119192-09-5

Basic information

• Product Name: 1-(4-Nitrophenyl)methyl-1,2,4-triazole
• Synonyms: 1-(4-NITROPHENYL)METHYL-1,2,4-TRIAZOLE;1-[(4-NITROPHENYL)METHYL]-1H-1,2,4-TRIAZOLE;1-(4-NITROBENZYL)-1,2,4-TRIAZOLE;1-(4-NITROBENZYL)-1H-[1,2,4]TRIAZOLE;1H-1-[(4-Aminophenyl)methyl][1,2,4]triazole;1H-1,2,4-Triazole,1-[(4-nitrophenyl)methyl]-;Nitrobenzyltriazole
• CAS NO: 119192-09-5
• Molecular Formula: C₉H₈N₄O₂
• Molecular Weight: 204.19
• Mol File: 119192-09-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 100.0 to 104.0 °C
• Boiling Point: 433.368 °C at 760 mmHg
• Flash Point: 215.893 °C
• Appearance: /
• Density: 1.398 g/cm³
• Vapor Pressure: 1.03E-07mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 2.46±0.10(Predicted)
• CAS DataBase Reference: 1-(4-Nitrophenyl)methyl-1,2,4-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Nitrophenyl)methyl-1,2,4-triazole(119192-09-5)
• EPA Substance Registry System: 1-(4-Nitrophenyl)methyl-1,2,4-triazole(119192-09-5)

Safety Data

• Hazardous Substances Data: 119192-09-5(Hazardous Substances Data)

Usage

Description

1-(4-Nitrophenyl)methyl-1,2,4-triazole is an organic compound that is characterized by its unique chemical structure, which includes a triazole ring and a nitrophenylmethyl group. 1-(4-Nitrophenyl)methyl-1,2,4-triazole is known for its potential applications in various fields due to its chemical properties.

Uses

1. Used in Pharmaceutical Industry:
1-(4-Nitrophenyl)methyl-1,2,4-triazole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
2. Used in Method for Preparing Rizatriptan Benzoate Intermediate:
In the pharmaceutical industry, 1-(4-Nitrophenyl)methyl-1,2,4-triazole is specifically utilized as a crucial intermediate in the preparation of Rizatriptan Benzoate, a medication used to treat migraine headaches. Its role in this process highlights its importance in the development of effective treatments for various medical conditions.

InChI:InChI=1/C9H8N4O2/c14-13(15)9-3-1-8(2-4-9)5-12-7-10-6-11-12/h1-4,6-7H,5H2

Upstream product

• 288-88-0 1,2,4-Triazole 
• 100-14-1 4-nitrobenzyl chloride 
• 6085-99-0 4-amino-1-(4-nitrobenzyl)-1,2,4-triazolium bromide 
• 41253-21-8 sodium triazole 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 288-88-0 1,2,4-Triazole 
• 584-13-4 4-amino-1,2,4-triazole 
• 7440-44-0 pyrographite 
• 40970-34-1 1-(4-nitrophenylmethyl)-4-amino-4H-1,2,4-triazolium chloride 

Downstream Products

• 119192-10-8 4-(1H-1,2,4-triazol-1-ylmethyl)aniline 
• 144235-64-3 4-(1,2,4-triazolylmethyl)phenylamine hydrochloride 
• 144035-23-4 2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine 
• 144035-22-3 4-(1,2,4-triazol-1-ylmethyl)phenylhydrazine 
• 119192-11-9 1-(p-hydroxybenzyl)-1,2,4-triazole 
• 127988-31-2 N-(4-fluorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-30-1 N-(4-chlorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-43-6 N-(4-fluorobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-42-5 N-(4-chlorobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-29-8 N-(2,4-dichlorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-41-4 N-(2,4-dichlorobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-32-3 N-(4-nitrobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-44-7 N-(4-nitrobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 

Relevant articles and documents

Taming Ambident Triazole Anions: Regioselective Ion Pairing Catalyzes Direct N-Alkylation with Atypical Regioselectivity

