names Indole-5-carboxylic Acid Methyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1011-65-0 SDS

1011-65-0Relevant articles and documents

Electrochemical esterification via oxidative coupling of aldehydes and alcohols

Smeyne, Dylan,Verboom, Katherine,Bryan, Maria,LoBue, James,Shaikh, Abid

, (2021)

An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.

Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions

Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias

, p. 10776 - 10782 (2013)

Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the cross and self-esterification of alcohols to esters proceeds in good to excellent yields.

Bartoli indole synthesis on solid supports

Knepper, Kerstin,Braese, Stefan

, p. 2829 - 2832 (2003)

(Matrix presented) Bartoli indole synthesis has been performed for the first time on solid supports. Starting from Merrifield resin, immobilization of five nitro benzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic c

Silica supported palladium-phosphine as a reusable catalyst for alkoxycarbonylation and aminocarbonylation of aryl and heteroaryl iodides

Mane, Rajendra Shivaji,Sasaki, Takehiko,Bhanage, Bhalchandra Mahadeo

, p. 94776 - 94785 (2015)

Silica-supported palladium phosphine complexes were prepared for alkoxycarbonylation and aminocarbonylation of aryl iodides. These catalysts were highly efficient for the carbonylation of unprotected hydroxy-aryl, amino-aryl, iodoindole and iodopyrazole. The carbonylation of unprotected iodopyrazole is challenging and their carbonylation was achieved for the first and obtained corresponding carbonylative products are biologically active. The applicability of developed protocols tolerates wide range of functional groups with excellent yields. The catalyst was easily recovered and shows significant recyclability up to five consecutive cycles without loss in its catalytic activity and selectivity. The prepared catalysts were characterized by different techniques such as FEG-SEM, EDS, FT-IR, XPS and ICP-AES spectroscopy.

Palladium-Catalyzed, Copper(I)-Promoted Methoxycarbonylation of Arylboronic Acids with O-Methyl S-Aryl Thiocarbonates

Cao, Ya-Fang,Li, Ling-Jun,Liu, Min,Xu, Hui,Dai, Hui-Xiong

, p. 4475 - 4481 (2020)

Here, we report O-methyl S-aryl thiocarbonates as a versatile esterification reagent for palladium-catalyzed methoxycarbonylation of arylboronic acid in the presence of copper(I) thiophene-2-carboxylate (CuTC). The reaction condition is mild, and a variety of substituents including sensitive-Cl,-Br, and free-NH2 could be tolerated. Further applications in the late-stage esterification of some pharmaceutical drugs demonstrate the broad utility of this method.

Microwave-assisted synthesis and molecular recognition properties of novel indole acylhydrazone receptors

Ye, Ying,Suo, Yourui,Yang, Fang,Yang, Yongjing,Han, Lijuan

, p. 296 - 299 (2015)

Indole acylhydrazones were synthesised in high yields under microwave irradiation By using indole carboxylic acid and 1,4-benzenedialdehyde as starting materials. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Selective recognition properties of these receptors have been investigated by UV-Vis spectra titration indicating that these receptors can form 1:1 supramolecular complexes with malic acid, tartaric acid, ascorbic acid and tryptophan.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 1611 - 1615 (2021/03/03)

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

A method of synthesis of indole derivatives

-

Paragraph 0018-0021, (2022/01/10)

The present invention belongs to the field of indole synthesis technology, in order to solve the current synthesis of indole and its derivatives with ethylene glycol as raw material, the conditions are relatively harsh, the structure of the main catalyst is complex, expensive and other issues, providing a synthesis method of indole derivatives. Pt/Al2O3 catalyst supportingPt/Al2O3was prepared by impregnation with acidicAl2O3as the support, using aniline compounds, ethylene glycol, and the preparedPt/Al2O3 Catalyst for catalytic reaction, control reaction temperature of 190 °C, reaction 24h, after the end of the reaction, first add water to stir evenly, and then with dichloromethane for extraction, organic phase by rotational distillation to remove the solvent, and then with petroleum ether, ethyl acetate as the eluent column chromatography separation, you can obtain the target product. A broad spectrum of the Catalytic System ofPt/Al2O3Supported Catalysts with Good Catalytic Effect inthe Glycol Aniline Reaction was studied, and the substrate range of substituted aniline was mainly expanded.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi

supporting information, p. 15793 - 15798 (2020/10/12)

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions

Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa

supporting information, p. 1956 - 1960 (2020/04/10)

An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.

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