4-(Dimethylamino)benzonitrile

Base Information

• Chemical Name: 4-(Dimethylamino)benzonitrile
• CAS No.: 1197-19-9
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• Hs Code.: 29269090
• European Community (EC) Number: 214-819-8
• NSC Number: 409122
• UNII: 8391XON0MF
• DSSTox Substance ID: DTXSID4073255
• Nikkaji Number: J80.082A
• Wikidata: Q27269416
• Mol file: 1197-19-9.mol

Synonyms:4-cyano-N,N-dimethylaniline;4-cyanodimethylaniline;para-cyano-N,N-dimethylaniline

Chemical Property of 4-(Dimethylamino)benzonitrile

Chemical Property:

• Appearance/Colour: light brown crystalline powder
• Vapor Pressure: 0.000353mmHg at 25°C
• Melting Point: 72-75 °C
• Refractive Index: 1.55
• Boiling Point: 318.8 °C at 760 mmHg
• PKA: 1.61±0.12(Predicted)
• Flash Point: 145.4 °C
• PSA: 27.03000
• Density: 1.04 g/cm³
• LogP: 1.62428
• Solubility.: soluble in Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

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

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

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C#N
• Uses: 4-(Dimethylamino)benzonitrile is used in predicting the carcinogenicity of aromatic amine derivative in UK EMS collaborative study. 4-(Dimethylamino)benzonitrile can be used in the synthesis of 3,6-diphenyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione derivatives.

Technology Process of 4-(Dimethylamino)benzonitrile

There total 133 articles about 4-(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: 100.0%

phenylethane 1,2-diol (93-56-1) + 4-cyano-N,N-dimethylaniline-N-oxide (62820-00-2) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-cyano-N-methylaniline (4714-62-9) + benzaldehyde (100-52-7) + 4-cyano-N,N-dimethylaniline (1197-19-9)

Guidance literature:

With chloro(5,10,15,20-tetraphenylporphyrinato)chromium(III); In acetonitrile; for 0.666667h; Rate constant; Ambient temperature; Irradiation; oxygen transfer was investigated, different irradiation time;

DOI:10.1021/ja00312a083

Reference yield: 96.0%

2,3-Dimethyl-2-butene (563-79-1) + 4-cyano-N,N-dimethylaniline-N-oxide (62820-00-2) → 2,3-dimethyl-2,3-epoxybutane (5076-20-0) + N-(4-cyanophenyl)-N-methylformamide (97860-68-9) + 4-cyano-N-methylaniline (4714-62-9) + N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine (79121-26-9) + 6-cyano-3,4-norbornyl-N-methyl-1,2,3,4-tetrahydroquinoline (110190-07-3) + 4-cyano-N,N-dimethylaniline (1197-19-9)

Guidance literature:

(TPPC₂cap)Fe^IIISbF₆; In dichloromethane; at 25 ℃; Product distribution; Rate constant; various concentrations of the catalysts, time, and alkene;

DOI:10.1021/ja00245a040

Reference yield: 84.0%

4-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-3,6,6-trimethyl-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester (117227-36-8) → 4-dimethylamino-benzaldehyde (100-10-7) + 4-cyano-N,N-dimethylaniline (1197-19-9)

Guidance literature:

With sodium methylate; In ethanol; for 3h; Product distribution; Heating;

upstream raw materials:

pyridine

benzoyl chloride

(E)-4-dimethylaminobenzaldehyde oxime

4-dimethylamino-benzaldehyde-[O-(2,4-dinitro-phenyl)-oxime ]

Downstream raw materials:

4-(Dimethylamino)benzophenone

3-amino-3-(4-dimethylamino-phenyl)-acrylonitrile

(4-cyanophenyl)trimethylammonium iodide

4'-dimethylaminoacetophenone

Refernces

• 1、 Wong, Wah-Hun,Ostovic, Drazen,Bruice, Thomas C.. "Kinetics and Mechanism of Oxygen Transfer in the Reaction of p-Cyano-N,N-dimethylaniline N-Oxide with Metalloporphyrin Salts. 5. The Influence of Imidazole Ligation of (meso-Tetrakis(2,6-dimethylphenyl)porphinato)manganese(III) Chloride on the Rates of Oxygen Transfer from N-Oxide to...". . p. 3428 - 3436. Retrieved 1987.
• 2、 Richardson, Jeffery,Mutton, Simon P.. "Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues". . p. 4922 - 4931. Retrieved 2018.
• 3、 Blatter,Lukaszewski,Stevens. "-". . . Retrieved 1963.
• 4、 Ghosh, Pranab,Subba, Raju. "FeCl3 mediated one-pot route to nitriles". . p. 4885 - 4887. Retrieved 2013.
• 5、 Diaz, Daniel E.,Bhadra, Mayukh,Karlin, Kenneth D.. "Dimethylanilinic N-Oxides and Their Oxygen Surrogacy Role in the Formation of a Putative High-Valent Copper-Oxygen Species". . p. 13746 - 13750. Retrieved 2019.
• 6、 Gucma, Miroslaw,Golebiewski, W. Marek. "Convenient conversion of aldoximes into nitriles with N-chlorosuccinimide and pyridine". . p. 1997 - 1999. Retrieved 2008.
• 7、 Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi. "Nitrile Synthesis via Desulfonylative-Smiles Rearrangement". . p. 4460 - 4467. Retrieved 2022/03/15.
• 8、 -. "Efficient nitriding reagent and application thereof". Paragraph 0219-0222. . Retrieved 2021/03/31.