1-Acetylindole

Base Information

• Chemical Name: 1-Acetylindole
• CAS No.: 576-15-8
• Molecular Formula: C10H9 N O
• Molecular Weight: 159.188
• Hs Code.: 29339990
• European Community (EC) Number: 209-396-1
• NSC Number: 521758
• DSSTox Substance ID: DTXSID9060362
• Nikkaji Number: J6.563C
• Wikidata: Q63395317
• Mol file: 576-15-8.mol

Synonyms:1-Acetylindole;576-15-8;1-(1H-indol-1-yl)ethanone;N-Acetylindole;1-indol-1-ylethanone;1-Acetyl-1H-indole;1H-Indole, 1-acetyl-;Indole, 1-acetyl-;Ethanone, 1-(1H-indol-1-yl)-;EINECS 209-396-1;NSC 521758;1-(1H-indol-1-yl)ethan-1-one;N-acetyl indole;NSC521758;1-Acetylindole, 98%;ChemDiv2_000105;SCHEMBL41252;1-(1H-indol-1-yl)-ethanone;DTXSID9060362;CHEBI:177032;HMS1369E17;MFCD00038005;AKOS009158602;NSC-521758;AS-37920;CS-0155049;EU-0000214;FT-0629822;A831524;SR-01000389828;SR-01000389828-1;Q63395317;RRI

Chemical Property of 1-Acetylindole

Chemical Property:

• Appearance/Colour: clear to light yellow liquid.
• Vapor Pressure: 0.0111mmHg at 25°C
• Melting Point: 189 °C
• Refractive Index: n20/D 1.607(lit.)
• Boiling Point: 123-125 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 22.00000
• Density: 1.387 g/mL at 25 °C(lit.)
• LogP: 2.30140
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

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

1-Acetylindole 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)N1C=CC2=CC=CC=C21
• Uses: 1-Acetylindole may be used in the stereocontrolled synthesis of (±)-geissoschizine. It may be used in the preparation of (1-acetyl-κO-indolyl-κC2)tetracarbonylmanganese, via a standard cyclomanganation procedure.

Technology Process of 1-Acetylindole

There total 59 articles about 1-Acetylindole 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%

indole (120-72-9) + acetyl chloride (75-36-5) → N-acetylindole (576-15-8)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate;

DOI:10.1080/00397919908085950

Reference yield: 99.0%

1-Acetyl-2,3-dihydro-1H-indole (16078-30-1) → N-acetylindole (576-15-8)

Guidance literature:

With H₈O₂₀P₈Pt₂^(4-)*4C₃₄H₇₂N⁽¹⁺⁾; In methanol; Inert atmosphere; Irradiation;

DOI:10.1039/c8sc05600e

Reference yield: 98.0%

indole (120-72-9) + acetic anhydride (108-24-7) → N-acetylindole (576-15-8)

Guidance literature:

With dmap; triethylamine; In 1,2-dichloro-ethane; at 20 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201904413

upstream raw materials:

indole

acetic anhydride

N-acetylindolin-3-ol

ethyl acetate

Downstream raw materials:

3-acetylindole

1-(1H-indol-6-yl)ethan-1-one

1-acetyl-2-(2,5-dimethylphenyl)indole

1,3-diacetyl-1H-indole

Refernces

• 1、 Larock, R.C.,Liu, C.-L.,Lau, H. H.,Varaprath, S.. "HETEROCYCLIC SYNTHESIS VIA THALLATION AND SUBSEQUENT PALLADIUM-PROMOTED OLEFINATION". . p. 4459 - 4462. Retrieved 1984.
• 2、 Tayu, Masanori,Watanabe, Ryuta,Isogi, Satoshi,Saito, Nozomi. "A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from N-Arylynamides". supporting information. p. 1147 - 1151. Retrieved 2021/01/04.
• 3、 Chen, Shanping,Deng, Guo-Jun,Jiang, Pingyu,Ni, Penghui,Tuo, Xiaolong,Wang, Xiaodong. "Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines". . p. 8348 - 8351. Retrieved 2020/03/11.