2-Methylindole-3-carboxaldehyde

Base Information

• Chemical Name: 2-Methylindole-3-carboxaldehyde
• CAS No.: 5416-80-8
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 2933.99
• European Community (EC) Number: 226-512-6
• NSC Number: 11895
• UNII: R0Y4EK4FX7
• DSSTox Substance ID: DTXSID1063853
• Nikkaji Number: J36.865B
• Wikidata: Q63392569
• Mol file: 5416-80-8.mol

Synonyms:5416-80-8;2-Methylindole-3-carboxaldehyde;2-Methyl-1H-indole-3-carbaldehyde;3-Formyl-2-methylindole;2-Methyl-3-formylindole;1H-Indole-3-carboxaldehyde, 2-methyl-;Indole-3-carboxaldehyde, 2-methyl-;MFCD00012077;R0Y4EK4FX7;EINECS 226-512-6;2-Methyl-1H-indole-3-carboxaldehyde;NSC 11895;NSC-11895;2-methylindole-3-carbaldehyde;NSC11895;UNII-R0Y4EK4FX7;BIDD:GT0605;SCHEMBL248974;2-Methyl-3-formyl-1H-indole;DTXSID1063853;BCP27593;STK041022;2-Methyl-1H-indole-3-carbaldehyde #;AKOS000118949;2-Methylindole-3-carboxaldehyde, 97%;CS-W007520;PS-3273;NCGC00335106-01;AC-23428;SY018466;AM20060663;FT-0613060;FT-0659582;M1485;EN300-18130;A15638;M-3999;AB01327611-02;Q63392569;Z57197606

Chemical Property of 2-Methylindole-3-carboxaldehyde

Chemical Property:

• Appearance/Colour: Brown powder
• Vapor Pressure: 6.66E-05mmHg at 25°C
• Melting Point: 200-201 °C(lit.)
• Refractive Index: 1.698
• Boiling Point: 344.3 °C at 760 mmHg
• PKA: 16.08±0.30(Predicted)
• Flash Point: 169.9 °C
• PSA: 32.86000
• Density: 1.226 g/cm³
• LogP: 2.28880
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

98% ^*data from raw suppliers

2-Methylindole-3-carboxaldehyde >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1)C=O
• Uses: Reactant for preparation of:? ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1? ;Fluorescent sensors (BODIPY)2? ;Antimicrobial agents against methicillin-resistant Staphylococcus aureus3? ;G protein-coupled receptor CRTh2 antagonists4? ;Inhibitors of PI3 kinase-α5? ;Antitubercular agents6? ;Anti-inflammatory agents7? ;Mycobacterium tuberculosis protein tyrosine phosphatase B8? ;Glucocorticoid receptor ligands9? ;Agents stimulating neurite outgrowth10 Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsFluorescent sensors (BODIPY)Antimicrobial agents against methicillin-resistant Staphylococcus aureusG protein-coupled receptor CRTh2 antagonistsInhibitors of PI3 kinase-αAntitubercular agentsAnti-inflammatory agentsMycobacterium tuberculosis protein tyrosine phosphatase BGlucocorticoid receptor ligandsAgents stimulating neurite outgrowth

Technology Process of 2-Methylindole-3-carboxaldehyde

There total 40 articles about 2-Methylindole-3-carboxaldehyde 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: 96.0%

2-methyl-1H-indole (95-20-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-methyl-1H-indole-3-carbaldehyde (5416-80-8)

Guidance literature:

With trichlorophosphate;

Reference yield: 94.0%

1,3-diacetyl-2-(2-methylindol-3-yl)-4-imidazoline (63151-48-4) → 2-methyl-1H-indole-3-carbaldehyde (5416-80-8)

Guidance literature:

DOI:10.1016/0040-4020(80)80230-4

Reference yield: 81.0%

2-methyl-1H-indole (95-20-5) + Glyoxilic acid (298-12-4) → 2-methyl-1H-indole-3-carbaldehyde (5416-80-8)

Guidance literature:

With sodium perchlorate; aniline; In water; dimethyl sulfoxide; at 20 ℃; for 11h; Electrochemical reaction;

DOI:10.1021/acs.orglett.9b01971

upstream raw materials:

2-methyl-1H-indole

diethyl ether

n-pentyl formate

sodium ethanolate

Downstream raw materials:

tris(2-methyl-1H-indol-3-yl)methane

o-acetylamino-benzoic acid

1-(4-bromobenzyl)-3-formyl-2-methyl-1H-indole

1-(4-fluorobenzyl)-3-formyl-2-methyl-1H-indole

Refernces

• 1、 Bellamkonda, Yagna Narayana,Vijaya Chamundeeswari. "Synthesis, spectroscopic, computational and drug docking studies of 1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde". . p. 613 - 626. Retrieved 2019.
• 2、 Yadav, Sonu,Ramasastry. "Palladium-catalysed annulative allylic alkylation for the synthesis of benzannulated heteroarenes". supporting information. p. 77 - 80. Retrieved 2021/01/13.
• 3、 Ming, Yong-Chao,Lv, Xue-Jiao,Liu, Ming,Liu, Yan-Kai. "Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals". supporting information. p. 6515 - 6519. Retrieved 2021/09/02.