Cas no 87802-11-7 (Methyl 5-chloro-1H-indole-2-carboxylate)

Methyl 5-chloro-1H-indole-2-carboxylate is a versatile indole derivative widely used as a key intermediate in organic synthesis and pharmaceutical research. This compound features a chloro-substituted indole core with an ester functional group at the 2-position, offering excellent reactivity for further derivatization. Its high purity and stability make it suitable for applications in medicinal chemistry, particularly in the development of bioactive molecules and heterocyclic compounds. The presence of both electron-withdrawing (chloro) and electron-donating (ester) groups enhances its utility in cross-coupling reactions and other transformations. It is commonly employed in the synthesis of potential drug candidates, agrochemicals, and advanced materials.
Methyl 5-chloro-1H-indole-2-carboxylate structure
87802-11-7 structure
Product Name:Methyl 5-chloro-1H-indole-2-carboxylate
CAS No:87802-11-7
MF:C10H8ClNO2
MW:209.629021644592
MDL:MFCD04972050
CID:720837
PubChem ID:4777711
Update Time:2025-07-02

Methyl 5-chloro-1H-indole-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 5-chloro-1H-indole-2-carboxylate
    • 1H-INDOLE-2-CARBOXYLIC ACID,5-CHLORO-,METHYL ESTER
    • 5-CHLOROINDOLE-2-CARBOXYLIC ACID METHYL ESTER
    • 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
    • METHYL 5-CHLOROINDOLE-2-CARBOXYLATE
    • DB-058151
    • CS-0150776
    • AKOS004116680
    • RS-0322
    • DTXSID40406441
    • C-4625
    • MFCD04972050
    • MB03385
    • SCHEMBL3963537
    • 87802-11-7
    • MDL： MFCD04972050
    • Inchi： 1S/C10H8ClNO2/c1-14-10(13)9-5-6-4-7(11)2-3-8(6)12-9/h2-5,12H,1H3
    • InChI Key： WGAOEHZSJWVLBY-UHFFFAOYSA-N
    • SMILES： O=C(C1NC2C(=CC(=CC=2)Cl)C=1)OC

Computed Properties

  • Exact Mass: 209.02400
  • Monoisotopic Mass: 209.0243562g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 234
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.1
  • Topological Polar Surface Area: 42.1?2

Experimental Properties

  • Density: 1.4±0.1 g/cm3
  • Boiling Point: 365.5±22.0 °C at 760 mmHg
  • Flash Point: 174.8±22.3 °C
  • Refractive Index: 1.647
  • PSA: 42.09000
  • LogP: 2.60790
  • Vapor Pressure: 0.0±0.8 mmHg at 25°C

Methyl 5-chloro-1H-indole-2-carboxylate Security Information

Methyl 5-chloro-1H-indole-2-carboxylate Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Methyl 5-chloro-1H-indole-2-carboxylate Pricemore >>

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Methyl 5-chloro-1H-indole-2-carboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Xylene ;  2 h, 140 °C
Reference
Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry
Ranasinghe, Nadeesha; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(6), 1740-1742

Production Method 2

Reaction Conditions
1.1 Reagents: Iodobenzene diacetate Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: Toluene ;  3 h, reflux
Reference
[Fe(F20TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F20TPP)(NAr)](PhI=NAr)}+. Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations
Liu, Yungen; et al, Chemistry - An Asian Journal, 2015, 10(1), 100-105

Production Method 3

Reaction Conditions
1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  2.5 h, reflux
Reference
Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile
Jiang, Hai-Xia; et al, Organic & Biomolecular Chemistry, 2014, 12(21), 3446-3458

Production Method 4

Reaction Conditions
1.1 Reagents: Diisopropylethylamine Catalysts: Triphenylphosphine ,  Dichlorobis(triphenylphosphine)palladium Solvents: Methanol ,  Tetrahydrofuran ;  10 atm, rt; 20 h, 110 °C
Reference
Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles
Vieira, Tiago O.; et al, Organic Letters, 2008, 10(21), 4899-4901

Production Method 5

Reaction Conditions
1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  24 h, 20 °C
Reference
Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium formate ,  Sodium bicarbonate ,  Tetrabutylammonium chloride ,  Sodium chloride Catalysts: Palladium diacetate ;  rt; 1 h; cooled
1.2 Solvents: Acetic anhydride ;  overnight, reflux
Reference
Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and indoles
Tullberg, Erik; et al, Synthesis, 2006, (7), 1183-1189

Production Method 7

Reaction Conditions
1.1 Catalysts: Silver triflate Solvents: Dimethylformamide ;  1 min, rt; 15 min, 120 °C
Reference
Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations
Rode, Navnath D.; et al, Journal of Organic Chemistry, 2018, 83(12), 6354-6362

Production Method 8

Reaction Conditions
1.1 -
1.2 -
1.3 -
2.1 Catalysts: Silver triflate Solvents: Dimethylformamide ;  1 min, rt; 15 min, 120 °C
Reference
Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations
Rode, Navnath D.; et al, Journal of Organic Chemistry, 2018, 83(12), 6354-6362

