154594-16-8

Basic information

• Product Name: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)
• Synonyms: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI);4-(4-HYDRAZINOPHENYL)-1,2,4-TRIAZOLEHYDROCHLORIDE;4H-1,2,4-Triazole,4-(4-hydrazinylphenyl)-;4-(4-hydrazinylphenyl)-4H-1,2,4-triazole;4-(4-Hydrazinophenyl)-4H-1,2,4-triazole
• CAS NO: 154594-16-8
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.19
• Product Categories: HYDRAZINE
• Mol File: 154594-16-8.mol

Chemical Properties

• Boiling Point: 410.1°C at 760 mmHg
• Flash Point: 201.8°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 6.16E-07mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: 2-8°C
• PKA: 4.88±0.30(Predicted)
• CAS DataBase Reference: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(154594-16-8)
• EPA Substance Registry System: 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI)(154594-16-8)

Safety Data

• Hazardous Substances Data: 154594-16-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) is used as a building block for the synthesis of pharmaceutical drugs due to its ability to contribute to the development of bioactive molecules. Its unique structure makes it a valuable candidate for medicinal chemistry and drug discovery, potentially leading to the creation of new therapeutic agents.
Used in Agricultural Industry:
In the agricultural sector, 4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) serves as a precursor for the synthesis of agrochemicals. Its incorporation into the development of new pesticides or other agricultural chemicals can enhance crop protection and yield.
Used in Material Science:
4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) is utilized in the development of new materials due to its structural properties. Its potential role in material science could lead to advancements in various applications, including but not limited to, coatings, adhesives, or other industrial materials.
Used as a Catalyst in Organic Reactions:
4H-1,2,4-Triazole,4-(4-hydrazinophenyl)-(9CI) also has potential applications as a catalyst in organic synthesis. Its unique structure may facilitate or enhance specific chemical reactions, making it a useful tool in the synthesis of complex organic molecules.

InChI:InChI=1/C8H9N5/c9-12-7-1-3-8(4-2-7)13-5-10-11-6-13/h1-6,12H,9H2

Upstream product

• 52761-74-7 4-(4-aminophenyl)-4H-1,2,4-triazole 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 154594-15-7 N-(4-(4H-1,2,4-triazole-4-yl)phenyl)acetamide 
• 104-04-1 N-(4-Nitrophenyl)acetamide 

Downstream Products

• 177945-83-4 1-{3-[5-(1,2,4-Triazol-4-yl)-1H-indol-3-yl]propyl}-4-[(benzylamino)methyl]piperidine 
• 174609-14-4 4-Benzyl-1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)piperidine Hydrogen Oxalate 

Relevant articles and documents

Triazole derivatives

Triazole derivatives represented by formula (IIA), and salts and prodrug thereof, wherein R1 represents C1-6 alkoxy(C1-6)alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 cycloalkyl(C1-6)alkyl, aryl, aryl(C1-6)alkyl, aryloxy(C1-6)alkyl, aryl(C2-6)alkenyl, aryl(C2-6)alkynyl, C3-7 heterocycloalkyl(C1-6)alkyl, heteroaryl, heteroaryl(C1-6)alkyl, heteroaryl(C2-6)alkenyl or heteroaryl(C2-6)alkynyl, any of which groups may be optionally substituted; are selective agonist of 5-HT1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated. STR1

Indoline and azaindoline derivatives as 5-HT1D alpha receptor agonists

Compounds of formula (I), or a salt or prodrug thereof, wherein Z represents an optionally substituted five-membered heteroaromatic ring selected from furan, thiophene, pyrrole, oxazole, thiazole, isoxazole, isothiazole, imidazole, pyrazole, oxadiazole, thiadiazole, triazole, and tetrazole; E represents a chemical bond or a straight or branched alkylene chain containing from 1-4 carbon atoms; Q represents a straight or branched alkylene chain containing from 1-6 carbon atoms; T represents nitrogen or CH; R1 represents aryl(C1-6)alkyl or heteroaryl(C1-6)alkyl, either of which groups may be optionally substituted; and R2 represents hydrogen or C1-6 alkyl are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists. STR1

