1H-Indole-2-carbaldehyde

Base Information

• Chemical Name: 1H-Indole-2-carbaldehyde
• CAS No.: 19005-93-7
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29339900
• European Community (EC) Number: 626-833-5
• NSC Number: 71792
• UNII: R5N9CD7DLM
• DSSTox Substance ID: DTXSID50172468
• Nikkaji Number: J1.035.660A
• Wikidata: Q72482961
• ChEMBL ID: CHEMBL223708
• Mol file: 19005-93-7.mol

Synonyms:1H-Indole-2-carbaldehyde;19005-93-7;Indole-2-carboxaldehyde;indole-2-carbaldehyde;1H-Indole-2-carboxaldehyde;2-FORMYLINDOLE;457899-31-9;MFCD03001425;R5N9CD7DLM;CHEMBL223708;(E)-(2H-Indol-2-ylidene)methanol;NSC-71792;Indolaldehyd;formyl indole;indole aldehyde;2-indolealdehyde;2-formyl indole;NSC71792;indol-2-carbaldehyde;NSC 71792;2-Hydroxymethylenindol;Indole 2-carboxaldehyde;1H-indole-2-carbaldehyd;UNII-R5N9CD7DLM;NCIOpen2_000583;SCHEMBL98455;1H-Indole-2-carbaldehyde #;Indole-2-carboxaldehyde, 97%;SCHEMBL9936320;DTXSID50172468;(Z)-(2H-Indol-2-ylidene)methanol;BDBM50037781;AKOS000302910;AB12824;AC-4322;CF-0774;CS-W016366;HY-W015650;457899-32-0;AM803433;SY042244;BB 0219951;FT-0660338;I0852;EN300-118077;AN-970/40920420;W-206402;Z1203160203

Chemical Property of 1H-Indole-2-carbaldehyde

Chemical Property:

• Appearance/Colour: White to tan solid, powder, crystals, crystalline powder and / or chunks
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Melting Point: 138-142 °C
• Refractive Index: 1.729
• Boiling Point: 339.071 °C at 760 mmHg
• PKA: 15.05±0.30(Predicted)
• Flash Point: 166.84 °C
• PSA: 32.86000
• Density: 1.279 g/cm³
• LogP: 1.98040
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Solubility.: Soluble in Methanol.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

1H-Indole-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C=O
• Uses: Indole-2-carboxaldehyde is a useful starter in indole and natural product chemistry.

Technology Process of 1H-Indole-2-carbaldehyde

There total 42 articles about 1H-Indole-2-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: 95.0%

N-methoxy-N-methyl-1H-indole-2-carboxamide (156571-69-6) → 1H-indol-2-ylcarboxaldehyde (19005-93-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -30 ℃; for 1h;

DOI:10.1016/S0040-4020(01)80649-9

Reference yield: 90.0%

6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione (58881-41-7) → 1H-indol-2-ylcarboxaldehyde (19005-93-7) + 2-(hydroxymethyl)indole (24621-70-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

Reference yield: 89.0%

indolylacetic acid (32588-36-6) → 1H-indol-2-ylcarboxaldehyde (19005-93-7)

Guidance literature:

With potassium carbonate; In chloroform; at 20 ℃; for 24h; Irradiation; Inert atmosphere;

DOI:10.1021/acs.joc.9b01759

upstream raw materials:

2-(hydroxymethyl)indole

Indole-2-carbonyl chloride

methoxybenzene

formic acid ethyl ester

Downstream raw materials:

[1-(1H-Indol-2-yl)-meth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine

1-(2-iodobenzyl)indole-2-carbaldehyde

9H-pyrrolo<1,2-a>indole

(Z)-5-indoline-2-ylmethylene-4-methyloxy-3-phenylfuran-2(5H)-one

Refernces

• 1、 Franke,Roeder. "Synthesis of 3-(2-indolyl)acrylic acid derivatives". . p. 975 - 979. Retrieved 1977.
• 2、 Tan, Yu Jia,Li, Ming,Gunawan, Gregory Adrian,Nyantakyi, Samuel Agyei,Dick, Thomas,Go, Mei-Lin,Lam, Yulin. "Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility". supporting information. p. 704 - 712. Retrieved 2020/11/30.
• 3、 Chelvam, Venkatesh,Dudhe, Premansh,Krishnan, Mena Asha,Pathak, Biswarup,Roy, Diptendu,Venkatasubbaiah, Krishnan,Yadav, Kratika. "Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation". supporting information. p. 1453 - 1463. Retrieved 2021/07/02.