1-Methyl-1H-indole-3-carbaldehyde

Base Information

• Chemical Name: 1-Methyl-1H-indole-3-carbaldehyde
• CAS No.: 19012-03-4
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 29339900
• European Community (EC) Number: 242-750-3
• NSC Number: 83042
• UNII: Z612E3VMZ5
• DSSTox Substance ID: DTXSID50172483
• Nikkaji Number: J46.086I
• Wikidata: Q63409361
• ChEMBL ID: CHEMBL210779
• Mol file: 19012-03-4.mol

Synonyms:1-Methyl-1H-indole-3-carbaldehyde;19012-03-4;1-Methylindole-3-carboxaldehyde;1-methylindole-3-carbaldehyde;1H-Indole-3-carboxaldehyde, 1-methyl-;3-Formyl-1-methylindole;1-Methyl-3-formylindole;MFCD00014570;1-Methyl-indole-3-carbaldehyde;N-Methyl-3-formylindole;N-Methyl-3-indolecarboxaldehyde;Indole-3-carboxaldehyde, 1-methyl-;N-Methylindole-3-carbaldehyde;CHEMBL210779;Z612E3VMZ5;N-Methylindole-3-carboxaldehyde;EINECS 242-750-3;1-methyl-1h-indole-3-carboxaldehyde;NSC-83042;AI3-51477;3-Formyl-1-methyl-1H-indole;NSC83042;N-Methylindole-3-aldehyde;1-methylindole-3-aldehyde;D0D1KZ;NCIOpen2_001125;UNII-Z612E3VMZ5;MLS000718559;N-methyl-indol-3-carbaldehyde;SCHEMBL378958;DTXSID50172483;HMS2669I09;BCP27540;1-Methyl-1-H-indole-3-carbaldehyde;BBL010587;BDBM50182875;GEO-01854;NSC 83042;STK280622;1-methyl-1 H-indol-3-carboxaldehyde;AKOS000265019;1-Methylindole-3-carboxaldehyde, 97%;AC-6596;CS-W017947;SB15037;NCGC00245440-01;AM803434;NS-00004;SMR000290827;SY008054;A4193;BB 0255019;FT-0630302;EN300-31045;M-3998;Q63409361;Z56785556;1-methyl-1H-indole-3-carbaldehyde

Chemical Property of 1-Methyl-1H-indole-3-carbaldehyde

Chemical Property:

• Appearance/Colour: light yellow to orange or brown crystalline powder
• Vapor Pressure: 0.000356mmHg at 25°C
• Melting Point: 70-72 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 318.7 °C at 760 mmHg
• Flash Point: 146.5 °C
• PSA: 22.00000
• Density: 1.1 g/cm³
• LogP: 1.99080
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99.9% ^*data from raw suppliers

1-Methyl-1H-indole-3-carbaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)C=O
• Uses: Reactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions Reactant for synthesis of quinolinones via three-component Ugi reaction Reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture Reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins Reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents. 1-Methylindole-3-carboxaldehyde is used as a reactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions, reactant for synthesis of quinolinones via three-component Ugi reaction, reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture, reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins, reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent, reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents 1-Methylindole-3-carboxaldehyde may be used in the synthesis of (Z)-3-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile, via base-catalyzed condensation with thiophene-3-acetonitrile. It was also used in the preparation of monomer, required for the synthesis of poly(3-vinyl-1-methylindole).

Technology Process of 1-Methyl-1H-indole-3-carbaldehyde

There total 82 articles about 1-Methyl-1H-indole-3-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + methyl iodide (74-88-4) → N-methyl-3-formylindole (19012-03-4)

Guidance literature:

Indole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.75h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 96.0%

1-methylindole (603-76-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → N-methyl-3-formylindole (19012-03-4)

Guidance literature:

N,N-dimethyl-formamide; With oxalyl dichloride; at 0 ℃; for 1h;

1-methylindole; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

With sodium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 0.166667h;

DOI:10.1016/j.ejmech.2013.04.057

Reference yield: 96.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + methylene chloride (74-87-3) → N-methyl-3-formylindole (19012-03-4)

Guidance literature:

Indole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

methylene chloride; at 0 - 20 ℃;

DOI:10.1055/s-0041-1737275

upstream raw materials:

Indole-3-carboxaldehyde

dimethyl sulfate

1-methylindole

N,N-dimethyl-formamide

Downstream raw materials:

1-(4-Chloro-phenyl)-3-(1-methyl-1H-indol-3-yl)-3-[1,2,4]triazol-1-yl-propan-1-one

diphenyl(2-hydroxy-2--1-morpholinoethyl)phosphine oxide

methyl-1 (nitro-2 ethynyl)-3 indole

1-methyl-3-[(E)-2-nitrovinyl]-1H-indole

Refernces

• 1、 Bohlaender, Peggy R.,Wagenknecht, Hans-Achim. "Synthesis and evaluation of cyanine-styryl dyes with enhanced photostability for fluorescent DNA staining". . p. 7458 - 7462. Retrieved 2013.
• 2、 Aksungur, Tu??e,Ayd?ner, Burcu,Sefero?lu, Nurgül,?zkütük, Müjgan,Arslan, Leyla,Reis, Yasemin,A??k, Leyla,Sefero?lu, Zeynel. "Coumarin-indole conjugate donor-acceptor system: Synthesis, photophysical properties, anion sensing ability, theoretical and biological activity studies of two coumarin-indole based push-pull dyes". . p. 364 - 379. Retrieved 2017.
• 3、 Bakkolla, Mahesh Goud,Taduri, Ashok Kumar,Bhoomireddy, Rama Devi. "A simple and facile synthesis of novel 1,2,3-triazole substituted pyrimidine derivatives". . p. 2489 - 2497. Retrieved 2020.
• 4、 Gaur, Pankaj,Kumar, Ajay,Bhattacharyya, Shalmoli,Ghosh, Subrata. "Biomolecular recognition at the cellular level: Geometrical and chemical functionality dependence of a low phototoxic cationic probe for DNA imaging". . p. 4895 - 4900. Retrieved 2016.
• 5、 Buglioni, Laura,Mastandrea, Marco M.,Frontera, Antonio,Pericàs, Miquel A.. "Anion–π Interactions in Light-Induced Reactions: Role in the Amidation of (Hetero)aromatic Systems with Activated N-Aryloxyamides". . p. 11785 - 11790. Retrieved 2019.
• 6、 Lin, Jin-Hong,Xiao, Ji-Chang,Zhu, Yu-Rong. "Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide". supporting information. . Retrieved 2021/11/22.
• 7、 Gouthami, Dasari,Juluru, Bhaskar,Srinivas, Bandari,Suresh, Paidakula. "One-Pot Multi-Component Synthesis and Biological Evaluation of Novel Indole-Pyrimidine Derivatives as Potent Anti-Cancer and Anti-Microbial Agents". . p. 954 - 962. Retrieved 2021/08/25.