101-01-9

Basic information

• Product Name: 1,2,3-TRIPHENYLGUANIDINE
• Synonyms: 1,2,3-trifenylguanidin;1,2,3-triphenyl-guanidin;n,n’,n’’-triphenyl-guanidin;N,N',N''-TRIPHENYLGUANIDINE;TRIPHENYLGUANIDINE;A-TRIPHENYLGUANIDINE;1,2,3-TRIPHENYLGUANIDINE;«
• CAS NO: 101-01-9
• Molecular Formula: C₁₉H₁₇N₃
• Molecular Weight: 287.36
• EINECS: 202-907-9
• Mol File: 101-01-9.mol

Chemical Properties

• Melting Point: 146-147°C
• Boiling Point: 419.66°C (rough estimate)
• Appearance: /
• Density: 1,16 g/cm3
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.10±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 1,2,3-TRIPHENYLGUANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-TRIPHENYLGUANIDINE(101-01-9)
• EPA Substance Registry System: 1,2,3-TRIPHENYLGUANIDINE(101-01-9)

Safety Data

• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-36/37
• RTECS: MF6825000
• TSCA: Yes
• Hazardous Substances Data: 101-01-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3-Triphenylguanidine is used as an intermediate for organic synthesis, serving as a building block for the development of various organic compounds and materials.
Used in Rubber Industry:
1,2,3-Triphenylguanidine is used as an accelerator for the vulcanization of rubber. It enhances the process by promoting the formation of cross-links between rubber molecules, resulting in improved strength, elasticity, and durability of the final rubber product.
Chemical Properties:
1,2,3-Triphenylguanidine is a white, crystalline powder with combustible properties. Its chemical structure and reactivity make it a valuable compound in various applications across different industries.

Purification Methods

Crystallise the guanidine from EtOH or EtOH/water. Dry it in vacuo.[Beilstein 12 H 451, 12 I 261, 12 II 246, 12 III 907, 12 IV 866.]

Upstream product

• 110-89-4 piperidine 
• 3898-08-6 1,1-diphenylthiourea 
• 110-86-1 pyridine 
• 102-08-9 N,N-diphenylthiourea 
• 14124-22-2 2-(Phenylimino)-1,3-diphenyl-1,3-diazetidin-4-one 
• 62-53-3 aniline 
• 19018-13-4 bis-(α'-oxo-bibenzyl-α-ylidene)-[1,3]dithietane 
• 76402-03-4 2-N-phenyl-N-(phenylamino-phenyliminomethyl)aminobenzothiazole 
• 60-29-7 diethyl ether 
• 594-42-3 chlorothio-trichloro-methane 
• 2314-48-9 (S,S)-dimethyl trithiocarbonate 
• 64-17-5 ethanol 
• 67-66-3 chloroform 
• 13029-19-1 trichloro-methanesulfenic acid dimethylamide 

Downstream Products

• 14124-22-2 2-(Phenylimino)-1,3-diphenyl-1,3-diazetidin-4-one 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 62-53-3 aniline 
• 622-16-2 1,3-Diphenylcarbodiimide 
• 102-07-8 bis(diphenyl)urea 
• 107263-37-6 7-anilino-6-phenyl-5,12-diazabenzanthracene 
• 4250-94-6 7-anilino-6-(4-tolyl)-5,12-diazabenzanthracene 
• 5416-43-3 (5-anilino-2,4-diphenyl-2,4-dihydro-[1,2,4]triazol-3-ylidene)-phenyl-amine 
• 77903-04-9 N¹,N²,N³,N⁴,N⁵-Pentaphenylbiguanide 
• 751-59-7 (6-naphthalen-2-yl-dibenzo[b,h][1,6]naphthyridin-7-yl)-phenyl-amine 
• 18557-23-8 [3-(3-nitro-phenyl)-4-phenyl-4H-[1,2,4]oxadiazol-5-ylidene]-phenyl-amine 
• 64850-97-1 N-Fluorenyl-N,N',N''-triphenylguanidin 
• 94562-27-3 4-oxo-1,3-diphenyl-2-phenylimino-1,3,7,8-tetra-azaspiro<4.5>deca-6,9-diene-10-carboxylic acid 
• 77586-21-1 2,3-dihydro-1,3-diphenyl-2-phenyliminopyrimidin-4(1H)-one 

Relevant articles and documents

Novel Desulphurization of Thiourea Derivatives by Alkaline Autoxidation

Autoxidation of 1,3-disubstituted thioureas in the presence of oxygen and tertiary butoxide in tertiary butanol afforded the corresponding ureas in good yields together with small amounts of the corresponding guanidines while the same treatment of benz- or naphth-imidazole-2-thiones gave the parent imidazoles and the 2-sulphonic acids.

