4-Amino-2-methylbenzonitrile

Base Information

• Chemical Name: 4-Amino-2-methylbenzonitrile
• CAS No.: 72115-06-1
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00429095
• Wikidata: Q82242004
• Mol file: 72115-06-1.mol

Synonyms:4-amino-2-methylbenzonitrile;72115-06-1;Benzonitrile, 4-amino-2-methyl-;4-Cyano-3-methylaniline;4-Amino-o-tolunitrile;SCHEMBL568981;4-amino-2-methyl benzonitrile;4-amino-2-methyl-benzonitrile;DTXSID00429095;RGHJWZADAWEIFE-UHFFFAOYSA-N;AB3033;MFCD09260793;AKOS006330303;AM83242;CS-W018776;4-amino-2-methylbenzonitrile, AldrichCPR;AS-20086;FT-0731430;EN300-367187;A866314;AE-562/43286977

Chemical Property of 4-Amino-2-methylbenzonitrile

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 90oC
• Boiling Point: 298.801 °C at 760 mmHg
• Flash Point: 134.511 °C
• PSA: 49.81000
• Density: 1.105 g/cm³
• LogP: 2.03008
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 132.068748264
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

99.90% ^*data from raw suppliers

4-Amino-2-methylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)N)C#N

Technology Process of 4-Amino-2-methylbenzonitrile

There total 9 articles about 4-Amino-2-methylbenzonitrile 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%

2-cyano-5-nitrotoluene (89001-53-6) → 4-amino-2-methylbenzonitrile (72115-06-1)

Guidance literature:

With tin(IV) chloride; In ethanol; for 3h; Heating / reflux;

Reference yield: 93.0%

N-(4-cyano-3-methylphenyl)-2-methylpropane-2-sulfinamide (1338209-70-3) → 4-amino-2-methylbenzonitrile (72115-06-1)

Guidance literature:

N-(4-cyano-3-methylphenyl)-2-methylpropane-2-sulfinamide; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,4-dioxane; water; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.075

Reference yield: 92.0%

potassium cyanide + amino-5-bromo-2-toluene (6933-10-4) → 4-amino-2-methylbenzonitrile (72115-06-1)

Guidance literature:

potassium cyanide; With acetic acid; In ethylene glycol; at 20 ℃; Sealed tube;

amino-5-bromo-2-toluene; With P(t-Bu)3 Palladacycle Gen_. 3; potassium acetate; In 1,4-dioxane; water; at 60 ℃; for 16h; Sealed tube;

DOI:10.1039/c7sc03912c

upstream raw materials:

2-cyano-5-nitrotoluene

hydrogenchloride

3-methyl-4-nitrobenzonitrile

N-(4-cyano-3-methylphenyl)-2-methylpropane-2-sulfinamide

Downstream raw materials:

4-amino-2-methylbenzoic acid

C₂₀H₂₁N₃O₃S

N-(4-cyano-3-methylphenyl)-2-(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl)acetamide

(2R)-3-bromo-N-(4-cyano-3-methylphenyl)-2-hydroxy-2-methylpropionamide

Refernces

• 1、 Kristensen, Steffan K.,Eikeland, Espen Z.,Taarning, Esben,Lindhardt, Anders T.,Skrydstrup, Troels. "Ex situ generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: Evidence for a transmetallation step between two oxidative addition Pd-complexes". . p. 8094 - 8105. Retrieved 2017/11/27.
• 2、 -. "Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use". Page/Page column 66. . Retrieved 2009/09/07.