119192-10-8

Basic information

• Product Name: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline
• Synonyms: 1-(4-Aminobenzyl)-1H-1,2,4-triazole;4-(1H-1,2,4-Triazol-1-ylmethyl)aniline 97%;4-(1H-1,2,4-triazol-1-ylmethyl)-benzenamine( For Rizatriptan );4-[1H-1,2,4-TRIAZOLE-1-YL METHYL]BENZENE AMINE (FOR RIZATRIPTAN);1-(4-Aminophenyl)methyl-1,2,4-Triazole see also 4-(1H-1,2,4-Triazol-1-yl-Methyl)Benzenamine;1-(4-AMINOBENZYL)-1,2,4-TRIAZOL;Benzenamine, 4-(1H-1,2,4-triazol-1-ylmethyl);AIDS339154
• CAS NO: 119192-10-8
• Molecular Formula: C₉H₁₀N₄
• Molecular Weight: 174.2
• EINECS: 1806241-263-5
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;Chemical Amines;Intermediates of Rizatriptan;Amine;Aromatics;Heterocycles;Phenyls & Phenyl-Het
• Mol File: 119192-10-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 402.1 °C at 760 mmHg
• Flash Point: 197 °C
• Appearance: White to pale yellow/Powder
• Density: 1.26 g/cm³
• Vapor Pressure: 1.12E-06mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.42±0.10(Predicted)
• CAS DataBase Reference: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(119192-10-8)
• EPA Substance Registry System: 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(119192-10-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-41-37/38
• Safety Statements: 22-26-36/37/39
• HazardClass: 6.1
• Hazardous Substances Data: 119192-10-8(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Different sources of media describe the Uses of 119192-10-8 differently. You can refer to the following data:
1. Rizatriptan intermediate
2. 4-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine is an intermediate useful in organic synthesis and other chemical processes.

InChI:InChI=1/C9H10N4/c10-9-3-1-8(2-4-9)5-13-7-11-6-12-13/h1-4,6-7H,5,10H2

Synthetic route

1-(4-nitrophenyl)methyl-1,2,4-triazole (119192-09-5) → 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8)

Conditions	Yield
With hydrogenchloride; palladium-carbon In ethanol; water; ethyl acetate	100%
With hydrogenchloride; palladium-carbon In ethanol; water; ethyl acetate	100%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;	96%

aniline hydrochloride (142-04-1) + 1-(hydroxymethyl)-1,2,4-triazole (74205-82-6) → 4,4'-diamino diphenyl methane (101-77-9) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8)

Conditions	Yield
With acetic acid for 0.0833333h; Heating;	A 10% B 59%

4-nitrobenzyl chloride (100-14-1) + SO2 → 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / sodium ethoxide / ethanol / room temp. 4 h, reflux, 1 h 2: 96 percent / hydrogen / 5percent Pd/C / ethanol / Ambient temperature View Scheme

4-amino-1-(4-nitrobenzyl)-1,2,4-triazolium bromide (6085-99-0) → 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C 2: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr View Scheme

1-bromomethyl-4-nitro-benzene (100-11-8) → 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / ethanol / 4 h / Heating 2: 65 percent / 10percent aq NaNO2 / aq. HCl / 0 °C 3: 80 percent / H2 / 10percent Pd-C / ethyl acetate / 60 °C / 760 Torr View Scheme

4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) + 1-(tetrazol-2-ylmethyl)-4-nitrobenzene (144035-43-8) → 2-(4-Aminophenyl)methyl-1,2,3,4-tetrazole

Conditions	Yield
	100%

4-Trifluoromethylbenzaldehyde (455-19-6) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-(trifluoromethyl)phenyl)thiazolidin-4-one (1388155-36-9)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 4h;	97%

2-formyl oxine (14510-06-6) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → C19H15N5O

Conditions	Yield
With acetic acid In toluene Molecular sieve; Reflux; Inert atmosphere;	96%

4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine (160194-26-3) + 3,5-diiodo-4-aminobenzyltriazole

Conditions	Yield
With Iodine monochloride; calcium carbonate In methanol; water	A 91% B 3%

4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine (160194-26-3)

Conditions	Yield
With iodine; sodium hydrogencarbonate In water for 30h;	90%
With Iodine monochloride; calcium carbonate
With Iodine monochloride; calcium carbonate

n-perfluorohexyl iodide (355-43-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4-((1H-1,2,4-triazol-1-yl)methyl)-2-(perfluorohexyl)aniline

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;	90%

4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 1-(p-hydroxybenzyl)-1,2,4-triazole (119192-11-9)

Conditions	Yield
With sodium nitrate; sulfuric acid In water room temp., 20 min, 85 deg C, 35 min;	88%

1-chloro-7-hydroxy-4-nitro-9(10H)-acridinone (99009-49-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 1-((4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)amino)-7-hydroxy-4-nitroacridin-9(10H)-one

Conditions	Yield
With caesium carbonate In 1,4-dioxane for 9h; Heating;	87.6%

phthalic anhydride (85-44-9) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 2-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}carbamoyl)benzoic acid

Conditions	Yield
In acetone at 20℃; for 1h;	86%
In acetone at 20℃; for 1h;

Togni's reagent II (887144-94-7) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4-((1H-1,2,4-triazol-1-yl)methyl)-2-(trifluoromethyl)aniline (1558046-39-1)

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation;	82%
With tris[2-phenylpyridinato-C2,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation; Schlenk technique;	80%

benzaldehyde (100-52-7) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-phenylthiazolidin-4-one (1388155-35-8)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 7h;	81%

