1-(2-Cyanophenyl)piperazine

Base Information

• Chemical Name: 1-(2-Cyanophenyl)piperazine
• CAS No.: 111373-03-6
• Molecular Formula: C11H13N3
• Molecular Weight: 187.244
• Hs Code.: 2933599090
• European Community (EC) Number: 626-613-9
• UNII: LYK8UDP7Q4
• DSSTox Substance ID: DTXSID20370994
• Nikkaji Number: J837.493G
• Wikidata: Q72458914
• ChEMBL ID: CHEMBL275943
• Mol file: 111373-03-6.mol

Synonyms:1-(2-Cyanophenyl)piperazine;111373-03-6;2-(piperazin-1-yl)benzonitrile;2-piperazin-1-ylbenzonitrile;Benzonitrile, 2-(1-piperazinyl)-;2-Piperazinobenzonitrile;2-(1-piperazinyl)benzonitrile;2-(1-Piperazino)benzonitrile;2-Piperazin-1-yl-benzonitrile;2-piperazinylbenzenecarbonitrile;LYK8UDP7Q4;n-(2-cyanophenyl)piperazine;1-(2-Cyanophenyl)-piperazine;2-Piperazin-1-ylbenzenecarbonitrile;UNII-LYK8UDP7Q4;MFCD00040793;CHEMBL275943;D02YFZ;(2-cyano-phenyl)-piperazine;SCHEMBL233169;1-(2-cyanophenyl) piperazine;4-(2-cyano-phenyl)-piperazine;FRICBZWJFIRJOB-UHFFFAOYSA-;DTXSID20370994;FRICBZWJFIRJOB-UHFFFAOYSA-N;AMY23146;1-(2-Cyanophenyl)piperazine, 99%;BDBM50017458;STK503781;AKOS000261428;AC-2601;FS-1228;PD180699;SY002315;FT-0605532;P2448;EN300-62676;Z335292446;InChI=1/C11H13N3/c12-9-10-3-1-2-4-11(10)14-7-5-13-6-8-14/h1-4,13H,5-8H2

Chemical Property of 1-(2-Cyanophenyl)piperazine

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.19E-05mmHg at 25°C
• Melting Point: 113-115 °C
• Refractive Index: n20/D 1.5890(lit.)
• Boiling Point: 369.441 °C at 760 mmHg
• PKA: 8.77±0.10(Predicted)
• Flash Point: 177.232 °C
• PSA: 39.06000
• Density: 1.161 g/cm³
• LogP: 1.36168
• Sensitive.: Moisture Sensitive
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 187.110947427
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

97% ^*data from raw suppliers

1-(2-Cyanophenyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36
• Safety Statements: 16-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC=CC=C2C#N
• Uses: 1-(2-cyanophenyl)piperazine is used in the synthesis of melanocortin subtype-4 receptor (MC4R) agonists. MC4R is located in the hypothalamus and helps to regulate metabolism, feeding and reproductive behavior. Agonists to these receptors have shown to decrease feeding behaviors.

Technology Process of 1-(2-Cyanophenyl)piperazine

There total 9 articles about 1-(2-Cyanophenyl)piperazine 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%

piperazine (110-85-0) + 2-Chlorobenzonitrile (873-32-5) → 2-(piperazin-1-yl)benzonitrile (111373-03-6)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 0.166667h; Temperature;

DOI:10.1021/acs.orglett.6b02591

Reference yield: 87.0%

1-(2-iodobenzene)piperazine (1182838-13-6) + potassium hexacyanoferrate(II) trihydrate → 2-(piperazin-1-yl)benzonitrile (111373-03-6)

Guidance literature:

With tetrabutylammomium bromide; copper(II) acetate monohydrate; In water; at 20 - 140 ℃; Microwave irradiation;

DOI:10.1016/j.tetlet.2009.05.073

Reference yield: 86.0%

1-(2-bromophenyl)piperazine (1011-13-8) + potassium hexacyanoferrate(II) trihydrate → 2-(piperazin-1-yl)benzonitrile (111373-03-6)

Guidance literature:

With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium iodide; N,N`-dimethylethylenediamine; In water; at 20 - 140 ℃; Microwave irradiation;

DOI:10.1016/j.tetlet.2009.05.073

upstream raw materials:

N,N-bis(chloro-2-ethyl)amine

anthranilic acid nitrile

piperazine

2-Chlorobenzonitrile

Downstream raw materials:

ethyl 5-(3-(4-(2-cyanophenyl)piperazin-1-yl)propoxy)-1H-indole-2-carboxylate

2-{4-[4-((R)-1-hydroxymethyl-2-methylpropylamino)-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-2-yl]piperazin-1-yl}-benzonitrile

2-(4-(4-methoxyphenyl)piperazin-1-yl)benzonitrile

C₂₃H₂₃N₅O₂S

Refernces

• 1、 Reilly, Sean W.,Mach, Robert H.. "Pd-Catalyzed Synthesis of Piperazine Scaffolds under Aerobic and Solvent-Free Conditions". supporting information. p. 5272 - 5275. Retrieved 2016/10/31.
• 2、 -. "INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)". Paragraph 196-198. . Retrieved 2015/12/24.