4,5,6,7-Tetrahydro-1H-indole

Base Information

• Chemical Name: 4,5,6,7-Tetrahydro-1H-indole
• CAS No.: 13618-91-2
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2933990090
• European Community (EC) Number: 919-829-2,624-521-3
• NSC Number: 122455
• DSSTox Substance ID: DTXSID80159727
• Nikkaji Number: J407.033J
• Wikidata: Q27461810
• Mol file: 13618-91-2.mol

Synonyms:4,5,6,7-Tetrahydro-1H-indole;13618-91-2;4,5,6,7-Tetrahydroindole;1H-Indole, 4,5,6,7-tetrahydro-;2,3-Tetramethylenepyrrole;MFCD00012134;NSC122455;NSC 122455;SCHEMBL13511;DTXSID80159727;1H-Indole,4,5,6,7-tetrahydro-;4,5,6,7-Tetrahydroindole, 98%;AKOS006220512;Benzaldehyde,4-amino-3-methoxy-(9Cl);NSC-122455;AS-50369;SY017713;BB 0260885;CS-0006599;FT-0600350;EN300-109738;P10023;J-006819;Q27461810;Z274765016;JZ9

Chemical Property of 4,5,6,7-Tetrahydro-1H-indole

Chemical Property:

• Vapor Pressure: 0.0293mmHg at 25°C
• Melting Point: 53-57 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 253.3 °C at 760 mmHg
• Flash Point: 101.4 °C
• PSA: 15.79000
• Density: 1.057g/cm³
• LogP: 1.89350
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5,6,7-Tetrahydro-1H-indole ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC2=C(C1)C=CN2
• Uses: 4,5,6,7-Tetrahydro-1H-indole is used in preparation of chiral tetraaryl-substituted Methane. Also, used in preparation of 4-substituted Phenylamidine derivatives used for controlling phytopathogenic microorganisms. 4,5,6,7-Tetrahydroindole was used as reactant in:synthesis of ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)-2-propynoatepreparation of BODIPY dyesN-alkylation with chloromethyloxiranepreparation of hydroindolepropynoate by chemo- and regioselective solvent-free ethynylationpalladium- and copper-free cross-coupling of halopropynoatespreparation of carbonylalkenyl indoles via coupling with dicarbonyl compounds1:2 annelation of 4,5,6,7-tetrahydroindole with 1-benzoyl-2-phenylacetylene

Technology Process of 4,5,6,7-Tetrahydro-1H-indole

There total 43 articles about 4,5,6,7-Tetrahydro-1H-indole 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: 90.0%

indole (120-72-9) → 4,5,6,7-tetrahydroindole (13618-91-2) + 1-indoline (496-15-1)

Guidance literature:

With 5% Ru/MgO; hydrogen; In tetrahydrofuran; at 150 ℃; for 0.4h; under 38002.6 Torr;

DOI:10.1016/j.jcat.2013.12.017

Reference yield: 88.0%

1,4,5,6-tetrahydro-7H-indol-7-one (23456-78-2) → 4,5,6,7-tetrahydroindole (13618-91-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1016/0040-4020(96)00046-4

Reference yield: 84.0%

1,5,6,7-tetrahydro-indol-4-one (13754-86-4) → 4,5,6,7-tetrahydroindole (13618-91-2)

Guidance literature:

1,5,6,7-tetrahydro-indol-4-one; With lithium aluminium tetrahydride; In tetrahydrofuran; at 75 - 80 ℃; for 26.5h; Reflux; Inert atmosphere;

With water; sodium hydroxide; In ethyl acetate; for 0.5h;

upstream raw materials:

4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid

cyclohexanone-oxime

Vinyl bromide

1,5,6,7-tetrahydro-indol-4-one

Downstream raw materials:

4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

1-isopropenyl-4,5,6,7-tetrahydro-1H-indole

4-fluoro-2-(6-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenylamino)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-2-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Refernces

• 1、 McComas, Casey C.,Van Vranken, David L.. "Reduction of the indole ring system: Synthesis of 4,5,6,7-tetrahydroindoles". . p. 8039 - 8043. Retrieved 1999.
• 2、 Trofimov,Mikhaleva,Shmidt,Vasil'Tsov,Ivanov,Protsuk,Ryapolov. "A new technology for the synthesis of 4,5,6,7-tetrahydroindole". . p. 307 - 310. Retrieved 2010.
• 3、 Zav'yalov,Skoblik. "-". . . Retrieved 1977.
• 4、 Remers et al.. "-". . p. 279. Retrieved 1971.
• 5、 -. "STABILIZATION OF ACTIVE METAL CATALYSTS AT METAL-ORGANIC FRAMEWORK NODES FOR HIGHLY EFFICIENT ORGANIC TRANSFORMATIONS". Paragraph 0349. . Retrieved 2019/01/07.
• 6、 Klein, Andreas Sebastian,Brass, Hannah Ursula Clara,Klebl, David Paul,Classen, Thomas,Loeschcke, Anita,Drepper, Thomas,Sievers, Sonja,Jaeger, Karl-Erich,Pietruszka, J?rg. "Preparation of cyclic prodiginines by mutasynthesis in pseudomonas putida kt2440". . p. 1545 - 1552. Retrieved 2018/10/21.