4-methyl-benzaldehyde (104-87-0) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-p-tolylthiazolidin-4-one (1388155-37-0)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 11h;	80%

4-chlorobenzaldehyde (104-88-1) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(4-chlorophenyl)thiazolidin-4-one (1388155-38-1)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 7h;	79%

mercaptoacetic acid (68-11-1) + 3-Chlorobenzaldehyde (587-04-2) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(3-chlorophenyl)thiazolidin-4-one (1388155-39-2)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 7h;	78%

2-chloro-benzaldehyde (89-98-5) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 3-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2-(2-chlorophenyl)thiazolidin-4-one (1388155-40-5)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 7h;	76%

salicylaldehyde (90-02-8) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 2-[2-(4-[1,2,4]triazol-1-ylmethylphenyl)iminomethylphenol]

Conditions	Yield
With acetic acid In ethanol at 65 - 70℃; for 6h;	76%

Ethyl bromodifluoroacetate (667-27-6) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 5-((1H-1,2,4-triazol-1-yl)methyl)-3,3-difluoroindolin-2-one

Conditions	Yield
Stage #1: Ethyl bromodifluoroacetate; 4-(1H-1,2,4-triazol-1-ylmethyl)aniline With tris[2-phenylpyridinato-C2,N]iridium(III); sodium carbonate In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; Sealed tube; Stage #2: With ethanol at 60℃; for 6h;	74%

1-(1H-benzo[f]chromen-2-yl)-2,2,2-trifluoroethan-1-one + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → (E)-1,1,1-trifluoro-3-[(2-hydroxynaphth-1-yl)methyl]-4-({4-[(1H-1,2,4-triazol-1-yl)methyl]phenyl}amino)but-3-en-2-one

Conditions	Yield
In methanol at 20℃; for 4h; stereoselective reaction;	74%

4-nitrobenzaldehdye (555-16-8) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → (4-nitrobenzylidene)-(4-[1,2,4]triazol-1-ylmethylphenyl)amine (127988-32-3)

Conditions	Yield
With acetic acid In ethanol at 65 - 70℃; for 6h;	72%
In ethanol; benzene for 24h; Heating;	58%

cadmium(II) perchlorate hexahydrate + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → {[Cd(1-(4-aminobenzyl)-1H-1,2,4-triazole)2(H2O)2]*(ClO4)2*H2O}n

Conditions	Yield
In methanol; water for 0.5h;	69%

C24H17NO4 + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4'-{2-oxo-3-[(4-[1,2,4]triazol-1-ylmethyl-phenyl-imino)-methyl]-2H-quinolin-1-ylmethyl}-biphenyl-2-carboxylic acid (1599479-42-1)

Conditions	Yield
In methanol Reflux;	65.2%

C24H17N5OS + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → {2-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethylsulphanyl]-quinolin-3-ylmethylene}-(4-[1,2,4]triazol-1-ylmethyl-phenyl)-amine (1599479-49-8)

Conditions	Yield
In methanol Reflux;	63.7%

cyclohexanone (108-94-1) + mercaptoacetic acid (68-11-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 4-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-1-thia-4-azaspiro[4.5]decan-3-one (1388155-31-4)

Conditions	Yield
In polypropylene glycol-2000 at 110℃; for 11h;	60%

4-chlorobenzaldehyde (104-88-1) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → N-(4-chlorobenzal)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine (127988-30-1)

Conditions	Yield
In ethanol; benzene for 24h; Heating;	59%

2,4,6-triphenylpyrylium tetrafluoroborate (448-61-3) + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 1-(4-((1H-1,2,4-triazol-1-yl)methyl)phenyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

Conditions	Yield
In ethanol at 85 - 90℃; for 4h; Schlenk technique;	57%

silver perchlorate + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → [Ag2(μ2-1-(4-aminobenzyl)-1,2,4-triazole)(μ3-1-(4-aminobenzyl)-1,2,4-triazole)(perchlorate)].(perchlorate)

Conditions	Yield
In methanol; water at 160℃; for 12.5h; Autoclave;	53%

water (7732-18-5) + silver nitrate + 4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → C9H10N4*Ag(1+)*NO3(1-)*0.125H2O

Conditions	Yield
In methanol at 160℃; for 12h; Autoclave;	53%

Upstream product

• 119192-09-5 1-(4-nitrophenyl)methyl-1,2,4-triazole 
• 142-04-1 aniline hydrochloride 
• 74205-82-6 1-(hydroxymethyl)-1,2,4-triazole 
• 100-14-1 4-nitrobenzyl chloride 
• 6085-99-0 4-amino-1-(4-nitrobenzyl)-1,2,4-triazolium bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 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 
• 127988-32-3 N-(4-nitrobenzal)-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 
• 119192-11-9 1-(p-hydroxybenzyl)-1,2,4-triazole 
• 160194-26-3 4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine 
• 160194-39-8 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol 
• 144034-80-0 rizatriptan 
• 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 
• 127988-41-4 N-(2,4-dichlorobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 127988-44-7 N-(4-nitrobenzyl)-4-(1H-1,2,4-triazol-1-ylmethyl)benzeneamine 
• 154748-67-1 (4-[1,2,4]triazol-1-ylmethylphenyl)hydrazine hydrochloride 
• 1092370-41-6 4-(1,2,4-triazol-1-yl-methyl)phenyl-diazonium chloride 

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