Cas no 883526-76-9 (1,5-Dimethyl-1H-indole-2-carbaldehyde)

1,5-Dimethyl-1H-indole-2-carbaldehyde is a versatile indole derivative characterized by its aldehyde functional group at the 2-position and methyl substituents at the 1- and 5-positions. This compound serves as a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. Its structural features enhance reactivity in condensation and cyclization reactions, making it useful for constructing heterocyclic frameworks. The electron-rich indole core and aldehyde group facilitate further functionalization, enabling precise modifications for targeted applications. High purity and stability under standard conditions ensure consistent performance in synthetic workflows. Its well-defined molecular structure also supports research in medicinal chemistry and material science.
1,5-Dimethyl-1H-indole-2-carbaldehyde structure
883526-76-9 structure
Product Name:1,5-Dimethyl-1H-indole-2-carbaldehyde
CAS No:883526-76-9
MF:C11H11NO
MW:173.211142778397
MDL:MFCD06800611
CID:1070531
PubChem ID:23004693
Update Time:2025-05-27

1,5-Dimethyl-1H-indole-2-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 1,5-Dimethyl-1H-indole-2-carbaldehyde
    • 1,5-dimethyl-1H-indole-2-carbaldehyde(SALTDATA: FREE)
    • 1,5-dimethylindole-2-carbaldehyde
    • 1,5-Dimethyl-1H-indole-2-carboxaldehyde (ACI)
    • STK501582
    • AKOS000321486
    • BS-17748
    • CS-0152918
    • D82191
    • MFCD06800611
    • ALBB-005108
    • DTXSID70629560
    • SCHEMBL4019147
    • 883526-76-9
    • MDL： MFCD06800611
    • Inchi： 1S/C11H11NO/c1-8-3-4-11-9(5-8)6-10(7-13)12(11)2/h3-7H,1-2H3
    • InChI Key： JCSJJINMAAPHJV-UHFFFAOYSA-N
    • SMILES： O=CC1N(C)C2C(=CC(C)=CC=2)C=1

Computed Properties

  • Exact Mass: 173.08400
  • Monoisotopic Mass: 173.084063974g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 204
  • 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: 2.2
  • Topological Polar Surface Area: 22?2

Experimental Properties

  • PSA: 22.00000
  • LogP: 2.29920

1,5-Dimethyl-1H-indole-2-carbaldehyde Security Information

  • Hazardous Material Identification： Xi
  • HazardClass：IRRITANT

1,5-Dimethyl-1H-indole-2-carbaldehyde 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%

1,5-Dimethyl-1H-indole-2-carbaldehyde Pricemore >>

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1,5-Dimethyl-1H-indole-2-carbaldehyde Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide
Reference
Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
Shang, Hai; et al, RSC Advances, 2016, 6(37), 30835-30839

Production Method 2

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 30 min, 0 °C
1.2 0 °C; 1 h, 0 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt
Reference
Access to tetrahydrocarbazoles and pyrrolo[3,4-b]carbazoles through sequential reactions of triazoles and indoles
Chen, Cong; et al, Organic & Biomolecular Chemistry, 2022, 20(14), 2802-2807

Production Method 3

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 0 °C → rt
1.2 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  overnight, rt
Reference
Reversal of Regioselectivity in Catalytic Arene-Ynamide Cyclization: Direct Synthesis of Valuable Azepino[4,5-b]indoles and β-Carbolines and DFT Calculations
Li, Long; et al, ACS Catalysis, 2017, 7(6), 4004-4010

Production Method 4

Reaction Conditions
1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  rt; 4 h, reflux; cooled
1.2 Reagents: Water
Reference
Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles
Wani, Imtiyaz Ahmad; et al, Organic & Biomolecular Chemistry, 2018, 16(16), 2910-2922

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Dimethylformamide ;  30 min, 25 °C
1.2 25 °C
1.3 Reagents: Water ;  25 °C
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  25 °C; 3 h, 25 °C → 40 °C; 40 °C → 25 °C
2.2 40 °C
2.3 Reagents: Ammonium chloride Solvents: Water
Reference
Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction
Xu, Shi-Ming; et al, Nature Communications, 2019, 10(1),