Mechanistic insights into N - N bond cleavage in catalytic guanylation reactions between 1,2-diarylhydrazines and carbodiimides

Cleavage of the N - N bond in 1,2-diarylhydrazine was achieved through an alkyllithium-catalyzed guanylation reaction of 1,2-diarylhydrazine with carbodiimide, affording guanidine and azo compounds. This N - N bond cleavage via thermal rearrangement was d

INVESTIGATION OF THE THERMOLYSIS OF 5-METHYL-1-PHENYLTETRAZOLE BY COMBINED DERIVATOGRAPHY AND MASS SPECTROMETRY

The thermolysis of 5-methyl-1-phenyltetrazole was studied at 20-350 deg C by derivatography and mass spectrometry, and it was shown that thermal decomposition proceeds with the elimination of a molecule of nitrogen and is accompanied by skeletal rearrangement of the intermediately formed nitrene to 2-methylbenzimidazole or migration of the methyl group to the nitrogen atom with the formation of methylphenylcarbodiimide (MPCD).In addition, symmetrical dimethyl- and diphenylcarbodiimides, methylphenylguanidines, and aniline are formed.It is assumed that the formation of these compounds in pyrolyzate is due to polymerization of MPCD and subsequent thermal destruction of the polymerization products.A scheme for the thermolysis of 5-methyl-1-phenyltetrazole is proposed.

Molecular structure and acid/base properties of 1,2-dihydro-1,3,5-triazine derivatives

It is shown that guanidine and its N,N-dimethyl-derivative react with substituted carbodiimides, affording hitherto unknown 1,2-dihydro-1,2,3-triazine derivatives. The structures of three novel compounds of this type and their perchlorate salts were elucidated by spectroscopic (IR, 1H and 13C NMR and 15N solid-state NMR) and X-ray diffraction methods. The acid/base properties were also determined experimentally and by using DFT calculations with the B3LYP functional. The most basic compound was found to be dihydrotriazine 3, the basicity of which with the pKa value of 23.3 is of the same order of magnitude as that of tetramethylguanidine. Acidity measurements revealed that all the compounds studied are very weak acids with pKa values in the range of 25.8-30.8 pKa units in acetonitrile. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

O-Iodoxybenzoic acid mediated oxidative condensation: Synthesis of guanidines using 1,-3-disubstituted thiourea precursors

An efficient and mild oxidative condensation procedure using o-iodoxybenzoic acid and triethylamine or ammonia as base has been developed for the synthesis of guanidines starting from easily synthesizable 1,3-disubstituted thioureas and amines or ammonia.

Synthesis and some transformations of (dialkoxy)arylimidophosphinoylformamidines

Dialkyl hydrogen phosphites add reversibly to dicyclohexylcarbodiimide, forming N,N'-dicyclohexylformamidines.Similar addition products derived from phenylphophoramidites and diphenylcarbodiimide are converted on heating or on prolonged storage at room temperature into 1-dialkoxyphosphino-1,2,3-triphenylguanidines together with other products; their hydrolysis gives anilidophosphates and diphenylformamidine, and under the action of dithiophosphoric acids they lose both alkyl groups, yielding zwitterionic anilido(formamidinio)phosphonates.

Benzenetellurinic Mixed Anhydrides as Mild Oxidizing Agents

Three benzenetellurinic mixed anhydrides. i. e. benzenetellurinyl acetate, trifluoroacetate, and trifluoromethanesulfonate, have been found to be mild oxidizing agents for various substrates such as thiol, phosphine, acyloin, α-hydroxy ester, catechol, hydroquinone, thiourea, and thioamide.The reactions towards the last two substrates are highly chemoselective, depending on both the reagent and substrate.

Photochemical Reactions of Primary Aromatic Amines with Chloromethanes in Solution. II. The Products and Mechanisms of Partial Reactions of Aniline in Tetrachloromethane, Chloroform and Dichloromethane

Major products of photochemical reactions of aniline in tetrachloromethane, chloroform and dichloromethane have been isolated and identified.The mechanisms of partial reactions have been discussed. - Keywords: Photochemical Reactions, Primary Aromatic Amines, Chloromethanes

Exchange, Elimination, and Ring Opening Reactions of 2,3-Dihydrobenzimidazothiadiazoles and 3H-Benzimidazodithiazoles

The reactions of benzimidazothiadiazol-3(2H)-ones (1) with isocyanates, isothiocyanates, carbon disulphide, aryl cyanates, acetylenedicarboxylates, and enamines, with exchange of the isocyanate component of (1), to give the corresponding condensed benzimidazole derivatives (1)-(6) are described.Under more severe conditions the 1-benzothiazol-2-yl-1,3-dihydrobenzimidazole-2-thiones (7) were obtained from aromatic isothiocyanates.Thermolysis of the thiadiazoles (1) led to the triazine derivative (12) with elimination of isocyanate and sulphur, and in the presence of phenols to the 2-aryloxybenzimidazoles (13).With amines and CH-acidic compounds, the S,N bond in compound (1) was cleaved to give benzimidazol-2-ylsulphenamides (14), and the ω-substituted methylthiobenzimidazoles (17) and (18).With cyanide ion, insertion into the S,N bond of compound (1) to furnish the thiadiazine (22) took place.The dithiazoles (2) were fragmented by amines to give 1,3-dihydrobenzimidazole-2-thione and guanidine with loss of sulphur; reaction with cyanide ion then gave the dibenzimidazothiadiazine (25).

Novel Desulphurization of 1,3-Disubstituted Thioureas by Superoxide Anion (O2*-): One-step Synthesis of 1,2,3-Trisubstituted Guanidines from 1,3-Disubstituted Thioureas

Treatment of 1,3-diarylthioureas with superoxide anion (O2*-) at 20 deg C in tetrahydrofuran or acetonitrile resulted in the formation of 1,2,3-triarylguanidines in excellent yields.