2002-16-6

Basic information

• Product Name: 1-phenylguanidine
• Synonyms: 1-phenylguanidine;Phenylguanidine;phenyl guanidine phenyl guanidine;N-Phenylguanidine
• CAS NO: 2002-16-6
• Molecular Formula: C₇H₉N₃
• Molecular Weight: 135.16646
• EINECS: 217-898-7
• Mol File: 2002-16-6.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 290.5°Cat760mmHg
• Flash Point: 129.5°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.00207mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: pK1:10.77(+1) (25°C)
• CAS DataBase Reference: 1-phenylguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylguanidine(2002-16-6)
• EPA Substance Registry System: 1-phenylguanidine(2002-16-6)

Safety Data

• Hazardous Substances Data: 2002-16-6(Hazardous Substances Data)

Usage

Uses

Phenylguanidine is used to prepare (4-Aminomethyl)phenylguanidine derivative, which is a nonpeptidic highly selective inhibitor of human urokinase. A series of substituted phenylguanidine compounds are selective inhibitors of urokinase.

InChI:InChI=1/C7H9N3.ClH/c8-7(9)10-6-4-2-1-3-5-6;/h1-5H,(H4,8,9,10);1H

Upstream product

• 674-81-7 nitrosoguanidine 
• 142-04-1 aniline hydrochloride 
• 556-88-7 nitroguanidine 
• 62-53-3 aniline 
• 102-02-3 1-phenylbiguanide 
• 6522-91-4 N-phenyl-guanidine hydrochloride 
• 17356-08-0 thiourea 
• 420-04-2 CYANAMID 
• 7732-18-5 water 
• 1071-37-0 2-ethylisothiourea hydrobromide 
• 103-85-5 monophenylthiourea 
• 129082-86-6 N-phenylthiourea dioxide 
• 1027175-55-8 C₂₂H₁₈N₂O₂S 
• 19503-22-1 1H-benzotriazole-1-carboxamidine hydrochloride 

Downstream Products

• 57356-49-7 phenyl-pyrimidin-2-yl-amine 
• 101269-02-7 5-ethyl-2-anilino-5-butyl-1H-pyrimidine-4,6-dione 
• 102660-99-1 phenylcarbamimidoyl-amidophosphoric acid dibenzyl ester 
• 102319-15-3 phenylcarbamimidoyl-amidophosphoric acid bis-(4-nitro-benzyl ester) 
• 90563-33-0 N-methyl-N'-phenylcarbamimidoyl-thiourea 
• 101599-91-1 5-ethyl-2-anilino-5-isopentyl-1H-pyrimidine-4,6-dione 
• 109813-20-9 phenylcarbamimidoyl-amidophosphoric acid diphenyl ester 
• 66940-97-4 5,5-diethyl-2-anilino-1H-pyrimidine-4,6-dione 
• 101260-15-5 phenylcarbamimidoyl-amidophosphoric acid diisobutyl ester 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 77407-40-0 N-4,5-triphenyl-1H-imidazol-2-amine 
• 136437-05-3 C₁₅H₂₁N₃O₄ 
• 79680-50-5 2-Amino-5,6-dihydro-1,5,6-trans-triphenyl-4(1H)-pyrimidinon 
• 170747-16-7 N-(6-chloro-1,1-dioxo-7-methyl-1,4,2-benzodithiazin-3-yl)-N'-phenylguanidine 

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.

One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation

A bio-inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1-substituted derivatives. This cascade features a 2-aminoimidazole formation that is modeled after an arginine post-translational modification and an aza-electrocyclization. It can be effectively carried out in a one-pot procedure from simple anilines or guanidines, leading to structural analogues of ageladine A that had been otherwise synthetically inaccessible. We found that some compounds out of this structurally novel library show a significant activity in modulating the neural differentiation. Namely, these compounds selectively activate or inhibit the differentiation of neural stem cells to neurons, while being negligible in the differentiation to astrocytes. This study represents a successful case in which the native biofunction of a natural product could be altered by structural modifications.

Reaction of quinones and guanidine derivatives: Simple access to bis-2-aminobenzimidazole moiety of benzosceptrin and other benzazole motifs

A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1′,2′:4,5]imidazo[1,2-a] pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.