3-(2-Methyl-1h-indol-3-yl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-(2-Methyl-1h-indol-3-yl)-3-oxopropanenitrile
• CAS No.: 76397-72-3
• Molecular Formula: C12H10N2O
• Molecular Weight: 198.224
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID40351624
• Nikkaji Number: J2.150.776H
• Wikidata: Q72492078
• ChEMBL ID: CHEMBL1773459
• Mol file: 76397-72-3.mol

Synonyms:3-(2-methyl-1h-indol-3-yl)-3-oxopropanenitrile;76397-72-3;3-(CYANOACETYL)-2-METHYLINDOLE;D(+)-glucuronicacid;Enamine_003846;Oprea1_351568;3-(2-Methyl-1H-indol-3-yl)-3-oxo-propionitrile;SCHEMBL138148;2-methyl-3-cyanoacetyl indole;CHEMBL1773459;DTXSID40351624;HMS1404O18;BDA39772;MFCD02330570;AKOS000115173;AC-0832;IDI1_007489;CS-0218588;FT-0677590;EN300-01440;J-510536;Z56846729

Chemical Property of 3-(2-Methyl-1h-indol-3-yl)-3-oxopropanenitrile

Chemical Property:

• Vapor Pressure: 3.93E-08mmHg at 25°C
• Melting Point: 184 °C
• Refractive Index: 1.646
• Boiling Point: 445.5 °C at 760 mmHg
• PKA: 8.63±0.30(Predicted)
• Flash Point: 223.2 °C
• PSA: 56.65000
• Density: 1.242 g/cm³
• LogP: 2.57268
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.079312947
• Heavy Atom Count: 15
• Complexity: 304

Purity/Quality:

98%min ^*data from raw suppliers

3-(2-methyl-1H-indol-3-yl)-3-oxopropanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1)C(=O)CC#N

Technology Process of 3-(2-Methyl-1h-indol-3-yl)-3-oxopropanenitrile

There total 3 articles about 3-(2-Methyl-1h-indol-3-yl)-3-oxopropanenitrile 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: 92.0%

2-methyl-1H-indole (95-20-5) + cyanoacetic acid (372-09-8) → 3-(2-methyl-1H-indol-3-yl)-3-oxopropanenitrile (76397-72-3)

Guidance literature:

With acetic anhydride; at 85 ℃; for 0.166667h;

DOI:10.1016/j.ejmech.2021.113215

Reference yield: 81.0%

2-methyl-1H-indole (95-20-5) + potassium 2-cyanoacetate (7062-95-5) → 3-(2-methyl-1H-indol-3-yl)-3-oxopropanenitrile (76397-72-3)

Guidance literature:

With methanesulfonyl chloride; In acetonitrile; for 1h; Ambient temperature;

Reference yield:

2-chloro-1-(2-methyl-1H-indol-3-yl)ethan-1-one (38693-08-2) + potassium cyanide (151-50-8) → 3-(2-methyl-1H-indol-3-yl)-3-oxopropanenitrile (76397-72-3)

Guidance literature:

With ethanol;

upstream raw materials:

2-chloro-1-(2-methyl-1H-indol-3-yl)ethan-1-one

potassium cyanide

2-methyl-1H-indole

potassium 2-cyanoacetate

Downstream raw materials:

4-(4-chlorophenyl)-3-methyl-6-(2-methyl-1H-indol-3-yl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

2-[3,5-diphenyl-1,3,4-thiadiazol-2(3H)-ylidene]-3-(2-methyl-1H-indol-3-yl)-3-oxopropionitrile

3-(2-methyl-1H-indol-3-yl)-2-[3-(4-nitrophenyl)-5-(thiophen-2-yl)-1,3,4-thiadiazol-2(3H)-ylidene]-3-oxopropionitrile

ethyl 5-[1-cyano-2-(2-methyl-1H-indol-3-yl)-2-oxoethylidene]-4-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate

Refernces

• 1、 Kalhor, Sima,Zarei, Mahmoud,Sepehrmansourie, Hassan,Zolfigol, Mohammad Ali,Shi, Hu,Wang, Jinping,Arjomandi, Jalal,Hasani, Masoumeh,Schirhagl, Romana. "Novel uric acid-based nano organocatalyst with phosphorous acid tags: Application for synthesis of new biologically-interest pyridines with indole moieties via a cooperative vinylogous anomeric based oxidation". . . Retrieved 2021/04/23.
• 2、 Adepu, Raju,Dhanaji, Jadhav Rahul,Samatha, Polasani,Mainkar, Prathama S.,Chandrasekhar, Srivari. "Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence". supporting information. p. 8224 - 8228. Retrieved 2020/11/18.