20271-35-6

Basic information

• Product Name: 1H-1,2,3-Triazole-4-carbonitrile, 5-amino-1- (phenylmethyl)-
• Synonyms: 1H-1,2,3-Triazole-4-carbonitrile, 5-amino-1- (phenylmethyl)-
• CAS NO: 20271-35-6
• Molecular Formula: C₁₀H₉N₅
• Molecular Weight: 199.216
• Mol File: 20271-35-6.mol

Chemical Properties

• Melting Point: 184 °C(Solv: water (7732-18-5))
• Boiling Point: 472.9°C at 760 mmHg
• Flash Point: 239.8°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 4.11E-09mmHg at 25°C
• Refractive Index: 1.689
• PKA: -2.13±0.13(Predicted)
• CAS DataBase Reference: 1H-1,2,3-Triazole-4-carbonitrile, 5-amino-1- (phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-Triazole-4-carbonitrile, 5-amino-1- (phenylmethyl)-(20271-35-6)
• EPA Substance Registry System: 1H-1,2,3-Triazole-4-carbonitrile, 5-amino-1- (phenylmethyl)-(20271-35-6)

Safety Data

• Hazardous Substances Data: 20271-35-6(Hazardous Substances Data)

Usage

Structure

1H-1,2,3-triazole-4-carbonitrile, 5-amino-1-(phenylmethyl)-

Functional groups

carbonitrile, amino

Attachment position

amino group at position 5

Usage

intermediate in the synthesis of pharmaceuticals and agrochemicals

Potential applications

development of new drugs

Building block

versatile for the synthesis of biologically active molecules

Stability

triazole ring structure enhances potential for chemical transformations

InChI:InChI=1/C10H9N5/c11-6-9-10(12)15(14-13-9)7-8-4-2-1-3-5-8/h1-5H,7,12H2

Upstream product

• 622-79-7 benzyl azide 
• 75-05-8 acetonitrile 
• 109-77-3 malononitrile 
• 941-55-9 4-toluenesulfonyl azide 
• 4342-08-9 4-amino-3-benzyl-1,2,3-triazole-5-carboxamide 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 

Downstream Products

• 1256556-23-6 3-benzyl-7-chloro-5-(4-nitro-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 94079-02-4 5-Amino-N-benzoyl-1-benzyl-1,2,3-triazol-4-carboxamidin 
• 94079-01-3 5-amino-1-benzyl-4-(5-phenyl-1,2,4-oxadiazol-3-yl)-1,2,3-triazole 
• 116564-63-7 3-Benzyl-5,7-dimethyl-3H-1,2,3-triazolo<4,5-e>-<1,2,4>triazolo<1,5-c>pyrimidin 
• 116564-62-6 3-Benzyl-5-methyl-3H-1,2,3-triazolo<4,5-e>-<1,2,4>triazolo<1,5-c>pyrimidin 
• 116564-61-5 3-Benzyl-7-methyl-3H-1,2,3-triazolo<4,5-e>-<1,2,4>triazolo<1,5-c>pyrimidin 
• 116564-56-8 3-Benzyl-5-methyl-3,6-dihydro-7-imino-3H-1,2,3-triazolo<4,5-d>pyrimidin-6-amin 
• 116564-60-4 3-Benzyl-3H-1,2,3-triazolo<4,5-e>-<1,2,4>triazolo<1,5-c>pyrimidin 
• 116564-55-7 3-Benzyl-3,6-dihydro-7-imino-3H-1,2,3-triazolo<4,5-d>pyrimidin-6-amin 
• 94079-03-5 4-Amino-1-benzyl-6-phenyl-1H-1,2,3-triazolo<4,5-d>pyrimidin 
• 77976-40-0 3-benzyl-4-oxamoylamino-3H-1,2,3-triazole-5-carbonitrile 
• 77976-42-2 4-amino-3-benzyl-5-oxamoylaminomethyl-3H-1,2,3-triazole 
• 94078-83-8 5-Amino-1-benzyl-1,2,3-triazol-4-carboxamidoxim 
• 103912-97-6 1-benzyl-4-cyano-5-chloro-1,2,3-triazole 

Relevant articles and documents

Energetic derivatives of 5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole

This study presents the preparation of the novel nitrogen-rich compound 5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole (5) from commercially available chemicals in a five step synthesis. The more energetic derivatives with azido (6) and nitro (7) groups, as well as a diazene bridge (8) were also successfully prepared. The energetic compounds were comprehensively characterized by various means, including vibrational (IR, Raman) and multinuclear (1H, 13C, 14N, 15N) NMR spectroscopy, mass spectrometry and differential thermal analysis. The sensitivities towards important outer stimuli (impact, friction, electrostatic discharge) were determined according to BAM standards. The enthalpies of formation were calculated on the CBS-4M level of theory, revealing highly endothermic values, and were utilized to calculate the detonation parameters using EPXLO5 (6.02).

β-(Cycloalkylamino)ethanesulfonyl azides as novel water-soluble reagents for the synthesis of diazo compounds and heterocycles

[Figure not available: see fulltext.] Novel water-soluble sulfonyl azides were synthesized, which are basic by nature. The obtained compounds were used as donors of the diazo group in the diazo transfer reaction. Due to their good solubility in water and high polarity, the byproducts formed in this case were easily separated from the desired products by washing with water or column chromatography. It was also shown that new sulfonyl azides as a result of reactions can be incorporated in heterocyclic products, imparting them water solubility.

2,4,6,7-TETRAHYDRO-PYRAZOLO[4,3-D]PYRIMIDIN-5-ONE DERIVATIVES AND RELATED COMPOUNDS AS C5A RECEPTOR MODULATORS FOR TREATING VASCULITIS AND INFLAMMATORY DISEASES

The present invention relates to derivatives of formula (I) wherein Ring A, X, Y, Z, RA, R1, R2, R3 and R4 are The present invention discloses derivatives of formula (I), wherein Ring A, X, Y, Z, RA, R1, R2, R3 and R4 are as described in the description, and in particular e.g. 2,4,6,7-tetrahydro-pyrazolo[4,3- d]pyrimidin-5-one derivatives and related compounds, their preparation, pharmaceutically acceptable salts thereof, their use as pharmaceuticals, pharmaceutical compositions containing one or more compounds of formula (I), and especially their use as C5a receptor modulators for treating e.g. vasculitis and inflammatory diseases.

An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.

A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.

SYNTHESIS OF 5-DIAZOMETHYL SUBSTITUTED v-TRIAZOLOPYRIMIDINES

The condensation of 5-azido-4-cyano-1-substituted-1,2,3-triazoles with active methylene nitriles in the presence of a strong base yields the title compounds 6 which exist in equilibrium with the tricyclic systems 5.The equilibrium position is shifted towa