2-(Dimethylamino)benzonitrile

Base Information

• Chemical Name: 2-(Dimethylamino)benzonitrile
• CAS No.: 20925-24-0
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• Hs Code.: 2926909090
• NSC Number: 204964
• DSSTox Substance ID: DTXSID20943187
• Nikkaji Number: J83.045C
• Wikidata: Q82920233
• Mol file: 20925-24-0.mol

Synonyms:2-(dimethylamino)benzonitrile;20925-24-0;Benzonitrile, (dimethylamino)-;2-Dimethylamino-benzonitrile;MFCD01313389;NSC204964;dimethylaminobenzonitrile;N,N-Dimethylanthranilonitrile;SCHEMBL148781;DTXSID20943187;Benzonitrile, 2-(dimethylamino)-;AKOS000261887;NSC-204964;PS-5826;SB75447;SY021589;BB 0258792;CS-0134628;EN300-82597;A879346;Z335294592

Chemical Property of 2-(Dimethylamino)benzonitrile

Chemical Property:

• Vapor Pressure: 0.0153mmHg at 25°C
• Melting Point: 130 °C
• Refractive Index: 1.55
• Boiling Point: 256.6 °C at 760 mmHg
• Flash Point: 105.5 °C
• PSA: 27.03000
• Density: 1.04 g/cm³
• LogP: 1.62428
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 166

Purity/Quality:

98% ^*data from raw suppliers

2-(Dimethylamino)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=CC=C1C#N

Technology Process of 2-(Dimethylamino)benzonitrile

There total 8 articles about 2-(Dimethylamino)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: 94.0%

anthranilic acid nitrile (1885-29-6) + methyl iodide (74-88-4) → 2-N,N-dimethylaminobezonitrile (20925-24-0)

Guidance literature:

anthranilic acid nitrile; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1.25h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201708578

Reference yield: 92.0%

methanol (67-56-1) + o-nitrobenzonitrile (612-24-8) → 2-N,N-dimethylaminobezonitrile (20925-24-0)

Guidance literature:

With aluminum (III) chloride; water; In acetonitrile; at 20 ℃; Irradiation;

DOI:10.1002/cssc.202002459

Reference yield: 85.0%

2-bromo-N,N-dimethylaniline (698-00-0) + sodium cyanide (143-33-9,25596-52-5) → 2-N,N-dimethylaminobezonitrile (20925-24-0)

Guidance literature:

With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine; In toluene; at 130 ℃; for 24h;

DOI:10.1021/ja0299708

upstream raw materials:

N,N,N,N,N,N-hexamethylphosphoric triamide

2-Chlorobenzonitrile

P-toluenesulfonyl cyanide

N,N-dimethyl-aniline

Downstream raw materials:

3-Cyano-4-dimethylamino-benzaldehyd

1‐methyl‐3‐phenyl‐1H‐indazole

N,N-dimethyl-2-[imino(phenyl)methyl]aniline

2-(aminomethyl)phenyl-N,N-dimethylamine

Refernces

• 1、 Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori. "Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)?H Addition to Carbon–Carbon Double Bonds". supporting information. p. 14272 - 14276. Retrieved 2017/10/23.
• 2、 Hatsuda, Masanori,Seki, Masahiko. "A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C". . p. 1849 - 1853. Retrieved 2007/10/03.