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

The design, synthesis, and biological evaluation of a novel series of 3- [2-(pyrrolidin-1-yl)ethyl]-indoles with excellent selectivity for h5-HT(1D) (formerly 5-HT(1Dα)) receptors over h5-HT(1B) (formerly 5-HT(1Dβ)) receptors are described. Clinically effective antimigraine drugs such as Sumatriptan show little selectivity between h5-HT(1D) and h5-HT(1B) receptors. The differential expression of h5-HT(1D) and h5-HT(1B) receptors in neural and vascular tissue prompted an investigation of whether a compound selective for the h5-HT(1D) subtype would have the same clinical efficacy but with reduced side effects. The pyrrolidine 3b was initially identified as having 9-fold selectivity for h5-HT(1D) over h5-HT(1B) receptors. Substitution of the pyrrolidine ring of 3b with methylbenzylamine groups gave compounds with nanomolar affinity for the h5-HT(1D) receptor and 100-fold selectivity with respect to h5-HT(1B) receptors. Modification of the indole 5-substituent led to the oxazolidinones 24a,b with up to 163-fold selectivity for the h5-HT(1D) subtype and improved selectivity over other serotonin receptors. The compounds were shown to be full agonists by measurement of agonist-induced [35S]GTPγS binding in CHO cells expressed with h5-HT receptors. This study suggests that the h5-HT(1D) and h5-HT(1B) receptors can be differentiated by appropriate substitution of the ligand in the region which binds to the aspartate residue and reveals a large binding pocket in the h5-HT(1D) receptor domain which is absent for the h5-HT(1B) receptor. The compounds described herein will be important tools to delineate the role of h5-HT(1D) receptors in migraine.

Piperazine, piperidine and tetrahydropyridine derivative of indol-3-alkyl as 5-HT1D-α agonists

Compounds of formula (I), or a salt or prodrug thereof, wherein Z represents an optionally substituted five-membered heteroaromatic ring selected from furan, thiophene, pyrrole, oxazole, thiazole, isoxazole, isothiazole, imidazole, pyrazole, oxadiazole, thiadiazole, triazole and tetrazole; E represents a chemical bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; Q represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms, optionally substituted in any position by a hydroxy group; T represents nitrogen or CH; U represents nitrogen or C--R2 ; V represents oxygen, sulphur or N--R3 ; --F--G-- represents --CH2--N--, --CH2--CH-- or --CH=C--; R1 represents C3-6 alkenyl, C3-6 alkynyl, aryl(C1-6)alkyl or heteroaryl(C1-6)alkyl, any of which groups may be optionally substituted; and R2 and R3 independently represent hydrogen or C1-6 alkyl are selective agonists of 5-HT1D receptors, being potent agonists of the human 5-HT1Dalpha receptor subtype, while possessing at least a 10-fold selective affinity for the 5-HT1Dalpha receptor subtype, relative to the 5-HT1Dbeta subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, while eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.

Azetidine, pyrrolidine and piperidine derivatives

A class of substituted azetidine, pyrrolidine and piperidine derivatives are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.

PIPERAZINE DERIVATIVES AS 5-HT1 AGONISTS

A class of substituted piperazine derivatives of formula I STR1 are selective agonists of 5-HT 1-like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated conditions, for which a selective agonist of these receptors is indicated.

4-substituted 1,2,4-triazole derivatives

A discrete class of 4-substituted 1,2,4-triazole derivatives are selective agonists of 5-HT 1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

Five-membered heteroaromatic compounds as 5-HT receptor agonists

A class of substituted five-membered heteroaromatic compounds are selective agonists of 5-HT 1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.

Imidazole, Triazole and tetrazole derivatives

Imidazole, triazole and tetrazole derivatives of formula (I) are selective agonists of 5-HT1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated, wherein the broken circle represents two non-adjacent double bonds in any position in the five-membered ring; two, three or four of V, W, X, Y and Z represent nitrogen and the remainder represent carbon provided that, when two of V, W, X, Y and Z represent nitrogen and the remainder represent carbon, then the said nitrogen atoms are in non-adjacent positions within the five-membered ring; E represents a bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms; F represents a group of formula (a); U represents nitrogen or C--R2 ; B represents oxygen, sulphur or N--R3 ; R1 represents a group of formula (i), (ii) or (iii).

The chemical evolution of N,N-dimethyl-2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethylamine (L-741,604) and analogues: Potent and selective agonists for 5-HT(1D) receptors

Optimisation of a series of 5-(heterocyclyl)tryptamines led to the identification of the symmetrically substituted, N-4 linked 1,2,4-triazole as the best indole C-5 substituent for 5-HT(1D) receptor affinity and selectivity. The triazole (8) is the most potent and selective, orally bioavailable, 5-HT(1D) receptor agonist identified to date, showing an order of magnitude greater potency than the clinical compound sumatriptan with improved subtype selectivity.