3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile

Base Information

• Chemical Name: 3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile
• CAS No.: 179055-95-9
• Molecular Formula: C11H9N3
• Molecular Weight: 183.21
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID00441010
• Wikidata: Q82257542
• Mol file: 179055-95-9.mol

Synonyms:3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile;179055-95-9;3-(2-methylpyrazol-3-yl)benzonitrile;Benzonitrile, 3-(1-methyl-1H-pyrazol-5-yl)-;Benzonitrile,3-(1-methyl-1H-pyrazol-5-yl)-;SCHEMBL8807138;DTXSID00441010;MFCD09702401;AKOS006344501;MS-22087;CS-0336767;FT-0752033;A1-41290

Chemical Property of 3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 96 °C
• Refractive Index: 1.61
• Boiling Point: 349.935 °C at 760 mmHg
• Flash Point: 165.435 °C
• PSA: 41.61000
• Density: 1.11 g/cm³
• LogP: 1.95878
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 183.079647300
• Heavy Atom Count: 14
• Complexity: 242

Purity/Quality:

98% ^*data from raw suppliers

3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Harmful:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC=N1)C2=CC=CC(=C2)C#N

Technology Process of 3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile

There total 4 articles about 3-(1-Methyl-1H-pyrazol-5-yl)benzonitrile 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: 61.0%

1-methyl-1H-pyrazole (930-36-9) + 3-cyanobromobenzene (6952-59-6) → 3-(1-methylpyrazol-4-yl)benzonitrile (179055-94-8) + 3-(1-methylpyrazol-5-yl)benzonitrile (179055-95-9)

Guidance literature:

With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1260076

Reference yield: 29.0%

(E)-3-(3-(dimethylamino)acryloyl)benzonitrile (179055-13-1) + methylhydrazine (60-34-4) → 3-(1-methyl-1H-pyrazol-3-yl)benzonitrile (207909-05-5) + 3-(1-methylpyrazol-5-yl)benzonitrile (179055-95-9)

Guidance literature:

With acetic acid; for 3.5h; Ambient temperature;

DOI:10.1021/jm9800853

Reference yield:

1-methyl-1H-pyrazole (930-36-9) + 3-cyanobromobenzene (6952-59-6) → 3-(1-methylpyrazol-4-yl)benzonitrile (179055-94-8) + 3-(2-methylpyrazol-3-yl)benzonitrile (1570098-47-3) + 3-(1-methylpyrazol-5-yl)benzonitrile (179055-95-9)

Guidance literature:

With PdCl(1,4-bis(diphenylphosphino)butane)(C₃H₅); potassium acetate; In N,N-dimethyl-formamide; at 150 ℃; for 72h; Overall yield = 44 %; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.01.079

upstream raw materials:

(E)-3-(3-(dimethylamino)acryloyl)benzonitrile

methylhydrazine

3-acethylbenzonitrile

1-methyl-1H-pyrazole

Downstream raw materials:

Cycloheptyl-[3-(2-methyl-2H-pyrazol-3-yl)-benzyl]-amine

Benzyl-[3-(2-methyl-2H-pyrazol-3-yl)-benzyl]-amine

3-(1-methylpyrazol-5-yl)benzaldehyde

Refernces

• 1、 Beladhria, Anissa,Beydoun, Kassem,Ammar, Hamed Ben,Salem, Ridha Ben,Doucet, Henri. "Pd-catalysed direct 5-arylation of 1-methylpyrazole with aryl bromides". experimental part. p. 2553 - 2560. Retrieved 2011/10/04.