Production Method 9

Reaction Conditions
1.1 5 h, 90 °C
2.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  24 h, 20 °C
Reference
Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

Production Method 10

Reaction Conditions
1.1 Reagents: Sodium Solvents: Methanol ;  -10 °C
2.1 Solvents: Xylene ;  2 h, 140 °C
Reference
Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry
Ranasinghe, Nadeesha; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(6), 1740-1742

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium carbonate ,  Potassium iodide Solvents: Acetone ;  12 h, 60 °C
2.1 rt → 120 °C; 12 h, 120 °C
3.1 Reagents: Iodine ;  60 min, rt
Reference
Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

Production Method 12

Reaction Conditions
1.1 Reagents: Sulfuric acid
Reference
Study of 5-endro-trig radical cyclisations, application towards new syntheis of Lycorine, synthesis of new DNA intercalating-alkylating agents, analogues to Duocarmycins
Dauge, Delfine, 2005, , ,

Production Method 13

Reaction Conditions
1.1 Reagents: Thionyl chloride Solvents: Methanol ;  cooled; 4 h, 70 °C
Reference
Synthesis and biological evaluation of novel phenylpropenoyl-amino acid derivatives
Gao, Sufan; et al, Youji Huaxue, 2019, 39(7), 1953-1961

Production Method 14

Reaction Conditions
1.1 Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: 1,2-Dichloroethane ;  rt → reflux; 24 h, reflux
Reference
[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source
Liu, Yungen; et al, Chemical Communications (Cambridge, 2010, 46(37), 6926-6928

Production Method 15

Reaction Conditions
1.1 rt; rt → 60 °C; 0.5 h, 60 °C
Reference
Simple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes
Narayana, B.; et al, Organic Chemistry: An Indian Journal, 2006, 2(1-3), 5-9

Production Method 16

Reaction Conditions
1.1 Reagents: Cesium carbonate Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ;  rt; 16 h, rt → 100 °C; 100 °C → rt
1.2 Solvents: Ethyl acetate ,  Water ;  rt
Reference
Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters
Zhu, Zhiqiang; et al, European Journal of Organic Chemistry, 2014, 2014(3), 511-514

Production Method 17

Reaction Conditions
1.1 Reagents: Iodine ;  60 min, rt
Reference
Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

Production Method 18

Reaction Conditions
1.1 Solvents: Methanol ;  reflux
2.1 Catalysts: Sulfuric acid Solvents: Methanol ;  2.5 h, reflux
Reference
Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile
Jiang, Hai-Xia; et al, Organic & Biomolecular Chemistry, 2014, 12(21), 3446-3458

Production Method 19

Reaction Conditions
1.1 rt → 120 °C; 12 h, 120 °C
2.1 Reagents: Iodine ;  60 min, rt
Reference
Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

Production Method 20

Reaction Conditions
1.1 Solvents: Toluene ;  reflux
1.2 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Ethanol ,  Water ;  5 min, 0 °C; 0.5 h, 0 °C
1.3 Reagents: Sodium azide Solvents: Water ;  15 min, 0 °C; 3 h, 0 °C
2.1 Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: 1,2-Dichloroethane ;  rt → reflux; 24 h, reflux
Reference
[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source
Liu, Yungen; et al, Chemical Communications (Cambridge, 2010, 46(37), 6926-6928

Production Method 21

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  1 h, 60 °C
1.2 12 h, 60 °C
2.1 5 h, 90 °C
3.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  24 h, 20 °C
Reference
Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

Production Method 22

Reaction Conditions
1.1 Catalysts: Rhodium, tetrakis[μ-(2,2,3,3,4,4,4-heptafluorobutanoato-κO:κO′)]di-, (Rh-Rh) ;  rt → 60 °C; 16 h, 60 °C; 60 °C → rt
Reference
Intramolecular C-H Amination Reactions: Exploitation of the Rh2(II)-Catalyzed Decomposition of Azidoacrylates
Stokes, Benjamin J.; et al, Journal of the American Chemical Society, 2007, 129(24), 7500-7501

Production Method 23

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ;  20 min, -20 °C; -20 °C → -10 °C; 4 h, -10 °C
2.1 Catalysts: Rhodium, tetrakis[μ-(2,2,3,3,4,4,4-heptafluorobutanoato-κO:κO′)]di-, (Rh-Rh) ;  rt → 60 °C; 16 h, 60 °C; 60 °C → rt
Reference
Intramolecular C-H Amination Reactions: Exploitation of the Rh2(II)-Catalyzed Decomposition of Azidoacrylates
Stokes, Benjamin J.; et al, Journal of the American Chemical Society, 2007, 129(24), 7500-7501

Methyl 5-chloro-1H-indole-2-carboxylate Raw materials

Methyl 5-chloro-1H-indole-2-carboxylate Preparation Products

Methyl 5-chloro-1H-indole-2-carboxylate Related Literature

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