2-(1H-indol-3-yl)acetaldehyde

Base Information

• Chemical Name: 2-(1H-indol-3-yl)acetaldehyde
• CAS No.: 2591-98-2
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 2933990090
• UNII: A346H8E8WU
• DSSTox Substance ID: DTXSID90180582
• Nikkaji Number: J398.271H
• Wikipedia: Indole-3-acetaldehyde
• Wikidata: Q27102813
• Metabolomics Workbench ID: 37651
• Mol file: 2591-98-2.mol

Synonyms:2-(3-Indolyl)acetaldehyde;Indole-3-acetaldehyde(6CI,7CI,8CI);Indol-3-ylacetaldehyde;Tryptaldehyde;

Chemical Property of 2-(1H-indol-3-yl)acetaldehyde

Chemical Property:

• Vapor Pressure: 3.78E-05mmHg at 25°C
• Refractive Index: 1.651
• Boiling Point: 352.7 °C at 760 mmHg
• PKA: 16.75±0.30(Predicted)
• Flash Point: 174.9 °C
• PSA: 32.86000
• Density: 1.205 g/cm³
• LogP: 1.90930
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

2-(1H-Indol-3-yl)acetaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC=O
• Uses: Tryptaldehyde is used as plasma metabolite biomarker related to secondary hyperparathyroidism and parathyroid hormone.

Technology Process of 2-(1H-indol-3-yl)acetaldehyde

There total 30 articles about 2-(1H-indol-3-yl)acetaldehyde 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: 99.0%

2-(3-indole)-ethanol (526-55-6,930395-07-6) → indole-3-acetaldehyde (2591-98-2)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 80 ℃; for 2h;

DOI:10.1055/s-0030-1261032

Reference yield: 80.0%

2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide (132922-37-3) → indole-3-acetaldehyde (2591-98-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

Reference yield: 75.0%

Indole-3-acetic acid methyl ester (1912-33-0) → indole-3-acetaldehyde (2591-98-2)

Guidance literature:

With diisobutylaluminium hydride; In 1,2-dimethoxyethane; dichloromethane; toluene; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)96581-0

upstream raw materials:

tryptamine

3-indol-3-yl-propane-1,2-diol

3-(1,3-diphenyl-imidazolidin-2-ylmethyl)-indole

Trp

Downstream raw materials:

3-hydroxy-1,4-bis(4-hydroxyphenyl)butan-2-one

soraphinol A

3-hydroxy-1,4-di(1H-indol-3-yl)butan-2-one

(1-benzyloxycarbonylamino-ethyl)-phosphonic acid mono-[2-(1H-indol-3-yl)-1-phosphono-ethyl] ester

Refernces

• 1、 Jiménez-Moreno, Ester,G?mez, Ana M.,Bastida, Agatha,Corzana, Francisco,Jiménez-Oses, Gonzalo,Jiménez-Barbero, Jesús,Asensio, Juan Luis. "Modulating weak interactions for molecular recognition: A dynamic combinatorial analysis for assessing the contribution of electrostatics to the stability of CH-π bonds in water". . p. 4344 - 4348. Retrieved 2015.
• 2、 Koshiba,Yamauchi,Matsuyama,Miyakado,Sori,Sato. "Flavin-photosensitized production of indole-3-acetaldehyde from tryptophan". . p. 7603 - 7606. Retrieved 1993.
• 3、 Helmlinger, Juergen,Rausch, Thomas,Hilgenberg, Willy. "A Soluble Protein Factor from Chinese Cabbage Converts Indole-3-acetaldoxime to IAA". . p. 615 - 618. Retrieved 1987.
• 4、 Tan, Tong-De,Zhu, Xin-Qi,Jia, Mei,Lin, Yongjia,Cheng, Jun,Xia, Yuanzhi,Ye, Long-Wu. "Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides". supporting information. p. 1309 - 1312. Retrieved 2019/11/26.
• 5、 Guo, Zhenbo,Xu, Yiming,Peng, Yujie,Haroon ur Rashid,Quan, Wei,Xie, Peng,Wu, Lichuan,Jiang, Jun,Wang, Lisheng,Liu, Xu. "Design, synthesis and evaluation of novel (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit as anticancer agents". supporting information. p. 1133 - 1137. Retrieved 2019/03/06.