5637-42-3

Basic information

• Product Name: N-(4-Cyanophenyl)guanidine
• Synonyms: N-(4-Cyanophenyl)guanidine;4-Guanidinobenzonitrile;1-(4-cyanophenyl)guanidine;4-Cyanophenyl Guanidine
• CAS NO: 5637-42-3
• Molecular Formula: C₈H₈N₄
• Molecular Weight: 160.18
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Intermediate of Etravirine
• Mol File: 5637-42-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 155-162°C
• Boiling Point: 316.6 °C at 760 mmHg
• Flash Point: 145.3 °C
• Appearance: White solid
• Density: 1.25 g/cm³
• Vapor Pressure: 0.000406mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO, Methanol
• PKA: 9.91±0.10(Predicted)
• CAS DataBase Reference: N-(4-Cyanophenyl)guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Cyanophenyl)guanidine(5637-42-3)
• EPA Substance Registry System: N-(4-Cyanophenyl)guanidine(5637-42-3)

Safety Data

• Hazardous Substances Data: 5637-42-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

An intermediate in the preparation of Etravirine

InChI:InChI=1/C8H8N4/c9-5-6-1-3-7(4-2-6)12-8(10)11/h1-4H,(H4,10,11,12)

Upstream product

• 3460-55-7 4-cyanophenylthiourea 
• 420-04-2 CYANAMID 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 1212390-27-6 4-{4-[3-(4-benzyloxyphenoxy)phenyl]-6-methylpyrimidin-2-ylamino}benzo-1-nitrile 
• 189956-45-4 4-[(4-hydroxy-2-pyrimidinyl)amino]benzonitrile 
• 244768-32-9 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile 
• 1398507-09-9 4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile 
• 269055-75-6 4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile 
• 1404118-68-8 N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]-benzamide 
• 1404118-67-7 N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]-benzamide 
• 1404118-66-6 N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide 
• 1398507-08-8 4-((4-amino-6-chloropyrimidin-2-yl)amino)benzonitrile 
• 1398507-07-7 4-(4-amino-6-hydroxy-pyrimidin-2-ylamino)-benzonitrile 
• 1383716-96-8 4-(4-(2-(methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)pyrimidin-2-ylamino)benzonitrile 
• 1070377-34-2 4-[[6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile 
• 329187-59-9 4-(4,6-dichloropyrimidine-2-yl-amino)benzonitrile 
• 269055-15-4 etravirine 

Relevant articles and documents

Iron-promoted sulfur sequestration for the substituent-dependent regioselective synthesis of tetrazoles and guanidines

We have established a facile and versatile synthetic methodology for the construction of tetrazoles and guanidines in the presence of an eco-friendly, inexpensive, easily available iron reagent. Aromatic thioureas with electron-donating substituents produced their respective target products in quantitative yield. In contrast, when electron-withdrawing substituted aromatic thioureas were used, the expected products were obtained in reduced yield. However, the desired products were obtained in good yield at moderate temperature. In addition, mechanistic studies revealed that the synthetic route involved iron-based subsequent reactions of addition and removal of sulfur.

PROCESS FOR ETRAVIRINE INTERMEDIATE AND POLYMORPHS OF ETRAVIRINE

4-[[6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile is a key intermediate for the preparation of etravirine. The present invention provides a process for preparation of 4-[[6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile. The present invention also provides a novel process for the preparation of etravirine crystalline form I. The present invention further provides novel crystalline forms of etravirine, processes for their preparation and pharmaceutical compositions comprising them.

Synthesis of aryl phosphates based on pyrimidine and triazine scaffolds

The syntheses of the triazinyl-based bis-aryl phosphates 2 and 3, and of the aminopyrimidyl-based aryl phosphate 4 are described. Each compound contains a diaryl ether-phosphate structural motif. The synthetic route to bis-aryl phosphates 2 and 3 consisted in two nucleophilic substitution reactions with amines from cyanuric chloride, followed by a Suzuki coupling with the resulting 2,4-diamino-6-chloro-1,3,5-triazine derivative 12 to introduce the diaryl ether functionality. Aryl phosphate 4 was obtained via condensation of aryl guanidine 34 with aryloxyphenyl butenone 31. These de novo-designed aryl phosphates were evaluated as potential inhibitors of the Grb2-SH2 domain using an ELISA assay. The water-soluble sodium salt 26 of 3 gave an IC50 value in the high micromolar range. Molecular modeling studies were subsequently performed upon modifying the 1,3,5-trisubstituted triazine scaffold of 3. Non-phosphate derivatives encompassing cyclopropane, pyrrole, keto-acid, and IZD fragments were thus step-wise designed and their Grb2-SH2 complexes were modeled by molecular dynamics. Some derivatives gave rise to an enriched pattern of H-bonds and cation-π interactions with Grb2-SH2.