Production Method 6

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran
2.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane
3.1 Reagents: Sodium hydride Solvents: Dimethylformamide
Reference
Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
Shang, Hai; et al, RSC Advances, 2016, 6(37), 30835-30839

Production Method 7

Reaction Conditions
1.1 Catalysts: Sulfuric acid Solvents: Water ;  12 h, reflux
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 2 h, rt
2.2 Reagents: Ethyl acetate ;  cooled; cooled
2.3 Reagents: Water ;  cooled
3.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  rt; 4 h, reflux; cooled
3.2 Reagents: Water
Reference
Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles
Wani, Imtiyaz Ahmad; et al, Organic & Biomolecular Chemistry, 2018, 16(16), 2910-2922

Production Method 8

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
1.2 0 °C; 1 h, 0 °C → rt
1.3 Reagents: Ammonium chloride
Reference
Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis
Tan, Jian-Ping; et al, Nature Communications, 2022, 13(1),

Production Method 9

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  25 °C; 3 h, 25 °C → 40 °C; 40 °C → 25 °C
1.2 40 °C
1.3 Reagents: Ammonium chloride Solvents: Water
Reference
Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction
Xu, Shi-Ming; et al, Nature Communications, 2019, 10(1),

Production Method 10

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 4 h, rt
1.2 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  overnight
Reference
Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
Li, Long; et al, Angewandte Chemie, 2015, 54(28), 8245-8249

Production Method 11

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 2 h, rt
1.2 Reagents: Ethyl acetate ;  cooled; cooled
1.3 Reagents: Water ;  cooled
2.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Ethyl acetate ;  rt; 4 h, reflux; cooled
2.2 Reagents: Water
Reference
Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles
Wani, Imtiyaz Ahmad; et al, Organic & Biomolecular Chemistry, 2018, 16(16), 2910-2922

Production Method 12

Reaction Conditions
1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
Reference
Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes
Faltracco, Matteo; et al, Organic Letters, 2021, 23(19), 7592-7596

Production Method 13

Reaction Conditions
1.1 Reagents: 2-Iodoxybenzoic acid Solvents: Dimethyl sulfoxide ;  2 h, rt
1.2 Reagents: Water
Reference
[3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
Zhang, Kaifan; et al, Organic Letters, 2017, 19(10), 2596-2599

Production Method 14

Reaction Conditions
1.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane
2.1 Reagents: Sodium hydride Solvents: Dimethylformamide
Reference
Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
Shang, Hai; et al, RSC Advances, 2016, 6(37), 30835-30839

Production Method 15

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  30 min, 0 °C
1.2 0 °C; 1 h, 0 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 30 min, 0 °C
2.2 0 °C; 1 h, 0 °C → rt
2.3 Reagents: Ammonium chloride Solvents: Water ;  rt
Reference
Access to tetrahydrocarbazoles and pyrrolo[3,4-b]carbazoles through sequential reactions of triazoles and indoles
Chen, Cong; et al, Organic & Biomolecular Chemistry, 2022, 20(14), 2802-2807

Production Method 16

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  20 min, 0 °C
1.2 rt
1.3 Reagents: Ammonium chloride
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C
2.2 0 °C; 1 h, 0 °C → rt
2.3 Reagents: Ammonium chloride
Reference
Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis
Tan, Jian-Ping; et al, Nature Communications, 2022, 13(1),

Production Method 17

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  20 min, 0 °C
1.2 0 °C; rt
1.3 Reagents: Water
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
2.2 Reagents: Sodium hydroxide ,  Water
3.1 Reagents: 2-Iodoxybenzoic acid Solvents: Dimethyl sulfoxide ;  2 h, rt
3.2 Reagents: Water
Reference
[3 + 3] Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
Zhang, Kaifan; et al, Organic Letters, 2017, 19(10), 2596-2599

1,5-Dimethyl-1H-indole-2-carbaldehyde Raw materials

1,5-Dimethyl-1H-indole-2-carbaldehyde Preparation Products

1,5-Dimethyl-1H-indole-2-carbaldehyde Related Literature

883526-76-9 (1,5-Dimethyl-1H-indole-2-carbaldehyde) Related Products

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