Controlling the regioselectivity of ambident nucleophiles toward alkylating agents is a fundamental problem in heterocyclic chemistry. Unsubstituted triazoles are particularly challenging, often requiring inefficient stepwise protection-deprotection strategies and prefunctionalization protocols. Herein we report on the alkylation of archetypal ambident 1,2,4-triazole, 1,2,3-triazole, and their anions, analyzed by in situ 1H/19F NMR, kinetic modeling, diffusion-ordered NMR spectroscopy, X-ray crystallography, highly correlated coupled-cluster computations [CCSD(T)-F12, DF-LCCSD(T)-F12, DLPNO-CCSD(T)], and Marcus theory. The resulting mechanistic insights allow design of an organocatalytic methodology for ambident control in the direct N-alkylation of unsubstituted triazole anions. Amidinium and guanidinium receptors are shown to act as strongly coordinating phase-transfer organocatalysts, shuttling triazolate anions into solution. The intimate ion pairs formed in solution retain the reactivity of liberated triazole anions but, by virtue of highly regioselective ion pairing, exhibit alkylation selectivities that are completely inverted (1,2,4-triazole) or substantially enhanced (1,2,3-triazole) compared to the parent anions. The methodology allows direct access to 4-alkyl-1,2,4-triazoles (rr up to 94:6) and 1-alkyl-1,2,3-triazoles (rr up to 99:1) in one step. Regioselective ion pairing acts in effect as a noncovalent in situ protection mechanism, a concept that may have broader application in the control of ambident systems.

Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions

The rate constants for the reactions of a variety of nucleophiles reacting with substituted benzyl chlorides in liquid ammonia (LNH3) have been determined. To fully interpret the associated linear free-energy relationships, the ionization constants of phenols ions in liquid ammonia were obtained using UV spectra. These equilibrium constants are the product of those for ion-pair formation and dissociation to the free ions, which can be separated by evaluating the effect of added ammonium ions. There is a linear relationship between the pKa of phenols in liquid ammonia and those in water of slope 1.68. Aminium ions exist in their unprotonated free base form in liquid ammonia and their ionization constants could not be determined by NMR. The rates of solvolysis of substituted benzyl chlorides in liquid ammonia at 25 °C show a Hammett ρ of zero, having little or no dependence upon ring substituents, which is in stark contrast with the hydrolysis rates of substituted benzyl halides in water, which vary 107 fold. The rate of substitution of benzyl chloride by substituted phenoxide ions is first order in the concentration of the nucleophile indicative of a SN2 process, and the dependence of the rate constants on the pKa of the phenol in liquid ammonia generates a Bronsted βnuc = 0.40. Contrary to the solvolysis reaction, the reaction of phenoxide ion with 4-substituted benzyl chlorides gives a Hammett ρ = 1.1, excluding the 4-methoxy derivative, which shows the normal positive deviation. The second order rate constants for the substitution of benzyl chlorides by neutral and anionic amines show a single Bronsted βnuc = 0.21 (based on the aqueous pKa of amine), but their dependence on the substituent in substituted benzyl chlorides varies with a Hammett ρ of 0 for neutral amines, similar to that seen for solvolysis, whereas that for amine anions is 0.93, similar to that seen for phenoxide ion.(Figure Presented)

IMPROVED PROCESS FOR THE PREPARATION OF RIZATRIPTAN BENZOATE

Present invention discloses an improved and commercially viable process for the preparation of rizatriptan benzoate of formula (I). According to the present process the hydrazone intermediate derived from the phenylhydrazine of formula- (III) and 4- dimethylaminobutyraldehyde diethyl acetal is gradually heated to 60-70 °C in aqueous sulfuric acid medium and maintained for 3-4hr to get rizatriptan with less dimeric impurity of formula (X). The resultant rizatriptan is isolated and converted into the pharmaceutically acceptable benzoate salt. Present process produces less percentage of dimeric (less than 3 %) or polymeric impurities compared to the prior art process and more yield of rizatriptan. Rizatriptan benzoate produced according to the present process has more than 99.5 % purity with less than 0.1% dimeric impurity of formula (X) by HPLC. Rizatriptan benzoate is useful for the treatment of migraine.