74896-24-5

Basic information

• Product Name: 4-AMINO-3,5-DIMETHYL-BENZONITRILE
• Synonyms: 4-AMINO-3,5-DIMETHYL-BENZONITRILE;4-Amino-3,5-dimethylbenzo...;NSC 128902
• CAS NO: 74896-24-5
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.19
• Mol File: 74896-24-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 106.0-107.5 °C
• Boiling Point: 322.2 °C at 760 mmHg
• Flash Point: 148.7 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 0.000283mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.43±0.10(Predicted)
• CAS DataBase Reference: 4-AMINO-3,5-DIMETHYL-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3,5-DIMETHYL-BENZONITRILE(74896-24-5)
• EPA Substance Registry System: 4-AMINO-3,5-DIMETHYL-BENZONITRILE(74896-24-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• Hazardous Substances Data: 74896-24-5(Hazardous Substances Data)

Usage

General Description

4-Amino-3,5-dimethyl-benzonitrile is a chemical compound with the molecular formula C9H10N2. It is a white to light yellow solid that is used in the synthesis of various pharmaceuticals and organic compounds. 4-AMINO-3,5-DIMETHYL-BENZONITRILE is a derivative of benzonitrile and contains an amino group and two methyl groups attached to the benzene ring. It has potential applications in the pharmaceutical industry, particularly in the development of new drugs and medications. Additionally, 4-Amino-3,5-dimethyl-benzonitrile may also be used in research and laboratory settings for its unique chemical properties and reactivity.

InChI:InChI=1/C9H10N2/c1-6-3-8(5-10)4-7(2)9(6)11/h3-4H,11H2,1-2H3

Upstream product

• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 544-92-3 copper(I) cyanide 
• 1616514-67-0 tert-butyl 2-(4-cyano-2,6-dimethylphenyl)-1-(4-methylphenyl)hydrazinecarboxylate 
• 1639128-67-8 N'-Boc-N-(4-cyano-2,6-dimethylphenyl)hydrazine 
• 110-70-3 N,N`-dimethylethylenediamine 
• 87-62-7 2,6-dimethylaniline 
• 24596-18-7 4-chloro-2,6-dimethylaniline 

Downstream Products

• 917388-67-1 4-amino-3,5-dimethylbenzylamine 
• 1097629-24-7 4-chloro-3,5-dimethyl-benzonitrile 
• 4198-90-7 3,5-dimethyl-4-hydroxybenzonitrile 
• 1414864-89-3 4-((4,4-dimethyl-1-phenylpent-2-en-1-yl)oxy)-3,5-dimethylbenzonitrile 
• 1616514-81-8 4-[(2-amino-5-methylphenyl)amino]-3,5-dimethylbenzonitrile 
• 1639128-71-4 3,5-dimethyl-4-(p-tolyldiazenyl)benzonitrile 
• 1639128-67-8 N'-Boc-N-(4-cyano-2,6-dimethylphenyl)hydrazine 
• 1616514-67-0 tert-butyl 2-(4-cyano-2,6-dimethylphenyl)-1-(4-methylphenyl)hydrazinecarboxylate 
• 1609687-07-1 4-[6-(4-cyanophenylamino)pyridin-2-yl]amino-3,5-dimethylbenzonitrile 
• 1609686-80-7 4-{6-[(4-fluorophenyl)amino]-5-fluoropyridin-2-ylamino}-3,5-dimethylbenzonitrile 

Relevant articles and documents

Unusual Sensitivity to the Concentration of Ethanol in the Boron Trifluoride/Ethanol-Catalyzed Synthesis of 5,10,15,20-Tetrakis(4-cyano-2,6-dimethylphenyl)porphyrin by the Lindsey Method

The boron trifluoride/ethanol-catalyzed condensation of 4-cyano-2,6-dimethylbenzaldehyde 1b with pyrrole by the Lindsey method to give the new, ortho-disubstituted 5,10,15,20-tetrakis(4-cyano-2,6dimethylphenyl)porphyrin 2 was found to be highly sensitive

Regioselectivity of the ortho- and para-semidine, and diphenyline rearrangements

The regioselectivity of the o-semidine, p-semidine, and diphenyline rearrangements of unsymmetrical N,N′-diarylhydrazines was studied experimentally. The results indicate that their electron-rich nitrogen atom is first protonated and then the electron-poor non-protonated nitrogen atom undergoes an N[1,3]-sigmatropic shift to the ortho-position of the electron-rich aryl rings, generating key intermediates. The intermediates can undergo (1) a direct proton transfer to give o-semidines, (2) a second N[1,3]-shift of the electron-poor nitrogen atom and then proton transfer to furnish p-semidines, and (3) a [3,3]-sigmatropic shift and subsequent proton transfer to yield diphenylines. It is the first N[1,3]-sigmatropic shift step that plays an important role in controlling the regioselectivity in the three rearrangements, further determining the structures of o-semidines, p-semidines, and diphenylines. The current results provide new insights into the o/p-semidine and diphenyline rearrangements and useful information for controlling and predicting the structures of the rearrangement products.

N[1,3]-sigmatropic shift in the benzidine rearrangement: Experimental and theoretical investigation

The N[1,3]-sigmatropic shift in the benzidine rearrangement has been studied in depth experimentally with the aid of density functional theory (DFT) calculations. The designed substituted N,N′-diaryl hydrazines rearrange exclusively to the expected o/p-semidines and diphenylines. Intercrossing experiments support the intramolecular rearrangement process. Radical trapping experiments exclude the intermediacy of biradicals in the rearrangements. Computational results demonstrate that the o-semidine rearrangement involves a novel N[1,3]-sigmatropic shift and the p-semidine rearrangement proceeds via tandem N[1,3]/N[1,3]-sigmatropic shifts, while the diphenyline rearrangement occurs through cascade N[1,3]/[3,3]-sigmatropic shifts. The proposed mechanism involving the key N[1,3]-sigmatropic shift as the rate-limiting step is in good agreement with reported kinetic isotope measurements. The combined methods provide new insight into the formation mechanism of o/p-semidines and diphenylines in the benzidine rearrangement and support the unprecedented suprafacial symmetry allowed N[1,3]-sigmatropic shift with an inversion of the configuration in the migrating nitrogen atom. This journal is the Partner Organisations 2014.